diff --git a/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/CompareSchemasVisitor.java b/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/CompareSchemasVisitor.java
new file mode 100644
index 000000000000..bb0d32f8f644
--- /dev/null
+++ b/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/CompareSchemasVisitor.java
@@ -0,0 +1,266 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import java.util.List;
+import java.util.Map;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.relocated.com.google.common.collect.Maps;
+import org.apache.iceberg.schema.SchemaWithPartnerVisitor;
+import org.apache.iceberg.types.Type;
+import org.apache.iceberg.types.Types;
+
+/**
+ * Visitor class which compares an input schema to a table schema and emits a compatibility {@link
+ * Result}.
+ *
+ * <ul>
+ *   <li>SAME: The two schemas are semantically identical
+ *   <li>DATA_CONVERSION_NEEDED: We can evolve the data associated with the input schema to match
+ *       the table schema.
+ *   <li>SCHEMA_UPDATE_NEEDED: We need to migrate the table schema to match the input schema.
+ * </ul>
+ *
+ * The input schema fields are compared to the table schema via their names.
+ */
+public class CompareSchemasVisitor
+    extends SchemaWithPartnerVisitor<Integer, CompareSchemasVisitor.Result> {
+
+  private final Schema tableSchema;
+
+  private CompareSchemasVisitor(Schema tableSchema) {
+    this.tableSchema = tableSchema;
+  }
+
+  public static Result visit(Schema dataSchema, Schema tableSchema) {
+    return visit(dataSchema, tableSchema, true);
+  }
+
+  public static Result visit(Schema dataSchema, Schema tableSchema, boolean caseSensitive) {
+    return visit(
+        dataSchema,
+        -1,
+        new CompareSchemasVisitor(tableSchema),
+        new PartnerIdByNameAccessors(tableSchema, caseSensitive));
+  }
+
+  @Override
+  public Result schema(Schema dataSchema, Integer tableSchemaId, Result downstream) {
+    if (tableSchemaId == null) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    return downstream;
+  }
+
+  @Override
+  public Result struct(Types.StructType struct, Integer tableSchemaId, List<Result> fields) {
+    if (tableSchemaId == null) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    Result result = fields.stream().reduce(Result::merge).orElse(Result.SCHEMA_UPDATE_NEEDED);
+
+    if (result == Result.SCHEMA_UPDATE_NEEDED) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    Type tableSchemaType =
+        tableSchemaId == -1 ? tableSchema.asStruct() : tableSchema.findField(tableSchemaId).type();
+    if (!tableSchemaType.isStructType()) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    if (struct.fields().size() != tableSchemaType.asStructType().fields().size()) {
+      return Result.DATA_CONVERSION_NEEDED;
+    }
+
+    for (int i = 0; i < struct.fields().size(); ++i) {
+      if (!struct
+          .fields()
+          .get(i)
+          .name()
+          .equals(tableSchemaType.asStructType().fields().get(i).name())) {
+        return Result.DATA_CONVERSION_NEEDED;
+      }
+    }
+
+    return result;
+  }
+
+  @Override
+  public Result field(Types.NestedField field, Integer tableSchemaId, Result typeResult) {
+    if (tableSchemaId == null) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    if (typeResult != Result.SAME) {
+      return typeResult;
+    }
+
+    if (tableSchema.findField(tableSchemaId).isRequired() && field.isOptional()) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    } else {
+      return Result.SAME;
+    }
+  }
+
+  @Override
+  public Result list(Types.ListType list, Integer tableSchemaId, Result elementsResult) {
+    if (tableSchemaId == null) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    return elementsResult;
+  }
+
+  @Override
+  public Result map(
+      Types.MapType map, Integer tableSchemaId, Result keyResult, Result valueResult) {
+    if (tableSchemaId == null) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    return keyResult.merge(valueResult);
+  }
+
+  @Override
+  @SuppressWarnings("checkstyle:CyclomaticComplexity")
+  public Result primitive(Type.PrimitiveType primitive, Integer tableSchemaId) {
+    if (tableSchemaId == null) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    Type tableSchemaType = tableSchema.findField(tableSchemaId).type();
+    if (!tableSchemaType.isPrimitiveType()) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    Type.PrimitiveType tableSchemaPrimitiveType = tableSchemaType.asPrimitiveType();
+    if (primitive.equals(tableSchemaPrimitiveType)) {
+      return Result.SAME;
+    } else if (primitive.equals(Types.IntegerType.get())
+        && tableSchemaPrimitiveType.equals(Types.LongType.get())) {
+      return Result.DATA_CONVERSION_NEEDED;
+    } else if (primitive.equals(Types.FloatType.get())
+        && tableSchemaPrimitiveType.equals(Types.DoubleType.get())) {
+      return Result.DATA_CONVERSION_NEEDED;
+    } else if (primitive.equals(Types.DateType.get())
+        && tableSchemaPrimitiveType.equals(Types.TimestampType.withoutZone())) {
+      return Result.DATA_CONVERSION_NEEDED;
+    } else if (primitive.typeId() == Type.TypeID.DECIMAL
+        && tableSchemaPrimitiveType.typeId() == Type.TypeID.DECIMAL) {
+      Types.DecimalType dataType = (Types.DecimalType) primitive;
+      Types.DecimalType tableType = (Types.DecimalType) tableSchemaPrimitiveType;
+      return dataType.scale() == tableType.scale() && dataType.precision() < tableType.precision()
+          ? Result.DATA_CONVERSION_NEEDED
+          : Result.SCHEMA_UPDATE_NEEDED;
+    } else {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+  }
+
+  static class PartnerIdByNameAccessors implements PartnerAccessors<Integer> {
+    private final Schema tableSchema;
+    private boolean caseSensitive = true;
+
+    PartnerIdByNameAccessors(Schema tableSchema) {
+      this.tableSchema = tableSchema;
+    }
+
+    private PartnerIdByNameAccessors(Schema tableSchema, boolean caseSensitive) {
+      this(tableSchema);
+      this.caseSensitive = caseSensitive;
+    }
+
+    @Override
+    public Integer fieldPartner(Integer tableSchemaFieldId, int fieldId, String name) {
+      Types.StructType struct;
+      if (tableSchemaFieldId == -1) {
+        struct = tableSchema.asStruct();
+      } else {
+        struct = tableSchema.findField(tableSchemaFieldId).type().asStructType();
+      }
+
+      Types.NestedField field =
+          caseSensitive ? struct.field(name) : struct.caseInsensitiveField(name);
+      if (field != null) {
+        return field.fieldId();
+      }
+
+      return null;
+    }
+
+    @Override
+    public Integer mapKeyPartner(Integer tableSchemaMapId) {
+      Types.NestedField mapField = tableSchema.findField(tableSchemaMapId);
+      if (mapField != null) {
+        return mapField.type().asMapType().fields().get(0).fieldId();
+      }
+
+      return null;
+    }
+
+    @Override
+    public Integer mapValuePartner(Integer tableSchemaMapId) {
+      Types.NestedField mapField = tableSchema.findField(tableSchemaMapId);
+      if (mapField != null) {
+        return mapField.type().asMapType().fields().get(1).fieldId();
+      }
+
+      return null;
+    }
+
+    @Override
+    public Integer listElementPartner(Integer tableSchemaListId) {
+      Types.NestedField listField = tableSchema.findField(tableSchemaListId);
+      if (listField != null) {
+        return listField.type().asListType().fields().get(0).fieldId();
+      }
+
+      return null;
+    }
+  }
+
+  public enum Result {
+    SAME(0),
+    DATA_CONVERSION_NEEDED(1),
+    SCHEMA_UPDATE_NEEDED(2);
+
+    private static final Map<Integer, Result> BY_ID = Maps.newHashMap();
+
+    static {
+      for (Result e : Result.values()) {
+        if (BY_ID.put(e.id, e) != null) {
+          throw new IllegalArgumentException("Duplicate id: " + e.id);
+        }
+      }
+    }
+
+    private final int id;
+
+    Result(int id) {
+      this.id = id;
+    }
+
+    private Result merge(Result other) {
+      return BY_ID.get(Math.max(this.id, other.id));
+    }
+  }
+}
diff --git a/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/EvolveSchemaVisitor.java b/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/EvolveSchemaVisitor.java
new file mode 100644
index 000000000000..85fd5753919e
--- /dev/null
+++ b/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/EvolveSchemaVisitor.java
@@ -0,0 +1,204 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import java.util.List;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.UpdateSchema;
+import org.apache.iceberg.relocated.com.google.common.base.Preconditions;
+import org.apache.iceberg.schema.SchemaWithPartnerVisitor;
+import org.apache.iceberg.types.Type;
+import org.apache.iceberg.types.Types;
+
+/**
+ * Visitor class that accumulates the set of changes needed to evolve an existing schema into the
+ * target schema. Changes are applied to an {@link UpdateSchema} operation.
+ *
+ * <p>We support:
+ *
+ * <ul>
+ *   <li>Adding new columns
+ *   <li>Widening the type of existing columsn
+ *   <li>Reordering columns
+ * </ul>
+ *
+ * We don't support:
+ *
+ * <ul>
+ *   <li>Dropping columns
+ *   <li>Renaming columns
+ * </ul>
+ *
+ * The reason is that dropping columns would create issues with late / out of order data. Once we
+ * drop fields, we wouldn't be able to easily add them back later without losing the associated
+ * data. Renaming columns is not supported because we compare schemas by name, which doesn't allow
+ * for renaming without additional hints.
+ */
+public class EvolveSchemaVisitor extends SchemaWithPartnerVisitor<Integer, Boolean> {
+
+  private final UpdateSchema api;
+  private final Schema existingSchema;
+  private final Schema targetSchema;
+
+  private EvolveSchemaVisitor(UpdateSchema api, Schema existingSchema, Schema targetSchema) {
+    this.api = api;
+    this.existingSchema = existingSchema;
+    this.targetSchema = targetSchema;
+  }
+
+  /**
+   * Adds changes needed to produce the target schema to an {@link UpdateSchema} operation.
+   *
+   * <p>Changes are accumulated to evolve the existingSchema into a targetSchema.
+   *
+   * @param api an UpdateSchema for adding changes
+   * @param existingSchema an existing schema
+   * @param targetSchema a new schema to compare with the existing
+   */
+  public static void visit(UpdateSchema api, Schema existingSchema, Schema targetSchema) {
+    visit(
+        targetSchema,
+        -1,
+        new EvolveSchemaVisitor(api, existingSchema, targetSchema),
+        new CompareSchemasVisitor.PartnerIdByNameAccessors(existingSchema));
+  }
+
+  @Override
+  public Boolean struct(Types.StructType struct, Integer partnerId, List<Boolean> existingFields) {
+    if (partnerId == null) {
+      return true;
+    }
+
+    // Add, update and order fields in the struct
+    Types.StructType partnerStruct = findFieldType(partnerId).asStructType();
+    String after = null;
+    for (Types.NestedField targetField : struct.fields()) {
+      Types.NestedField nestedField = partnerStruct.field(targetField.name());
+      final String columnName;
+      if (nestedField != null) {
+        updateColumn(nestedField, targetField);
+        columnName = this.existingSchema.findColumnName(nestedField.fieldId());
+      } else {
+        addColumn(partnerId, targetField);
+        columnName = this.targetSchema.findColumnName(targetField.fieldId());
+      }
+
+      setPosition(columnName, after);
+      after = columnName;
+    }
+
+    // Ensure that unused fields are made optional
+    for (Types.NestedField existingField : partnerStruct.fields()) {
+      if (struct.field(existingField.name()) == null) {
+        if (existingField.isRequired()) {
+          this.api.makeColumnOptional(this.existingSchema.findColumnName(existingField.fieldId()));
+        }
+      }
+    }
+
+    return false;
+  }
+
+  @Override
+  public Boolean field(Types.NestedField field, Integer partnerId, Boolean isFieldMissing) {
+    return partnerId == null;
+  }
+
+  @Override
+  public Boolean list(Types.ListType list, Integer partnerId, Boolean isElementMissing) {
+    if (partnerId == null) {
+      return true;
+    }
+
+    Preconditions.checkState(
+        !isElementMissing, "Error traversing schemas: element is missing, but list is present");
+
+    Types.ListType partnerList = findFieldType(partnerId).asListType();
+    updateColumn(partnerList.fields().get(0), list.fields().get(0));
+
+    return false;
+  }
+
+  @Override
+  public Boolean map(
+      Types.MapType map, Integer partnerId, Boolean isKeyMissing, Boolean isValueMissing) {
+    if (partnerId == null) {
+      return true;
+    }
+
+    Preconditions.checkState(
+        !isKeyMissing, "Error traversing schemas: key is missing, but map is present");
+    Preconditions.checkState(
+        !isValueMissing, "Error traversing schemas: value is missing, but map is present");
+
+    Types.MapType partnerMap = findFieldType(partnerId).asMapType();
+    updateColumn(partnerMap.fields().get(0), map.fields().get(0));
+    updateColumn(partnerMap.fields().get(1), map.fields().get(1));
+
+    return false;
+  }
+
+  @Override
+  public Boolean primitive(Type.PrimitiveType primitive, Integer partnerId) {
+    return partnerId == null;
+  }
+
+  private Type findFieldType(int fieldId) {
+    if (fieldId == -1) {
+      return existingSchema.asStruct();
+    } else {
+      return existingSchema.findField(fieldId).type();
+    }
+  }
+
+  private void addColumn(int parentId, Types.NestedField field) {
+    String parentName = targetSchema.findColumnName(parentId);
+    api.addColumn(parentName, field.name(), field.type(), field.doc());
+  }
+
+  private void updateColumn(Types.NestedField existingField, Types.NestedField targetField) {
+    String existingColumnName = this.existingSchema.findColumnName(existingField.fieldId());
+
+    boolean needsOptionalUpdate = targetField.isOptional() && existingField.isRequired();
+    boolean needsTypeUpdate =
+        targetField.type().isPrimitiveType() && !targetField.type().equals(existingField.type());
+    boolean needsDocUpdate =
+        targetField.doc() != null && !targetField.doc().equals(existingField.doc());
+
+    if (needsOptionalUpdate) {
+      api.makeColumnOptional(existingColumnName);
+    }
+
+    if (needsTypeUpdate) {
+      api.updateColumn(existingColumnName, targetField.type().asPrimitiveType());
+    }
+
+    if (needsDocUpdate) {
+      api.updateColumnDoc(existingColumnName, targetField.doc());
+    }
+  }
+
+  private void setPosition(String columnName, String after) {
+    if (after == null) {
+      this.api.moveFirst(columnName);
+    } else {
+      this.api.moveAfter(columnName, after);
+    }
+  }
+}
diff --git a/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/PartitionSpecEvolution.java b/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/PartitionSpecEvolution.java
new file mode 100644
index 000000000000..90b6c7295cb7
--- /dev/null
+++ b/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/PartitionSpecEvolution.java
@@ -0,0 +1,137 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import java.util.List;
+import org.apache.iceberg.PartitionField;
+import org.apache.iceberg.PartitionSpec;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.expressions.Expressions;
+import org.apache.iceberg.expressions.Term;
+import org.apache.iceberg.relocated.com.google.common.base.MoreObjects;
+import org.apache.iceberg.relocated.com.google.common.collect.Iterables;
+import org.apache.iceberg.relocated.com.google.common.collect.Lists;
+
+/** Checks compatibility of PartitionSpecs and evolves one into the other. */
+public class PartitionSpecEvolution {
+
+  private PartitionSpecEvolution() {}
+
+  /**
+   * Checks whether two PartitionSpecs are compatible with each other. Less strict than {@code
+   * PartitionSpec#compatible} in the sense that it tolerates differently named partition fields, as
+   * long as their transforms and field names corresponding to their source ids match.
+   */
+  public static boolean checkCompatibility(PartitionSpec spec1, PartitionSpec spec2) {
+    if (spec1.equals(spec2)) {
+      return true;
+    }
+
+    if (spec1.fields().size() != spec2.fields().size()) {
+      return false;
+    }
+
+    for (int i = 0; i < spec1.fields().size(); i++) {
+      PartitionField field1 = spec1.fields().get(i);
+      PartitionField field2 = spec2.fields().get(i);
+      if (!specFieldsAreCompatible(field1, spec1.schema(), field2, spec2.schema())) {
+        return false;
+      }
+    }
+
+    return true;
+  }
+
+  static PartitionSpecChanges evolve(PartitionSpec currentSpec, PartitionSpec targetSpec) {
+    if (currentSpec.compatibleWith(targetSpec)) {
+      return new PartitionSpecChanges();
+    }
+
+    PartitionSpecChanges result = new PartitionSpecChanges();
+
+    int maxNumFields = Math.max(currentSpec.fields().size(), targetSpec.fields().size());
+    for (int i = 0; i < maxNumFields; i++) {
+      PartitionField currentField = Iterables.get(currentSpec.fields(), i, null);
+      PartitionField targetField = Iterables.get(targetSpec.fields(), i, null);
+
+      if (!specFieldsAreCompatible(
+          currentField, currentSpec.schema(), targetField, targetSpec.schema())) {
+
+        if (currentField != null) {
+          result.remove(toTerm(currentField, currentSpec.schema()));
+        }
+
+        if (targetField != null) {
+          result.add(toTerm(targetField, targetSpec.schema()));
+        }
+      }
+    }
+
+    return result;
+  }
+
+  static class PartitionSpecChanges {
+    private final List<Term> termsToAdd = Lists.newArrayList();
+    private final List<Term> termsToRemove = Lists.newArrayList();
+
+    public void add(Term term) {
+      termsToAdd.add(term);
+    }
+
+    public void remove(Term term) {
+      termsToRemove.add(term);
+    }
+
+    public List<Term> termsToAdd() {
+      return termsToAdd;
+    }
+
+    public List<Term> termsToRemove() {
+      return termsToRemove;
+    }
+
+    public boolean isEmpty() {
+      return termsToAdd.isEmpty() && termsToRemove.isEmpty();
+    }
+
+    @Override
+    public String toString() {
+      return MoreObjects.toStringHelper(PartitionSpecEvolution.class)
+          .add("termsToAdd", termsToAdd)
+          .add("termsToRemove", termsToRemove)
+          .toString();
+    }
+  }
+
+  private static Term toTerm(PartitionField field, Schema schema) {
+    String sourceName = schema.idToName().get(field.sourceId());
+    return Expressions.transform(sourceName, field.transform());
+  }
+
+  private static boolean specFieldsAreCompatible(
+      PartitionField field1, Schema schemaField1, PartitionField field2, Schema schemaField2) {
+    if (field1 == null || field2 == null) {
+      return false;
+    }
+    String firstFieldSourceName = schemaField1.idToName().get(field1.sourceId());
+    String secondFieldSourceName = schemaField2.idToName().get(field2.sourceId());
+    return firstFieldSourceName.equals(secondFieldSourceName)
+        && field1.transform().toString().equals(field2.transform().toString());
+  }
+}
diff --git a/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/TableMetadataCache.java b/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/TableMetadataCache.java
new file mode 100644
index 000000000000..e9c77ea8c809
--- /dev/null
+++ b/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/TableMetadataCache.java
@@ -0,0 +1,261 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import com.github.benmanes.caffeine.cache.Cache;
+import com.github.benmanes.caffeine.cache.Caffeine;
+import java.util.LinkedHashMap;
+import java.util.Map;
+import java.util.Set;
+import org.apache.flink.annotation.Internal;
+import org.apache.flink.annotation.VisibleForTesting;
+import org.apache.flink.api.java.tuple.Tuple2;
+import org.apache.iceberg.PartitionSpec;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.Table;
+import org.apache.iceberg.catalog.Catalog;
+import org.apache.iceberg.catalog.TableIdentifier;
+import org.apache.iceberg.exceptions.NoSuchTableException;
+import org.slf4j.Logger;
+import org.slf4j.LoggerFactory;
+
+/**
+ * TableMetadataCache is responsible for caching table metadata to avoid hitting the catalog too
+ * frequently. We store table identifier, schema, partition spec, and a set of past schema
+ * comparison results of the active table schema against the last input schemas.
+ */
+@Internal
+class TableMetadataCache {
+
+  private static final Logger LOG = LoggerFactory.getLogger(TableMetadataCache.class);
+  private static final int MAX_SCHEMA_COMPARISON_RESULTS_TO_CACHE = 10;
+  private static final Tuple2<Boolean, Exception> EXISTS = Tuple2.of(true, null);
+  private static final Tuple2<Boolean, Exception> NOT_EXISTS = Tuple2.of(false, null);
+  static final Tuple2<Schema, CompareSchemasVisitor.Result> NOT_FOUND =
+      Tuple2.of(null, CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+
+  private final Catalog catalog;
+  private final long refreshMs;
+  private final Cache<TableIdentifier, CacheItem> cache;
+
+  TableMetadataCache(Catalog catalog, int maximumSize, long refreshMs) {
+    this.catalog = catalog;
+    this.refreshMs = refreshMs;
+    this.cache = Caffeine.newBuilder().maximumSize(maximumSize).build();
+  }
+
+  Tuple2<Boolean, Exception> exists(TableIdentifier identifier) {
+    CacheItem cached = cache.getIfPresent(identifier);
+    if (cached != null && Boolean.TRUE.equals(cached.tableExists)) {
+      return EXISTS;
+    } else if (needsRefresh(cached, true)) {
+      return refreshTable(identifier);
+    } else {
+      return NOT_EXISTS;
+    }
+  }
+
+  String branch(TableIdentifier identifier, String branch) {
+    return branch(identifier, branch, true);
+  }
+
+  Tuple2<Schema, CompareSchemasVisitor.Result> schema(TableIdentifier identifier, Schema input) {
+    return schema(identifier, input, true);
+  }
+
+  PartitionSpec spec(TableIdentifier identifier, PartitionSpec spec) {
+    return spec(identifier, spec, true);
+  }
+
+  void update(TableIdentifier identifier, Table table) {
+    cache.put(
+        identifier,
+        new CacheItem(true, table.refs().keySet(), new SchemaInfo(table.schemas()), table.specs()));
+  }
+
+  private String branch(TableIdentifier identifier, String branch, boolean allowRefresh) {
+    CacheItem cached = cache.getIfPresent(identifier);
+    if (cached != null && cached.tableExists && cached.branches.contains(branch)) {
+      return branch;
+    }
+
+    if (needsRefresh(cached, allowRefresh)) {
+      refreshTable(identifier);
+      return branch(identifier, branch, false);
+    } else {
+      return null;
+    }
+  }
+
+  private Tuple2<Schema, CompareSchemasVisitor.Result> schema(
+      TableIdentifier identifier, Schema input, boolean allowRefresh) {
+    CacheItem cached = cache.getIfPresent(identifier);
+    Schema compatible = null;
+    if (cached != null && cached.tableExists) {
+      // This only works if the {@link Schema#equals(Object)} returns true for the old schema
+      // and a new schema. Performance is paramount as this code is on the hot path. Every other
+      // way for comparing 2 schemas were performing worse than the
+      // {@link CompareByNameVisitor#visit(Schema, Schema, boolean)}, so caching was useless.
+      Tuple2<Schema, CompareSchemasVisitor.Result> lastResult =
+          cached.schema.lastResults.get(input);
+      if (lastResult != null) {
+        return lastResult;
+      }
+
+      for (Map.Entry<Integer, Schema> tableSchema : cached.schema.schemas.entrySet()) {
+        CompareSchemasVisitor.Result result =
+            CompareSchemasVisitor.visit(input, tableSchema.getValue(), true);
+        if (result == CompareSchemasVisitor.Result.SAME) {
+          Tuple2<Schema, CompareSchemasVisitor.Result> newResult =
+              Tuple2.of(tableSchema.getValue(), CompareSchemasVisitor.Result.SAME);
+          cached.schema.update(input, newResult);
+          return newResult;
+        } else if (compatible == null
+            && result == CompareSchemasVisitor.Result.DATA_CONVERSION_NEEDED) {
+          compatible = tableSchema.getValue();
+        }
+      }
+    }
+
+    if (needsRefresh(cached, allowRefresh)) {
+      refreshTable(identifier);
+      return schema(identifier, input, false);
+    } else if (compatible != null) {
+      Tuple2<Schema, CompareSchemasVisitor.Result> newResult =
+          Tuple2.of(compatible, CompareSchemasVisitor.Result.DATA_CONVERSION_NEEDED);
+      cached.schema.update(input, newResult);
+      return newResult;
+    } else if (cached != null && cached.tableExists) {
+      cached.schema.update(input, NOT_FOUND);
+      return NOT_FOUND;
+    } else {
+      return NOT_FOUND;
+    }
+  }
+
+  private PartitionSpec spec(TableIdentifier identifier, PartitionSpec spec, boolean allowRefresh) {
+    CacheItem cached = cache.getIfPresent(identifier);
+    if (cached != null && cached.tableExists) {
+      for (PartitionSpec tableSpec : cached.specs.values()) {
+        if (PartitionSpecEvolution.checkCompatibility(tableSpec, spec)) {
+          return tableSpec;
+        }
+      }
+    }
+
+    if (needsRefresh(cached, allowRefresh)) {
+      refreshTable(identifier);
+      return spec(identifier, spec, false);
+    } else {
+      return null;
+    }
+  }
+
+  private Tuple2<Boolean, Exception> refreshTable(TableIdentifier identifier) {
+    try {
+      Table table = catalog.loadTable(identifier);
+      update(identifier, table);
+      return EXISTS;
+    } catch (NoSuchTableException e) {
+      LOG.debug("Table doesn't exist {}", identifier, e);
+      cache.put(identifier, new CacheItem(false, null, null, null));
+      return Tuple2.of(false, e);
+    }
+  }
+
+  private boolean needsRefresh(CacheItem cacheItem, boolean allowRefresh) {
+    return allowRefresh
+        && (cacheItem == null || cacheItem.created + refreshMs > System.currentTimeMillis());
+  }
+
+  public void invalidate(TableIdentifier identifier) {
+    cache.invalidate(identifier);
+  }
+
+  /** Handles timeout for missing items only. Caffeine performance causes noticeable delays. */
+  static class CacheItem {
+    private final long created = System.currentTimeMillis();
+
+    private final boolean tableExists;
+    private final Set<String> branches;
+    private final SchemaInfo schema;
+    private final Map<Integer, PartitionSpec> specs;
+
+    private CacheItem(
+        boolean tableExists,
+        Set<String> branches,
+        SchemaInfo schema,
+        Map<Integer, PartitionSpec> specs) {
+      this.tableExists = tableExists;
+      this.branches = branches;
+      this.schema = schema;
+      this.specs = specs;
+    }
+
+    @VisibleForTesting
+    SchemaInfo getSchemaInfo() {
+      return schema;
+    }
+  }
+
+  /**
+   * Stores precalculated results for {@link CompareSchemasVisitor#visit(Schema, Schema, boolean)}
+   * in the cache.
+   */
+  static class SchemaInfo {
+    private final Map<Integer, Schema> schemas;
+    private final Map<Schema, Tuple2<Schema, CompareSchemasVisitor.Result>> lastResults;
+
+    private SchemaInfo(Map<Integer, Schema> schemas) {
+      this.schemas = schemas;
+      this.lastResults = new LimitedLinkedHashMap<>();
+    }
+
+    private void update(
+        Schema newLastSchema, Tuple2<Schema, CompareSchemasVisitor.Result> newLastResult) {
+      lastResults.put(newLastSchema, newLastResult);
+    }
+
+    @VisibleForTesting
+    Tuple2<Schema, CompareSchemasVisitor.Result> getLastResult(Schema schema) {
+      return lastResults.get(schema);
+    }
+  }
+
+  @SuppressWarnings("checkstyle:IllegalType")
+  private static class LimitedLinkedHashMap<K, V> extends LinkedHashMap<K, V> {
+    @Override
+    protected boolean removeEldestEntry(Map.Entry<K, V> eldest) {
+      boolean remove = size() > MAX_SCHEMA_COMPARISON_RESULTS_TO_CACHE;
+      if (remove) {
+        LOG.warn(
+            "Performance degraded as records with different schema is generated for the same table. "
+                + "Likely the DynamicRecord.schema is not reused. "
+                + "Reuse the same instance if the record schema is the same to improve performance");
+      }
+
+      return remove;
+    }
+  }
+
+  @VisibleForTesting
+  Cache<TableIdentifier, CacheItem> getInternalCache() {
+    return cache;
+  }
+}
diff --git a/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/TableUpdater.java b/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/TableUpdater.java
new file mode 100644
index 000000000000..40bb66f65125
--- /dev/null
+++ b/flink/v1.19/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/TableUpdater.java
@@ -0,0 +1,207 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import org.apache.flink.annotation.Internal;
+import org.apache.flink.api.java.tuple.Tuple2;
+import org.apache.flink.api.java.tuple.Tuple3;
+import org.apache.iceberg.PartitionSpec;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.Table;
+import org.apache.iceberg.UpdatePartitionSpec;
+import org.apache.iceberg.UpdateSchema;
+import org.apache.iceberg.catalog.Catalog;
+import org.apache.iceberg.catalog.SupportsNamespaces;
+import org.apache.iceberg.catalog.TableIdentifier;
+import org.apache.iceberg.exceptions.AlreadyExistsException;
+import org.apache.iceberg.exceptions.CommitFailedException;
+import org.apache.iceberg.exceptions.NoSuchNamespaceException;
+import org.slf4j.Logger;
+import org.slf4j.LoggerFactory;
+
+/** Updates the Iceberg tables in case of schema, branch, or partition changes. */
+@Internal
+class TableUpdater {
+
+  private static final Logger LOG = LoggerFactory.getLogger(TableUpdater.class);
+  private final TableMetadataCache cache;
+  private final Catalog catalog;
+
+  TableUpdater(TableMetadataCache cache, Catalog catalog) {
+    this.cache = cache;
+    this.catalog = catalog;
+  }
+
+  /**
+   * Creates or updates a table to make sure that the given branch, schema, spec exists.
+   *
+   * @return a {@link Tuple3} of the new {@link Schema}, the status of the schema compared to the
+   *     requested one, and the new {@link PartitionSpec#specId()}.
+   */
+  Tuple3<Schema, CompareSchemasVisitor.Result, PartitionSpec> update(
+      TableIdentifier tableIdentifier, String branch, Schema schema, PartitionSpec spec) {
+    findOrCreateTable(tableIdentifier, schema, spec);
+    findOrCreateBranch(tableIdentifier, branch);
+    Tuple2<Schema, CompareSchemasVisitor.Result> newSchema =
+        findOrCreateSchema(tableIdentifier, schema);
+    PartitionSpec newSpec = findOrCreateSpec(tableIdentifier, spec);
+    return Tuple3.of(newSchema.f0, newSchema.f1, newSpec);
+  }
+
+  private void findOrCreateTable(TableIdentifier identifier, Schema schema, PartitionSpec spec) {
+    Tuple2<Boolean, Exception> exists = cache.exists(identifier);
+    if (Boolean.FALSE.equals(exists.f0)) {
+      if (exists.f1 instanceof NoSuchNamespaceException) {
+        SupportsNamespaces catalogWithNameSpace = (SupportsNamespaces) catalog;
+        LOG.info("Namespace {} not found during table search. Creating namespace", identifier);
+        try {
+          catalogWithNameSpace.createNamespace(identifier.namespace());
+        } catch (AlreadyExistsException e) {
+          LOG.debug("Namespace {} created concurrently", identifier.namespace(), e);
+        }
+      }
+
+      LOG.info("Table {} not found during table search. Creating table.", identifier);
+      try {
+        Table table = catalog.createTable(identifier, schema, spec);
+        cache.update(identifier, table);
+      } catch (AlreadyExistsException e) {
+        LOG.debug("Table {} created concurrently. Skipping creation.", identifier, e);
+        cache.invalidate(identifier);
+        findOrCreateTable(identifier, schema, spec);
+      }
+    }
+  }
+
+  private void findOrCreateBranch(TableIdentifier identifier, String branch) {
+    String fromCache = cache.branch(identifier, branch);
+    if (fromCache == null) {
+      Table table = catalog.loadTable(identifier);
+      try {
+        table.manageSnapshots().createBranch(branch).commit();
+        LOG.info("Branch {} for {} created", branch, identifier);
+      } catch (CommitFailedException e) {
+        table.refresh();
+        if (table.refs().containsKey(branch)) {
+          LOG.debug("Branch {} concurrently created for {}.", branch, identifier);
+        } else {
+          LOG.error("Failed to create branch {} for {}.", branch, identifier, e);
+          throw e;
+        }
+      }
+
+      cache.update(identifier, table);
+    }
+  }
+
+  private Tuple2<Schema, CompareSchemasVisitor.Result> findOrCreateSchema(
+      TableIdentifier identifier, Schema schema) {
+    Tuple2<Schema, CompareSchemasVisitor.Result> fromCache = cache.schema(identifier, schema);
+    if (fromCache.f1 != CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED) {
+      return fromCache;
+    } else {
+      Table table = catalog.loadTable(identifier);
+      Schema tableSchema = table.schema();
+      CompareSchemasVisitor.Result result = CompareSchemasVisitor.visit(schema, tableSchema, true);
+      switch (result) {
+        case SAME:
+        case DATA_CONVERSION_NEEDED:
+          cache.update(identifier, table);
+          return Tuple2.of(tableSchema, result);
+        case SCHEMA_UPDATE_NEEDED:
+          LOG.info(
+              "Triggering schema update for table {} {} to {}", identifier, tableSchema, schema);
+          UpdateSchema updateApi = table.updateSchema();
+          EvolveSchemaVisitor.visit(updateApi, tableSchema, schema);
+
+          try {
+            updateApi.commit();
+            cache.update(identifier, table);
+            Tuple2<Schema, CompareSchemasVisitor.Result> comparisonAfterMigration =
+                cache.schema(identifier, schema);
+            Schema newSchema = comparisonAfterMigration.f0;
+            LOG.info("Table {} schema updated from {} to {}", identifier, tableSchema, newSchema);
+            return comparisonAfterMigration;
+          } catch (CommitFailedException e) {
+            cache.invalidate(identifier);
+            Tuple2<Schema, CompareSchemasVisitor.Result> newSchema =
+                cache.schema(identifier, schema);
+            if (newSchema.f1 != CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED) {
+              LOG.debug("Table {} schema updated concurrently to {}", identifier, schema);
+              return newSchema;
+            } else {
+              LOG.error(
+                  "Schema update failed for {} from {} to {}", identifier, tableSchema, schema, e);
+              throw e;
+            }
+          }
+        default:
+          throw new IllegalArgumentException("Unknown comparison result");
+      }
+    }
+  }
+
+  private PartitionSpec findOrCreateSpec(TableIdentifier identifier, PartitionSpec targetSpec) {
+    PartitionSpec currentSpec = cache.spec(identifier, targetSpec);
+    if (currentSpec != null) {
+      return currentSpec;
+    }
+
+    Table table = catalog.loadTable(identifier);
+    currentSpec = table.spec();
+
+    PartitionSpecEvolution.PartitionSpecChanges result =
+        PartitionSpecEvolution.evolve(currentSpec, targetSpec);
+    if (result.isEmpty()) {
+      LOG.info("Returning equivalent existing spec {} for {}", currentSpec, targetSpec);
+      return currentSpec;
+    }
+
+    LOG.info(
+        "Spec for table {} has been altered. Updating from {} to {}",
+        identifier,
+        currentSpec,
+        targetSpec);
+    UpdatePartitionSpec updater = table.updateSpec();
+    result.termsToRemove().forEach(updater::removeField);
+    result.termsToAdd().forEach(updater::addField);
+
+    try {
+      updater.commit();
+      cache.update(identifier, table);
+    } catch (CommitFailedException e) {
+      cache.invalidate(identifier);
+      PartitionSpec newSpec = cache.spec(identifier, targetSpec);
+      result = PartitionSpecEvolution.evolve(targetSpec, newSpec);
+      if (result.isEmpty()) {
+        LOG.debug("Table {} partition spec updated concurrently to {}", identifier, newSpec);
+        return newSpec;
+      } else {
+        LOG.error(
+            "Partition spec update failed for {} from {} to {}",
+            identifier,
+            currentSpec,
+            targetSpec,
+            e);
+        throw e;
+      }
+    }
+    return cache.spec(identifier, targetSpec);
+  }
+}
diff --git a/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestCompareSchemasVisitor.java b/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestCompareSchemasVisitor.java
new file mode 100644
index 000000000000..487b0ee7d94a
--- /dev/null
+++ b/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestCompareSchemasVisitor.java
@@ -0,0 +1,209 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import static org.apache.iceberg.types.Types.NestedField.optional;
+import static org.apache.iceberg.types.Types.NestedField.required;
+import static org.assertj.core.api.Assertions.assertThat;
+
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.types.Types.IntegerType;
+import org.apache.iceberg.types.Types.ListType;
+import org.apache.iceberg.types.Types.LongType;
+import org.apache.iceberg.types.Types.MapType;
+import org.apache.iceberg.types.Types.StringType;
+import org.apache.iceberg.types.Types.StructType;
+import org.junit.jupiter.api.Test;
+
+class TestCompareSchemasVisitor {
+
+  @Test
+  void testSchema() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", IntegerType.get(), "comment"),
+                    optional(2, "data", StringType.get()),
+                    optional(3, "extra", StringType.get())),
+                new Schema(
+                    optional(1, "id", IntegerType.get(), "comment"),
+                    optional(2, "data", StringType.get()),
+                    optional(3, "extra", StringType.get()))))
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+  }
+
+  @Test
+  void testSchemaDifferentId() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(1, "data", StringType.get()),
+                    optional(2, "extra", StringType.get())),
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(2, "data", StringType.get()),
+                    optional(3, "extra", StringType.get()))))
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+  }
+
+  @Test
+  void testSchemaDifferent() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(1, "data", StringType.get()),
+                    optional(2, "extra", StringType.get())),
+                new Schema(
+                    optional(0, "id", IntegerType.get()), optional(1, "data", StringType.get()))))
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+  }
+
+  @Test
+  void testSchemaWithMoreColumns() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(0, "id", IntegerType.get()), optional(1, "data", StringType.get())),
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(1, "data", StringType.get()),
+                    optional(2, "extra", StringType.get()))))
+        .isEqualTo(CompareSchemasVisitor.Result.DATA_CONVERSION_NEEDED);
+  }
+
+  @Test
+  void testDifferentType() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", LongType.get()), optional(2, "extra", StringType.get())),
+                new Schema(
+                    optional(1, "id", IntegerType.get()), optional(2, "extra", StringType.get()))))
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+  }
+
+  @Test
+  void testCompatibleType() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", IntegerType.get()), optional(2, "extra", StringType.get())),
+                new Schema(
+                    optional(1, "id", LongType.get()), optional(2, "extra", StringType.get()))))
+        .isEqualTo(CompareSchemasVisitor.Result.DATA_CONVERSION_NEEDED);
+  }
+
+  @Test
+  void testWithRequiredChange() {
+    Schema dataSchema =
+        new Schema(optional(1, "id", IntegerType.get()), optional(2, "extra", StringType.get()));
+    Schema tableSchema =
+        new Schema(required(1, "id", IntegerType.get()), optional(2, "extra", StringType.get()));
+    assertThat(CompareSchemasVisitor.visit(dataSchema, tableSchema))
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+    assertThat(CompareSchemasVisitor.visit(tableSchema, dataSchema))
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+  }
+
+  @Test
+  void testStructDifferentId() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(2, "struct1", StructType.of(optional(3, "extra", IntegerType.get())))),
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(
+                        1, "struct1", StructType.of(optional(2, "extra", IntegerType.get()))))))
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+  }
+
+  @Test
+  void testStructChanged() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(1, "struct1", StructType.of(optional(2, "extra", LongType.get())))),
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(
+                        2, "struct1", StructType.of(optional(3, "extra", IntegerType.get()))))))
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+  }
+
+  @Test
+  void testMapDifferentId() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(
+                        2, "map1", MapType.ofOptional(3, 4, IntegerType.get(), StringType.get()))),
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(
+                        1, "map1", MapType.ofOptional(2, 3, IntegerType.get(), StringType.get())))))
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+  }
+
+  @Test
+  void testMapChanged() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(
+                        2, "map1", MapType.ofOptional(3, 4, LongType.get(), StringType.get()))),
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(
+                        2, "map1", MapType.ofOptional(3, 4, IntegerType.get(), StringType.get())))))
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+  }
+
+  @Test
+  void testListDifferentId() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(2, "list1", ListType.ofOptional(3, IntegerType.get()))),
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(1, "list1", ListType.ofOptional(2, IntegerType.get())))))
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+  }
+
+  @Test
+  void testListChanged() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(1, "list1", ListType.ofOptional(2, LongType.get()))),
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(2, "list1", ListType.ofOptional(3, IntegerType.get())))))
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+  }
+}
diff --git a/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestEvolveSchemaVisitor.java b/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestEvolveSchemaVisitor.java
new file mode 100644
index 000000000000..58ee84529193
--- /dev/null
+++ b/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestEvolveSchemaVisitor.java
@@ -0,0 +1,623 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import static org.apache.iceberg.types.Types.NestedField.of;
+import static org.apache.iceberg.types.Types.NestedField.optional;
+import static org.apache.iceberg.types.Types.NestedField.required;
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.assertThatThrownBy;
+
+import java.lang.reflect.Constructor;
+import java.util.Arrays;
+import java.util.List;
+import java.util.concurrent.atomic.AtomicInteger;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.UpdateSchema;
+import org.apache.iceberg.relocated.com.google.common.collect.Lists;
+import org.apache.iceberg.types.Type.PrimitiveType;
+import org.apache.iceberg.types.Types;
+import org.apache.iceberg.types.Types.DecimalType;
+import org.apache.iceberg.types.Types.DoubleType;
+import org.apache.iceberg.types.Types.FloatType;
+import org.apache.iceberg.types.Types.IntegerType;
+import org.apache.iceberg.types.Types.ListType;
+import org.apache.iceberg.types.Types.LongType;
+import org.apache.iceberg.types.Types.MapType;
+import org.apache.iceberg.types.Types.StringType;
+import org.apache.iceberg.types.Types.StructType;
+import org.apache.iceberg.types.Types.TimeType;
+import org.apache.iceberg.types.Types.UUIDType;
+import org.junit.jupiter.api.Test;
+
+public class TestEvolveSchemaVisitor {
+
+  private static List<? extends PrimitiveType> primitiveTypes() {
+    return Lists.newArrayList(
+        StringType.get(),
+        TimeType.get(),
+        Types.TimestampType.withoutZone(),
+        Types.TimestampType.withZone(),
+        UUIDType.get(),
+        Types.DateType.get(),
+        Types.BooleanType.get(),
+        Types.BinaryType.get(),
+        DoubleType.get(),
+        IntegerType.get(),
+        Types.FixedType.ofLength(10),
+        DecimalType.of(10, 2),
+        LongType.get(),
+        FloatType.get());
+  }
+
+  private static Types.NestedField[] primitiveFields(
+      Integer initialValue, List<? extends PrimitiveType> primitiveTypes) {
+    return primitiveFields(initialValue, primitiveTypes, true);
+  }
+
+  private static Types.NestedField[] primitiveFields(
+      Integer initialValue, List<? extends PrimitiveType> primitiveTypes, boolean optional) {
+    AtomicInteger atomicInteger = new AtomicInteger(initialValue);
+    return primitiveTypes.stream()
+        .map(
+            type ->
+                of(
+                    atomicInteger.incrementAndGet(),
+                    optional,
+                    type.toString(),
+                    Types.fromPrimitiveString(type.toString())))
+        .toArray(Types.NestedField[]::new);
+  }
+
+  @Test
+  public void testAddTopLevelPrimitives() {
+    Schema targetSchema = new Schema(primitiveFields(0, primitiveTypes()));
+    UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+    EvolveSchemaVisitor.visit(updateApi, new Schema(), targetSchema);
+    assertThat(targetSchema.asStruct()).isEqualTo(updateApi.apply().asStruct());
+  }
+
+  @Test
+  public void testMakeTopLevelPrimitivesOptional() {
+    Schema existingSchema = new Schema(primitiveFields(0, primitiveTypes(), false));
+    assertThat(existingSchema.columns().stream().allMatch(Types.NestedField::isRequired)).isTrue();
+
+    UpdateSchema updateApi = loadUpdateApi(existingSchema, 0);
+    EvolveSchemaVisitor.visit(updateApi, existingSchema, new Schema());
+    Schema newSchema = updateApi.apply();
+    assertThat(newSchema.asStruct().fields().size()).isEqualTo(14);
+    assertThat(newSchema.columns().stream().allMatch(Types.NestedField::isOptional)).isTrue();
+  }
+
+  @Test
+  public void testIdentifyFieldsByName() {
+    Schema existingSchema =
+        new Schema(Types.NestedField.optional(42, "myField", Types.LongType.get()));
+    UpdateSchema updateApi = loadUpdateApi(existingSchema, 0);
+    Schema newSchema =
+        new Schema(Arrays.asList(Types.NestedField.optional(-1, "myField", Types.LongType.get())));
+    EvolveSchemaVisitor.visit(updateApi, existingSchema, newSchema);
+    assertThat(updateApi.apply().sameSchema(existingSchema)).isTrue();
+  }
+
+  @Test
+  public void testChangeOrderTopLevelPrimitives() {
+    Schema existingSchema =
+        new Schema(
+            Arrays.asList(optional(1, "a", StringType.get()), optional(2, "b", StringType.get())));
+    Schema targetSchema =
+        new Schema(
+            Arrays.asList(optional(2, "b", StringType.get()), optional(1, "a", StringType.get())));
+    UpdateSchema updateApi = loadUpdateApi(existingSchema, 0);
+    EvolveSchemaVisitor.visit(updateApi, existingSchema, targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testAddTopLevelListOfPrimitives() {
+    for (PrimitiveType primitiveType : primitiveTypes()) {
+      Schema targetSchema = new Schema(optional(1, "aList", ListType.ofOptional(2, primitiveType)));
+      UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+      EvolveSchemaVisitor.visit(updateApi, new Schema(), targetSchema);
+      assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+    }
+  }
+
+  @Test
+  public void testMakeTopLevelListOfPrimitivesOptional() {
+    for (PrimitiveType primitiveType : primitiveTypes()) {
+      Schema existingSchema =
+          new Schema(optional(1, "aList", ListType.ofRequired(2, primitiveType)));
+      Schema targetSchema = new Schema();
+      UpdateSchema updateApi = loadUpdateApi(existingSchema, 0);
+      EvolveSchemaVisitor.visit(updateApi, existingSchema, targetSchema);
+      Schema expectedSchema =
+          new Schema(optional(1, "aList", ListType.ofRequired(2, primitiveType)));
+      assertThat(updateApi.apply().asStruct()).isEqualTo(expectedSchema.asStruct());
+    }
+  }
+
+  @Test
+  public void testAddTopLevelMapOfPrimitives() {
+    for (PrimitiveType primitiveType : primitiveTypes()) {
+      Schema targetSchema =
+          new Schema(optional(1, "aMap", MapType.ofOptional(2, 3, primitiveType, primitiveType)));
+      UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+      EvolveSchemaVisitor.visit(updateApi, new Schema(), targetSchema);
+      assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+    }
+  }
+
+  @Test
+  public void testAddTopLevelStructOfPrimitives() {
+    for (PrimitiveType primitiveType : primitiveTypes()) {
+      Schema currentSchema =
+          new Schema(
+              optional(1, "aStruct", StructType.of(optional(2, "primitive", primitiveType))));
+      UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+      EvolveSchemaVisitor.visit(updateApi, new Schema(), currentSchema);
+      assertThat(updateApi.apply().asStruct()).isEqualTo(currentSchema.asStruct());
+    }
+  }
+
+  @Test
+  public void testAddNestedPrimitive() {
+    for (PrimitiveType primitiveType : primitiveTypes()) {
+      Schema currentSchema = new Schema(optional(1, "aStruct", StructType.of()));
+      Schema targetSchema =
+          new Schema(
+              optional(1, "aStruct", StructType.of(optional(2, "primitive", primitiveType))));
+      UpdateSchema updateApi = loadUpdateApi(currentSchema, 1);
+      EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+      assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+    }
+  }
+
+  @Test
+  public void testMakeNestedPrimitiveOptional() {
+    for (PrimitiveType primitiveType : primitiveTypes()) {
+      Schema currentSchema =
+          new Schema(
+              optional(1, "aStruct", StructType.of(required(2, "primitive", primitiveType))));
+      Schema targetSchema =
+          new Schema(
+              optional(1, "aStruct", StructType.of(optional(2, "primitive", primitiveType))));
+      UpdateSchema updateApi = loadUpdateApi(currentSchema, 1);
+      EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+      assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+    }
+  }
+
+  @Test
+  public void testAddNestedPrimitives() {
+    Schema currentSchema = new Schema(optional(1, "aStruct", StructType.of()));
+    Schema targetSchema =
+        new Schema(optional(1, "aStruct", StructType.of(primitiveFields(1, primitiveTypes()))));
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 1);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testAddNestedLists() {
+    Schema targetSchema =
+        new Schema(
+            optional(
+                1,
+                "aList",
+                ListType.ofOptional(
+                    2,
+                    ListType.ofOptional(
+                        3,
+                        ListType.ofOptional(
+                            4,
+                            ListType.ofOptional(
+                                5,
+                                ListType.ofOptional(
+                                    6,
+                                    ListType.ofOptional(
+                                        7,
+                                        ListType.ofOptional(
+                                            8,
+                                            ListType.ofOptional(
+                                                9,
+                                                ListType.ofOptional(
+                                                    10, DecimalType.of(11, 20))))))))))));
+    UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+    EvolveSchemaVisitor.visit(updateApi, new Schema(), targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testAddNestedStruct() {
+    Schema targetSchema =
+        new Schema(
+            optional(
+                1,
+                "struct1",
+                StructType.of(
+                    optional(
+                        2,
+                        "struct2",
+                        StructType.of(
+                            optional(
+                                3,
+                                "struct3",
+                                StructType.of(
+                                    optional(
+                                        4,
+                                        "struct4",
+                                        StructType.of(
+                                            optional(
+                                                5,
+                                                "struct5",
+                                                StructType.of(
+                                                    optional(
+                                                        6,
+                                                        "struct6",
+                                                        StructType.of(
+                                                            optional(
+                                                                7,
+                                                                "aString",
+                                                                StringType.get()))))))))))))));
+    UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+    EvolveSchemaVisitor.visit(updateApi, new Schema(), targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testAddNestedMaps() {
+    Schema targetSchema =
+        new Schema(
+            optional(
+                1,
+                "struct",
+                MapType.ofOptional(
+                    2,
+                    3,
+                    StringType.get(),
+                    MapType.ofOptional(
+                        4,
+                        5,
+                        StringType.get(),
+                        MapType.ofOptional(
+                            6,
+                            7,
+                            StringType.get(),
+                            MapType.ofOptional(
+                                8,
+                                9,
+                                StringType.get(),
+                                MapType.ofOptional(
+                                    10,
+                                    11,
+                                    StringType.get(),
+                                    MapType.ofOptional(
+                                        12, 13, StringType.get(), StringType.get()))))))));
+    UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+    EvolveSchemaVisitor.visit(updateApi, new Schema(), targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testDetectInvalidTopLevelList() {
+    Schema currentSchema =
+        new Schema(optional(1, "aList", ListType.ofOptional(2, StringType.get())));
+    Schema targetSchema = new Schema(optional(1, "aList", ListType.ofOptional(2, LongType.get())));
+    assertThatThrownBy(
+            () ->
+                EvolveSchemaVisitor.visit(
+                    loadUpdateApi(currentSchema, 2), currentSchema, targetSchema))
+        .hasMessage("Cannot change column type: aList.element: string -> long")
+        .isInstanceOf(IllegalArgumentException.class);
+  }
+
+  @Test
+  public void testDetectInvalidTopLevelMapValue() {
+
+    Schema currentSchema =
+        new Schema(
+            optional(1, "aMap", MapType.ofOptional(2, 3, StringType.get(), StringType.get())));
+    Schema targetSchema =
+        new Schema(optional(1, "aMap", MapType.ofOptional(2, 3, StringType.get(), LongType.get())));
+
+    assertThatThrownBy(
+            () ->
+                EvolveSchemaVisitor.visit(
+                    loadUpdateApi(currentSchema, 3), currentSchema, targetSchema))
+        .hasMessage("Cannot change column type: aMap.value: string -> long")
+        .isInstanceOf(IllegalArgumentException.class);
+  }
+
+  @Test
+  public void testDetectInvalidTopLevelMapKey() {
+    Schema currentSchema =
+        new Schema(
+            optional(1, "aMap", MapType.ofOptional(2, 3, StringType.get(), StringType.get())));
+    Schema targetSchema =
+        new Schema(optional(1, "aMap", MapType.ofOptional(2, 3, UUIDType.get(), StringType.get())));
+    assertThatThrownBy(
+            () ->
+                EvolveSchemaVisitor.visit(
+                    loadUpdateApi(currentSchema, 3), currentSchema, targetSchema))
+        .hasMessage("Cannot change column type: aMap.key: string -> uuid")
+        .isInstanceOf(IllegalArgumentException.class);
+  }
+
+  @Test
+  // int 32-bit signed integers -> Can promote to long
+  public void testTypePromoteIntegerToLong() {
+    Schema currentSchema = new Schema(required(1, "aCol", IntegerType.get()));
+    Schema targetSchema = new Schema(required(1, "aCol", LongType.get()));
+
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 0);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    Schema applied = updateApi.apply();
+    assertThat(applied.asStruct().fields().size()).isEqualTo(1);
+    assertThat(applied.asStruct().fields().get(0).type()).isEqualTo(LongType.get());
+  }
+
+  @Test
+  // float 32-bit IEEE 754 floating point -> Can promote to double
+  public void testTypePromoteFloatToDouble() {
+    Schema currentSchema = new Schema(required(1, "aCol", FloatType.get()));
+    Schema targetSchema = new Schema(required(1, "aCol", DoubleType.get()));
+
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 0);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    Schema applied = updateApi.apply();
+    assertThat(applied.asStruct().fields().size()).isEqualTo(1);
+    assertThat(applied.asStruct().fields().get(0).type()).isEqualTo(DoubleType.get());
+  }
+
+  @Test
+  public void testInvalidTypePromoteDoubleToFloat() {
+    Schema currentSchema = new Schema(required(1, "aCol", DoubleType.get()));
+    Schema targetSchema = new Schema(required(1, "aCol", FloatType.get()));
+    assertThatThrownBy(
+            () ->
+                EvolveSchemaVisitor.visit(
+                    loadUpdateApi(currentSchema, 3), currentSchema, targetSchema))
+        .hasMessage("Cannot change column type: aCol: double -> float")
+        .isInstanceOf(IllegalArgumentException.class);
+  }
+
+  @Test
+  // decimal(P,S) Fixed-point decimal; precision P, scale S -> Scale is fixed [1], precision must be
+  // 38 or less
+  public void testTypePromoteDecimalToFixedScaleWithWiderPrecision() {
+    Schema currentSchema = new Schema(required(1, "aCol", DecimalType.of(20, 1)));
+    Schema targetSchema = new Schema(required(1, "aCol", DecimalType.of(22, 1)));
+
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 1);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testAddPrimitiveToNestedStruct() {
+    Schema existingSchema =
+        new Schema(
+            required(
+                1,
+                "struct1",
+                StructType.of(
+                    optional(
+                        2,
+                        "struct2",
+                        StructType.of(
+                            optional(
+                                3,
+                                "list",
+                                ListType.ofOptional(
+                                    4,
+                                    StructType.of(optional(5, "number", IntegerType.get())))))))));
+
+    Schema targetSchema =
+        new Schema(
+            required(
+                1,
+                "struct1",
+                StructType.of(
+                    optional(
+                        2,
+                        "struct2",
+                        StructType.of(
+                            optional(
+                                3,
+                                "list",
+                                ListType.ofOptional(
+                                    4,
+                                    StructType.of(
+                                        optional(5, "number", LongType.get()),
+                                        optional(6, "time", TimeType.get())))))))));
+
+    UpdateSchema updateApi = loadUpdateApi(existingSchema, 5);
+    EvolveSchemaVisitor.visit(updateApi, existingSchema, targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testReplaceListWithPrimitive() {
+    Schema currentSchema =
+        new Schema(optional(1, "aColumn", ListType.ofOptional(2, StringType.get())));
+    Schema targetSchema = new Schema(optional(1, "aColumn", StringType.get()));
+    assertThatThrownBy(
+            () ->
+                EvolveSchemaVisitor.visit(
+                    loadUpdateApi(currentSchema, 3), currentSchema, targetSchema))
+        .hasMessage("Cannot change column type: aColumn: list<string> -> string")
+        .isInstanceOf(IllegalArgumentException.class);
+  }
+
+  @Test
+  public void addNewTopLevelStruct() {
+    Schema currentSchema =
+        new Schema(
+            optional(
+                1,
+                "map1",
+                MapType.ofOptional(
+                    2,
+                    3,
+                    StringType.get(),
+                    ListType.ofOptional(
+                        4, StructType.of(optional(5, "string1", StringType.get()))))));
+
+    Schema targetSchema =
+        new Schema(
+            optional(
+                1,
+                "map1",
+                MapType.ofOptional(
+                    2,
+                    3,
+                    StringType.get(),
+                    ListType.ofOptional(
+                        4, StructType.of(optional(5, "string1", StringType.get()))))),
+            optional(
+                6,
+                "struct1",
+                StructType.of(
+                    optional(7, "d1", StructType.of(optional(8, "d2", StringType.get()))))));
+
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 5);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testAppendNestedStruct() {
+    Schema currentSchema =
+        new Schema(
+            required(
+                1,
+                "s1",
+                StructType.of(
+                    optional(
+                        2,
+                        "s2",
+                        StructType.of(
+                            optional(
+                                3, "s3", StructType.of(optional(4, "s4", StringType.get()))))))));
+
+    Schema targetSchema =
+        new Schema(
+            required(
+                1,
+                "s1",
+                StructType.of(
+                    optional(
+                        2,
+                        "s2",
+                        StructType.of(
+                            optional(3, "s3", StructType.of(optional(4, "s4", StringType.get()))),
+                            optional(
+                                5,
+                                "repeat",
+                                StructType.of(
+                                    optional(
+                                        6,
+                                        "s1",
+                                        StructType.of(
+                                            optional(
+                                                7,
+                                                "s2",
+                                                StructType.of(
+                                                    optional(
+                                                        8,
+                                                        "s3",
+                                                        StructType.of(
+                                                            optional(
+                                                                9,
+                                                                "s4",
+                                                                StringType.get()))))))))))))));
+
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 4);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testMakeNestedStructOptional() {
+    Schema currentSchema = getNestedSchemaWithOptionalModifier(false);
+    Schema targetSchema =
+        new Schema(
+            required(
+                1,
+                "s1",
+                StructType.of(
+                    optional(
+                        2,
+                        "s2",
+                        StructType.of(
+                            optional(
+                                3, "s3", StructType.of(optional(4, "s4", StringType.get()))))))));
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 9);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    assertThat(getNestedSchemaWithOptionalModifier(true).asStruct())
+        .isEqualTo(updateApi.apply().asStruct());
+  }
+
+  private static Schema getNestedSchemaWithOptionalModifier(boolean nestedIsOptional) {
+    return new Schema(
+        required(
+            1,
+            "s1",
+            StructType.of(
+                optional(
+                    2,
+                    "s2",
+                    StructType.of(
+                        optional(3, "s3", StructType.of(optional(4, "s4", StringType.get()))),
+                        of(
+                            5,
+                            nestedIsOptional,
+                            "repeat",
+                            StructType.of(
+                                optional(
+                                    6,
+                                    "s1",
+                                    StructType.of(
+                                        optional(
+                                            7,
+                                            "s2",
+                                            StructType.of(
+                                                optional(
+                                                    8,
+                                                    "s3",
+                                                    StructType.of(
+                                                        optional(
+                                                            9, "s4", StringType.get()))))))))))))));
+  }
+
+  private static UpdateSchema loadUpdateApi(Schema schema, int lastColumnId) {
+    try {
+      Constructor<?> constructor =
+          TestEvolveSchemaVisitor.class
+              .getClassLoader()
+              .loadClass("org.apache.iceberg.SchemaUpdate")
+              .getDeclaredConstructor(Schema.class, int.class);
+      constructor.setAccessible(true);
+      return (UpdateSchema) constructor.newInstance(schema, lastColumnId);
+    } catch (Exception e) {
+      throw new RuntimeException("Failed to instantiate SchemaUpdate class", e);
+    }
+  }
+}
diff --git a/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestPartitionSpecEvolution.java b/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestPartitionSpecEvolution.java
new file mode 100644
index 000000000000..3e7025de6f91
--- /dev/null
+++ b/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestPartitionSpecEvolution.java
@@ -0,0 +1,188 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+import org.apache.iceberg.PartitionSpec;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.types.Types;
+import org.junit.jupiter.api.Test;
+
+public class TestPartitionSpecEvolution {
+
+  @Test
+  void testCompatible() {
+    Schema schema =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema).bucket("id", 10).build();
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema).bucket("id", 10).build();
+
+    // Happy case, source ids and names match
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isTrue();
+  }
+
+  @Test
+  void testNotCompatibleDifferentTransform() {
+    Schema schema =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema).bucket("id", 10).build();
+    // Same spec als spec1 but different number of buckets
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema).bucket("id", 23).build();
+
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isFalse();
+  }
+
+  @Test
+  void testNotCompatibleMoreFields() {
+    Schema schema =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema).bucket("id", 10).build();
+    // Additional field
+    PartitionSpec spec2 =
+        PartitionSpec.builderFor(schema).bucket("id", 10).truncate("data", 1).build();
+
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isFalse();
+  }
+
+  @Test
+  void testCompatibleWithNonMatchingSourceIds() {
+    Schema schema1 =
+        new Schema(
+            // Use zero-based field ids
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema1).bucket("id", 10).build();
+
+    Schema schema2 =
+        new Schema(
+            Types.NestedField.required(1, "id", Types.IntegerType.get()),
+            Types.NestedField.required(2, "data", Types.StringType.get()));
+
+    // Same spec als spec1 but bound to a different schema
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema2).bucket("id", 10).build();
+
+    // Compatible because the source names match
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isTrue();
+  }
+
+  @Test
+  void testPartitionSpecEvolution() {
+    Schema schema1 =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema1).bucket("id", 10).build();
+
+    Schema schema2 =
+        new Schema(
+            Types.NestedField.required(1, "id", Types.IntegerType.get()),
+            Types.NestedField.required(2, "data", Types.StringType.get()));
+
+    // Change num buckets
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema2).bucket("id", 23).build();
+
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isFalse();
+    PartitionSpecEvolution.PartitionSpecChanges result =
+        PartitionSpecEvolution.evolve(spec1, spec2);
+
+    assertThat(result.termsToAdd().toString()).isEqualTo("[bucket[23](ref(name=\"id\"))]");
+    assertThat(result.termsToRemove().toString()).isEqualTo("[bucket[10](ref(name=\"id\"))]");
+  }
+
+  @Test
+  void testPartitionSpecEvolutionAddField() {
+    Schema schema =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema).build();
+    // Add field
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema).bucket("id", 23).build();
+
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isFalse();
+    PartitionSpecEvolution.PartitionSpecChanges result =
+        PartitionSpecEvolution.evolve(spec1, spec2);
+
+    assertThat(result.termsToAdd().toString()).isEqualTo("[bucket[23](ref(name=\"id\"))]");
+    assertThat(result.termsToRemove().toString()).isEqualTo("[]");
+  }
+
+  @Test
+  void testPartitionSpecEvolutionRemoveField() {
+    Schema schema =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema).bucket("id", 23).build();
+    // Remove field
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema).build();
+
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isFalse();
+    PartitionSpecEvolution.PartitionSpecChanges result =
+        PartitionSpecEvolution.evolve(spec1, spec2);
+
+    assertThat(result.termsToAdd().toString()).isEqualTo("[]");
+    assertThat(result.termsToRemove().toString()).isEqualTo("[bucket[23](ref(name=\"id\"))]");
+  }
+
+  @Test
+  void testPartitionSpecEvolutionWithNestedFields() {
+    Schema schema1 =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(
+                1,
+                "data",
+                Types.StructType.of(Types.NestedField.required(2, "str", Types.StringType.get()))));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema1).bucket("data.str", 10).build();
+
+    Schema schema2 =
+        new Schema(
+            Types.NestedField.required(1, "id", Types.IntegerType.get()),
+            Types.NestedField.required(
+                2,
+                "data",
+                Types.StructType.of(Types.NestedField.required(3, "str", Types.StringType.get()))));
+
+    // Change num buckets
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema2).bucket("data.str", 23).build();
+
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isFalse();
+    PartitionSpecEvolution.PartitionSpecChanges result =
+        PartitionSpecEvolution.evolve(spec1, spec2);
+
+    assertThat(result.termsToAdd().toString()).isEqualTo("[bucket[23](ref(name=\"data.str\"))]");
+    assertThat(result.termsToRemove().toString()).isEqualTo("[bucket[10](ref(name=\"data.str\"))]");
+  }
+}
diff --git a/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestTableMetadataCache.java b/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestTableMetadataCache.java
new file mode 100644
index 000000000000..cedae887041e
--- /dev/null
+++ b/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestTableMetadataCache.java
@@ -0,0 +1,94 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+import org.apache.commons.lang3.SerializationUtils;
+import org.apache.iceberg.PartitionSpec;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.catalog.Catalog;
+import org.apache.iceberg.catalog.TableIdentifier;
+import org.apache.iceberg.flink.sink.TestFlinkIcebergSinkBase;
+import org.apache.iceberg.types.Types;
+import org.junit.jupiter.api.Test;
+
+public class TestTableMetadataCache extends TestFlinkIcebergSinkBase {
+
+  static final Schema SCHEMA =
+      new Schema(
+          Types.NestedField.optional(1, "id", Types.IntegerType.get()),
+          Types.NestedField.optional(2, "data", Types.StringType.get()));
+
+  static final Schema SCHEMA2 =
+      new Schema(
+          Types.NestedField.optional(1, "id", Types.IntegerType.get()),
+          Types.NestedField.optional(2, "data", Types.StringType.get()),
+          Types.NestedField.optional(3, "extra", Types.StringType.get()));
+
+  @Test
+  void testCaching() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("default.myTable");
+    catalog.createTable(tableIdentifier, SCHEMA);
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+
+    Schema schema1 = cache.schema(tableIdentifier, SCHEMA).f0;
+    assertThat(schema1.sameSchema(SCHEMA)).isTrue();
+    assertThat(cache.schema(tableIdentifier, SerializationUtils.clone(SCHEMA)).f0)
+        .isEqualTo(schema1);
+
+    assertThat(cache.schema(tableIdentifier, SCHEMA2)).isEqualTo(TableMetadataCache.NOT_FOUND);
+
+    schema1 = cache.schema(tableIdentifier, SCHEMA).f0;
+    assertThat(cache.schema(tableIdentifier, SerializationUtils.clone(SCHEMA)).f0)
+        .isEqualTo(schema1);
+  }
+
+  @Test
+  void testCacheInvalidationAfterSchemaChange() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("default.myTable");
+    catalog.createTable(tableIdentifier, SCHEMA);
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    Schema schema1 = cache.schema(tableIdentifier, SCHEMA).f0;
+    assertThat(schema1.sameSchema(SCHEMA)).isTrue();
+
+    catalog.dropTable(tableIdentifier);
+    catalog.createTable(tableIdentifier, SCHEMA2);
+    tableUpdater.update(tableIdentifier, "main", SCHEMA2, PartitionSpec.unpartitioned());
+
+    Schema schema2 = cache.schema(tableIdentifier, SCHEMA2).f0;
+    assertThat(schema2.sameSchema(SCHEMA2)).isTrue();
+  }
+
+  @Test
+  void testCachingDisabled() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("default.myTable");
+    catalog.createTable(tableIdentifier, SCHEMA);
+    TableMetadataCache cache = new TableMetadataCache(catalog, 0, Long.MAX_VALUE);
+
+    // Cleanup routine doesn't run after every write
+    cache.getInternalCache().cleanUp();
+    assertThat(cache.getInternalCache().estimatedSize()).isEqualTo(0);
+  }
+}
diff --git a/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestTableUpdater.java b/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestTableUpdater.java
new file mode 100644
index 000000000000..f7a3596462f1
--- /dev/null
+++ b/flink/v1.19/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestTableUpdater.java
@@ -0,0 +1,160 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+import org.apache.flink.api.java.tuple.Tuple2;
+import org.apache.flink.api.java.tuple.Tuple3;
+import org.apache.iceberg.PartitionSpec;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.Table;
+import org.apache.iceberg.catalog.Catalog;
+import org.apache.iceberg.catalog.TableIdentifier;
+import org.apache.iceberg.flink.sink.TestFlinkIcebergSinkBase;
+import org.apache.iceberg.types.Types;
+import org.junit.jupiter.api.Test;
+
+public class TestTableUpdater extends TestFlinkIcebergSinkBase {
+
+  static final Schema SCHEMA =
+      new Schema(
+          Types.NestedField.optional(1, "id", Types.IntegerType.get()),
+          Types.NestedField.optional(2, "data", Types.StringType.get()));
+
+  static final Schema SCHEMA2 =
+      new Schema(
+          Types.NestedField.optional(1, "id", Types.IntegerType.get()),
+          Types.NestedField.optional(2, "data", Types.StringType.get()),
+          Types.NestedField.optional(3, "extra", Types.StringType.get()));
+
+  @Test
+  void testTableCreation() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("myTable");
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    tableUpdater.update(tableIdentifier, "main", SCHEMA, PartitionSpec.unpartitioned());
+    assertThat(catalog.tableExists(tableIdentifier)).isTrue();
+
+    Tuple2<Schema, CompareSchemasVisitor.Result> cachedSchema =
+        cache.schema(tableIdentifier, SCHEMA);
+    assertThat(cachedSchema.f0.sameSchema(SCHEMA)).isTrue();
+  }
+
+  @Test
+  void testTableAlreadyExists() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("myTable");
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    // Make the table non-existent in cache
+    cache.exists(tableIdentifier);
+    // Create the table
+    catalog.createTable(tableIdentifier, SCHEMA);
+    // Make sure that the cache is invalidated and the table refreshed without an error
+    Tuple3<Schema, CompareSchemasVisitor.Result, PartitionSpec> result =
+        tableUpdater.update(tableIdentifier, "main", SCHEMA, PartitionSpec.unpartitioned());
+    assertThat(result.f0.sameSchema(SCHEMA)).isTrue();
+    assertThat(result.f1).isEqualTo(CompareSchemasVisitor.Result.SAME);
+    assertThat(result.f2).isEqualTo(PartitionSpec.unpartitioned());
+  }
+
+  @Test
+  void testBranchCreationAndCaching() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("myTable");
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    catalog.createTable(tableIdentifier, SCHEMA);
+    tableUpdater.update(tableIdentifier, "myBranch", SCHEMA, PartitionSpec.unpartitioned());
+    TableMetadataCache.CacheItem cacheItem = cache.getInternalCache().getIfPresent(tableIdentifier);
+    assertThat(cacheItem).isNotNull();
+
+    tableUpdater.update(tableIdentifier, "myBranch", SCHEMA, PartitionSpec.unpartitioned());
+    assertThat(cache.getInternalCache().getIfPresent(tableIdentifier)).isEqualTo(cacheItem);
+  }
+
+  @Test
+  void testSpecCreation() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("myTable");
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    PartitionSpec spec = PartitionSpec.builderFor(SCHEMA).bucket("data", 10).build();
+    Tuple3<Schema, CompareSchemasVisitor.Result, PartitionSpec> result =
+        tableUpdater.update(tableIdentifier, "main", SCHEMA, spec);
+
+    Table table = catalog.loadTable(tableIdentifier);
+    assertThat(table).isNotNull();
+    assertThat(table.spec()).isEqualTo(spec);
+  }
+
+  @Test
+  void testInvalidateOldCacheEntryOnUpdate() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("default.myTable");
+    catalog.createTable(tableIdentifier, SCHEMA);
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    cache.schema(tableIdentifier, SCHEMA);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    Schema updated =
+        tableUpdater.update(tableIdentifier, "main", SCHEMA2, PartitionSpec.unpartitioned()).f0;
+    assertThat(updated.sameSchema(SCHEMA2));
+    assertThat(cache.schema(tableIdentifier, SCHEMA2).f0.sameSchema(SCHEMA2)).isTrue();
+  }
+
+  @Test
+  void testLastResultInvalidation() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("default.myTable");
+    catalog.createTable(tableIdentifier, SCHEMA);
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    // Initialize cache
+    tableUpdater.update(tableIdentifier, "main", SCHEMA, PartitionSpec.unpartitioned());
+
+    // Update table behind the scenes
+    catalog.dropTable(tableIdentifier);
+    catalog.createTable(tableIdentifier, SCHEMA2);
+
+    // Cache still stores the old information
+    assertThat(cache.schema(tableIdentifier, SCHEMA2).f1)
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+
+    assertThat(
+            tableUpdater.update(tableIdentifier, "main", SCHEMA2, PartitionSpec.unpartitioned()).f1)
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+
+    // Last result cache should be cleared
+    assertThat(
+            cache
+                .getInternalCache()
+                .getIfPresent(tableIdentifier)
+                .getSchemaInfo()
+                .getLastResult(SCHEMA2))
+        .isNull();
+  }
+}
diff --git a/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/CompareSchemasVisitor.java b/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/CompareSchemasVisitor.java
new file mode 100644
index 000000000000..bb0d32f8f644
--- /dev/null
+++ b/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/CompareSchemasVisitor.java
@@ -0,0 +1,266 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import java.util.List;
+import java.util.Map;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.relocated.com.google.common.collect.Maps;
+import org.apache.iceberg.schema.SchemaWithPartnerVisitor;
+import org.apache.iceberg.types.Type;
+import org.apache.iceberg.types.Types;
+
+/**
+ * Visitor class which compares an input schema to a table schema and emits a compatibility {@link
+ * Result}.
+ *
+ * <ul>
+ *   <li>SAME: The two schemas are semantically identical
+ *   <li>DATA_CONVERSION_NEEDED: We can evolve the data associated with the input schema to match
+ *       the table schema.
+ *   <li>SCHEMA_UPDATE_NEEDED: We need to migrate the table schema to match the input schema.
+ * </ul>
+ *
+ * The input schema fields are compared to the table schema via their names.
+ */
+public class CompareSchemasVisitor
+    extends SchemaWithPartnerVisitor<Integer, CompareSchemasVisitor.Result> {
+
+  private final Schema tableSchema;
+
+  private CompareSchemasVisitor(Schema tableSchema) {
+    this.tableSchema = tableSchema;
+  }
+
+  public static Result visit(Schema dataSchema, Schema tableSchema) {
+    return visit(dataSchema, tableSchema, true);
+  }
+
+  public static Result visit(Schema dataSchema, Schema tableSchema, boolean caseSensitive) {
+    return visit(
+        dataSchema,
+        -1,
+        new CompareSchemasVisitor(tableSchema),
+        new PartnerIdByNameAccessors(tableSchema, caseSensitive));
+  }
+
+  @Override
+  public Result schema(Schema dataSchema, Integer tableSchemaId, Result downstream) {
+    if (tableSchemaId == null) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    return downstream;
+  }
+
+  @Override
+  public Result struct(Types.StructType struct, Integer tableSchemaId, List<Result> fields) {
+    if (tableSchemaId == null) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    Result result = fields.stream().reduce(Result::merge).orElse(Result.SCHEMA_UPDATE_NEEDED);
+
+    if (result == Result.SCHEMA_UPDATE_NEEDED) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    Type tableSchemaType =
+        tableSchemaId == -1 ? tableSchema.asStruct() : tableSchema.findField(tableSchemaId).type();
+    if (!tableSchemaType.isStructType()) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    if (struct.fields().size() != tableSchemaType.asStructType().fields().size()) {
+      return Result.DATA_CONVERSION_NEEDED;
+    }
+
+    for (int i = 0; i < struct.fields().size(); ++i) {
+      if (!struct
+          .fields()
+          .get(i)
+          .name()
+          .equals(tableSchemaType.asStructType().fields().get(i).name())) {
+        return Result.DATA_CONVERSION_NEEDED;
+      }
+    }
+
+    return result;
+  }
+
+  @Override
+  public Result field(Types.NestedField field, Integer tableSchemaId, Result typeResult) {
+    if (tableSchemaId == null) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    if (typeResult != Result.SAME) {
+      return typeResult;
+    }
+
+    if (tableSchema.findField(tableSchemaId).isRequired() && field.isOptional()) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    } else {
+      return Result.SAME;
+    }
+  }
+
+  @Override
+  public Result list(Types.ListType list, Integer tableSchemaId, Result elementsResult) {
+    if (tableSchemaId == null) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    return elementsResult;
+  }
+
+  @Override
+  public Result map(
+      Types.MapType map, Integer tableSchemaId, Result keyResult, Result valueResult) {
+    if (tableSchemaId == null) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    return keyResult.merge(valueResult);
+  }
+
+  @Override
+  @SuppressWarnings("checkstyle:CyclomaticComplexity")
+  public Result primitive(Type.PrimitiveType primitive, Integer tableSchemaId) {
+    if (tableSchemaId == null) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    Type tableSchemaType = tableSchema.findField(tableSchemaId).type();
+    if (!tableSchemaType.isPrimitiveType()) {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+
+    Type.PrimitiveType tableSchemaPrimitiveType = tableSchemaType.asPrimitiveType();
+    if (primitive.equals(tableSchemaPrimitiveType)) {
+      return Result.SAME;
+    } else if (primitive.equals(Types.IntegerType.get())
+        && tableSchemaPrimitiveType.equals(Types.LongType.get())) {
+      return Result.DATA_CONVERSION_NEEDED;
+    } else if (primitive.equals(Types.FloatType.get())
+        && tableSchemaPrimitiveType.equals(Types.DoubleType.get())) {
+      return Result.DATA_CONVERSION_NEEDED;
+    } else if (primitive.equals(Types.DateType.get())
+        && tableSchemaPrimitiveType.equals(Types.TimestampType.withoutZone())) {
+      return Result.DATA_CONVERSION_NEEDED;
+    } else if (primitive.typeId() == Type.TypeID.DECIMAL
+        && tableSchemaPrimitiveType.typeId() == Type.TypeID.DECIMAL) {
+      Types.DecimalType dataType = (Types.DecimalType) primitive;
+      Types.DecimalType tableType = (Types.DecimalType) tableSchemaPrimitiveType;
+      return dataType.scale() == tableType.scale() && dataType.precision() < tableType.precision()
+          ? Result.DATA_CONVERSION_NEEDED
+          : Result.SCHEMA_UPDATE_NEEDED;
+    } else {
+      return Result.SCHEMA_UPDATE_NEEDED;
+    }
+  }
+
+  static class PartnerIdByNameAccessors implements PartnerAccessors<Integer> {
+    private final Schema tableSchema;
+    private boolean caseSensitive = true;
+
+    PartnerIdByNameAccessors(Schema tableSchema) {
+      this.tableSchema = tableSchema;
+    }
+
+    private PartnerIdByNameAccessors(Schema tableSchema, boolean caseSensitive) {
+      this(tableSchema);
+      this.caseSensitive = caseSensitive;
+    }
+
+    @Override
+    public Integer fieldPartner(Integer tableSchemaFieldId, int fieldId, String name) {
+      Types.StructType struct;
+      if (tableSchemaFieldId == -1) {
+        struct = tableSchema.asStruct();
+      } else {
+        struct = tableSchema.findField(tableSchemaFieldId).type().asStructType();
+      }
+
+      Types.NestedField field =
+          caseSensitive ? struct.field(name) : struct.caseInsensitiveField(name);
+      if (field != null) {
+        return field.fieldId();
+      }
+
+      return null;
+    }
+
+    @Override
+    public Integer mapKeyPartner(Integer tableSchemaMapId) {
+      Types.NestedField mapField = tableSchema.findField(tableSchemaMapId);
+      if (mapField != null) {
+        return mapField.type().asMapType().fields().get(0).fieldId();
+      }
+
+      return null;
+    }
+
+    @Override
+    public Integer mapValuePartner(Integer tableSchemaMapId) {
+      Types.NestedField mapField = tableSchema.findField(tableSchemaMapId);
+      if (mapField != null) {
+        return mapField.type().asMapType().fields().get(1).fieldId();
+      }
+
+      return null;
+    }
+
+    @Override
+    public Integer listElementPartner(Integer tableSchemaListId) {
+      Types.NestedField listField = tableSchema.findField(tableSchemaListId);
+      if (listField != null) {
+        return listField.type().asListType().fields().get(0).fieldId();
+      }
+
+      return null;
+    }
+  }
+
+  public enum Result {
+    SAME(0),
+    DATA_CONVERSION_NEEDED(1),
+    SCHEMA_UPDATE_NEEDED(2);
+
+    private static final Map<Integer, Result> BY_ID = Maps.newHashMap();
+
+    static {
+      for (Result e : Result.values()) {
+        if (BY_ID.put(e.id, e) != null) {
+          throw new IllegalArgumentException("Duplicate id: " + e.id);
+        }
+      }
+    }
+
+    private final int id;
+
+    Result(int id) {
+      this.id = id;
+    }
+
+    private Result merge(Result other) {
+      return BY_ID.get(Math.max(this.id, other.id));
+    }
+  }
+}
diff --git a/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/EvolveSchemaVisitor.java b/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/EvolveSchemaVisitor.java
new file mode 100644
index 000000000000..85fd5753919e
--- /dev/null
+++ b/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/EvolveSchemaVisitor.java
@@ -0,0 +1,204 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import java.util.List;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.UpdateSchema;
+import org.apache.iceberg.relocated.com.google.common.base.Preconditions;
+import org.apache.iceberg.schema.SchemaWithPartnerVisitor;
+import org.apache.iceberg.types.Type;
+import org.apache.iceberg.types.Types;
+
+/**
+ * Visitor class that accumulates the set of changes needed to evolve an existing schema into the
+ * target schema. Changes are applied to an {@link UpdateSchema} operation.
+ *
+ * <p>We support:
+ *
+ * <ul>
+ *   <li>Adding new columns
+ *   <li>Widening the type of existing columsn
+ *   <li>Reordering columns
+ * </ul>
+ *
+ * We don't support:
+ *
+ * <ul>
+ *   <li>Dropping columns
+ *   <li>Renaming columns
+ * </ul>
+ *
+ * The reason is that dropping columns would create issues with late / out of order data. Once we
+ * drop fields, we wouldn't be able to easily add them back later without losing the associated
+ * data. Renaming columns is not supported because we compare schemas by name, which doesn't allow
+ * for renaming without additional hints.
+ */
+public class EvolveSchemaVisitor extends SchemaWithPartnerVisitor<Integer, Boolean> {
+
+  private final UpdateSchema api;
+  private final Schema existingSchema;
+  private final Schema targetSchema;
+
+  private EvolveSchemaVisitor(UpdateSchema api, Schema existingSchema, Schema targetSchema) {
+    this.api = api;
+    this.existingSchema = existingSchema;
+    this.targetSchema = targetSchema;
+  }
+
+  /**
+   * Adds changes needed to produce the target schema to an {@link UpdateSchema} operation.
+   *
+   * <p>Changes are accumulated to evolve the existingSchema into a targetSchema.
+   *
+   * @param api an UpdateSchema for adding changes
+   * @param existingSchema an existing schema
+   * @param targetSchema a new schema to compare with the existing
+   */
+  public static void visit(UpdateSchema api, Schema existingSchema, Schema targetSchema) {
+    visit(
+        targetSchema,
+        -1,
+        new EvolveSchemaVisitor(api, existingSchema, targetSchema),
+        new CompareSchemasVisitor.PartnerIdByNameAccessors(existingSchema));
+  }
+
+  @Override
+  public Boolean struct(Types.StructType struct, Integer partnerId, List<Boolean> existingFields) {
+    if (partnerId == null) {
+      return true;
+    }
+
+    // Add, update and order fields in the struct
+    Types.StructType partnerStruct = findFieldType(partnerId).asStructType();
+    String after = null;
+    for (Types.NestedField targetField : struct.fields()) {
+      Types.NestedField nestedField = partnerStruct.field(targetField.name());
+      final String columnName;
+      if (nestedField != null) {
+        updateColumn(nestedField, targetField);
+        columnName = this.existingSchema.findColumnName(nestedField.fieldId());
+      } else {
+        addColumn(partnerId, targetField);
+        columnName = this.targetSchema.findColumnName(targetField.fieldId());
+      }
+
+      setPosition(columnName, after);
+      after = columnName;
+    }
+
+    // Ensure that unused fields are made optional
+    for (Types.NestedField existingField : partnerStruct.fields()) {
+      if (struct.field(existingField.name()) == null) {
+        if (existingField.isRequired()) {
+          this.api.makeColumnOptional(this.existingSchema.findColumnName(existingField.fieldId()));
+        }
+      }
+    }
+
+    return false;
+  }
+
+  @Override
+  public Boolean field(Types.NestedField field, Integer partnerId, Boolean isFieldMissing) {
+    return partnerId == null;
+  }
+
+  @Override
+  public Boolean list(Types.ListType list, Integer partnerId, Boolean isElementMissing) {
+    if (partnerId == null) {
+      return true;
+    }
+
+    Preconditions.checkState(
+        !isElementMissing, "Error traversing schemas: element is missing, but list is present");
+
+    Types.ListType partnerList = findFieldType(partnerId).asListType();
+    updateColumn(partnerList.fields().get(0), list.fields().get(0));
+
+    return false;
+  }
+
+  @Override
+  public Boolean map(
+      Types.MapType map, Integer partnerId, Boolean isKeyMissing, Boolean isValueMissing) {
+    if (partnerId == null) {
+      return true;
+    }
+
+    Preconditions.checkState(
+        !isKeyMissing, "Error traversing schemas: key is missing, but map is present");
+    Preconditions.checkState(
+        !isValueMissing, "Error traversing schemas: value is missing, but map is present");
+
+    Types.MapType partnerMap = findFieldType(partnerId).asMapType();
+    updateColumn(partnerMap.fields().get(0), map.fields().get(0));
+    updateColumn(partnerMap.fields().get(1), map.fields().get(1));
+
+    return false;
+  }
+
+  @Override
+  public Boolean primitive(Type.PrimitiveType primitive, Integer partnerId) {
+    return partnerId == null;
+  }
+
+  private Type findFieldType(int fieldId) {
+    if (fieldId == -1) {
+      return existingSchema.asStruct();
+    } else {
+      return existingSchema.findField(fieldId).type();
+    }
+  }
+
+  private void addColumn(int parentId, Types.NestedField field) {
+    String parentName = targetSchema.findColumnName(parentId);
+    api.addColumn(parentName, field.name(), field.type(), field.doc());
+  }
+
+  private void updateColumn(Types.NestedField existingField, Types.NestedField targetField) {
+    String existingColumnName = this.existingSchema.findColumnName(existingField.fieldId());
+
+    boolean needsOptionalUpdate = targetField.isOptional() && existingField.isRequired();
+    boolean needsTypeUpdate =
+        targetField.type().isPrimitiveType() && !targetField.type().equals(existingField.type());
+    boolean needsDocUpdate =
+        targetField.doc() != null && !targetField.doc().equals(existingField.doc());
+
+    if (needsOptionalUpdate) {
+      api.makeColumnOptional(existingColumnName);
+    }
+
+    if (needsTypeUpdate) {
+      api.updateColumn(existingColumnName, targetField.type().asPrimitiveType());
+    }
+
+    if (needsDocUpdate) {
+      api.updateColumnDoc(existingColumnName, targetField.doc());
+    }
+  }
+
+  private void setPosition(String columnName, String after) {
+    if (after == null) {
+      this.api.moveFirst(columnName);
+    } else {
+      this.api.moveAfter(columnName, after);
+    }
+  }
+}
diff --git a/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/PartitionSpecEvolution.java b/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/PartitionSpecEvolution.java
new file mode 100644
index 000000000000..90b6c7295cb7
--- /dev/null
+++ b/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/PartitionSpecEvolution.java
@@ -0,0 +1,137 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import java.util.List;
+import org.apache.iceberg.PartitionField;
+import org.apache.iceberg.PartitionSpec;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.expressions.Expressions;
+import org.apache.iceberg.expressions.Term;
+import org.apache.iceberg.relocated.com.google.common.base.MoreObjects;
+import org.apache.iceberg.relocated.com.google.common.collect.Iterables;
+import org.apache.iceberg.relocated.com.google.common.collect.Lists;
+
+/** Checks compatibility of PartitionSpecs and evolves one into the other. */
+public class PartitionSpecEvolution {
+
+  private PartitionSpecEvolution() {}
+
+  /**
+   * Checks whether two PartitionSpecs are compatible with each other. Less strict than {@code
+   * PartitionSpec#compatible} in the sense that it tolerates differently named partition fields, as
+   * long as their transforms and field names corresponding to their source ids match.
+   */
+  public static boolean checkCompatibility(PartitionSpec spec1, PartitionSpec spec2) {
+    if (spec1.equals(spec2)) {
+      return true;
+    }
+
+    if (spec1.fields().size() != spec2.fields().size()) {
+      return false;
+    }
+
+    for (int i = 0; i < spec1.fields().size(); i++) {
+      PartitionField field1 = spec1.fields().get(i);
+      PartitionField field2 = spec2.fields().get(i);
+      if (!specFieldsAreCompatible(field1, spec1.schema(), field2, spec2.schema())) {
+        return false;
+      }
+    }
+
+    return true;
+  }
+
+  static PartitionSpecChanges evolve(PartitionSpec currentSpec, PartitionSpec targetSpec) {
+    if (currentSpec.compatibleWith(targetSpec)) {
+      return new PartitionSpecChanges();
+    }
+
+    PartitionSpecChanges result = new PartitionSpecChanges();
+
+    int maxNumFields = Math.max(currentSpec.fields().size(), targetSpec.fields().size());
+    for (int i = 0; i < maxNumFields; i++) {
+      PartitionField currentField = Iterables.get(currentSpec.fields(), i, null);
+      PartitionField targetField = Iterables.get(targetSpec.fields(), i, null);
+
+      if (!specFieldsAreCompatible(
+          currentField, currentSpec.schema(), targetField, targetSpec.schema())) {
+
+        if (currentField != null) {
+          result.remove(toTerm(currentField, currentSpec.schema()));
+        }
+
+        if (targetField != null) {
+          result.add(toTerm(targetField, targetSpec.schema()));
+        }
+      }
+    }
+
+    return result;
+  }
+
+  static class PartitionSpecChanges {
+    private final List<Term> termsToAdd = Lists.newArrayList();
+    private final List<Term> termsToRemove = Lists.newArrayList();
+
+    public void add(Term term) {
+      termsToAdd.add(term);
+    }
+
+    public void remove(Term term) {
+      termsToRemove.add(term);
+    }
+
+    public List<Term> termsToAdd() {
+      return termsToAdd;
+    }
+
+    public List<Term> termsToRemove() {
+      return termsToRemove;
+    }
+
+    public boolean isEmpty() {
+      return termsToAdd.isEmpty() && termsToRemove.isEmpty();
+    }
+
+    @Override
+    public String toString() {
+      return MoreObjects.toStringHelper(PartitionSpecEvolution.class)
+          .add("termsToAdd", termsToAdd)
+          .add("termsToRemove", termsToRemove)
+          .toString();
+    }
+  }
+
+  private static Term toTerm(PartitionField field, Schema schema) {
+    String sourceName = schema.idToName().get(field.sourceId());
+    return Expressions.transform(sourceName, field.transform());
+  }
+
+  private static boolean specFieldsAreCompatible(
+      PartitionField field1, Schema schemaField1, PartitionField field2, Schema schemaField2) {
+    if (field1 == null || field2 == null) {
+      return false;
+    }
+    String firstFieldSourceName = schemaField1.idToName().get(field1.sourceId());
+    String secondFieldSourceName = schemaField2.idToName().get(field2.sourceId());
+    return firstFieldSourceName.equals(secondFieldSourceName)
+        && field1.transform().toString().equals(field2.transform().toString());
+  }
+}
diff --git a/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/TableMetadataCache.java b/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/TableMetadataCache.java
new file mode 100644
index 000000000000..e9c77ea8c809
--- /dev/null
+++ b/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/TableMetadataCache.java
@@ -0,0 +1,261 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import com.github.benmanes.caffeine.cache.Cache;
+import com.github.benmanes.caffeine.cache.Caffeine;
+import java.util.LinkedHashMap;
+import java.util.Map;
+import java.util.Set;
+import org.apache.flink.annotation.Internal;
+import org.apache.flink.annotation.VisibleForTesting;
+import org.apache.flink.api.java.tuple.Tuple2;
+import org.apache.iceberg.PartitionSpec;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.Table;
+import org.apache.iceberg.catalog.Catalog;
+import org.apache.iceberg.catalog.TableIdentifier;
+import org.apache.iceberg.exceptions.NoSuchTableException;
+import org.slf4j.Logger;
+import org.slf4j.LoggerFactory;
+
+/**
+ * TableMetadataCache is responsible for caching table metadata to avoid hitting the catalog too
+ * frequently. We store table identifier, schema, partition spec, and a set of past schema
+ * comparison results of the active table schema against the last input schemas.
+ */
+@Internal
+class TableMetadataCache {
+
+  private static final Logger LOG = LoggerFactory.getLogger(TableMetadataCache.class);
+  private static final int MAX_SCHEMA_COMPARISON_RESULTS_TO_CACHE = 10;
+  private static final Tuple2<Boolean, Exception> EXISTS = Tuple2.of(true, null);
+  private static final Tuple2<Boolean, Exception> NOT_EXISTS = Tuple2.of(false, null);
+  static final Tuple2<Schema, CompareSchemasVisitor.Result> NOT_FOUND =
+      Tuple2.of(null, CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+
+  private final Catalog catalog;
+  private final long refreshMs;
+  private final Cache<TableIdentifier, CacheItem> cache;
+
+  TableMetadataCache(Catalog catalog, int maximumSize, long refreshMs) {
+    this.catalog = catalog;
+    this.refreshMs = refreshMs;
+    this.cache = Caffeine.newBuilder().maximumSize(maximumSize).build();
+  }
+
+  Tuple2<Boolean, Exception> exists(TableIdentifier identifier) {
+    CacheItem cached = cache.getIfPresent(identifier);
+    if (cached != null && Boolean.TRUE.equals(cached.tableExists)) {
+      return EXISTS;
+    } else if (needsRefresh(cached, true)) {
+      return refreshTable(identifier);
+    } else {
+      return NOT_EXISTS;
+    }
+  }
+
+  String branch(TableIdentifier identifier, String branch) {
+    return branch(identifier, branch, true);
+  }
+
+  Tuple2<Schema, CompareSchemasVisitor.Result> schema(TableIdentifier identifier, Schema input) {
+    return schema(identifier, input, true);
+  }
+
+  PartitionSpec spec(TableIdentifier identifier, PartitionSpec spec) {
+    return spec(identifier, spec, true);
+  }
+
+  void update(TableIdentifier identifier, Table table) {
+    cache.put(
+        identifier,
+        new CacheItem(true, table.refs().keySet(), new SchemaInfo(table.schemas()), table.specs()));
+  }
+
+  private String branch(TableIdentifier identifier, String branch, boolean allowRefresh) {
+    CacheItem cached = cache.getIfPresent(identifier);
+    if (cached != null && cached.tableExists && cached.branches.contains(branch)) {
+      return branch;
+    }
+
+    if (needsRefresh(cached, allowRefresh)) {
+      refreshTable(identifier);
+      return branch(identifier, branch, false);
+    } else {
+      return null;
+    }
+  }
+
+  private Tuple2<Schema, CompareSchemasVisitor.Result> schema(
+      TableIdentifier identifier, Schema input, boolean allowRefresh) {
+    CacheItem cached = cache.getIfPresent(identifier);
+    Schema compatible = null;
+    if (cached != null && cached.tableExists) {
+      // This only works if the {@link Schema#equals(Object)} returns true for the old schema
+      // and a new schema. Performance is paramount as this code is on the hot path. Every other
+      // way for comparing 2 schemas were performing worse than the
+      // {@link CompareByNameVisitor#visit(Schema, Schema, boolean)}, so caching was useless.
+      Tuple2<Schema, CompareSchemasVisitor.Result> lastResult =
+          cached.schema.lastResults.get(input);
+      if (lastResult != null) {
+        return lastResult;
+      }
+
+      for (Map.Entry<Integer, Schema> tableSchema : cached.schema.schemas.entrySet()) {
+        CompareSchemasVisitor.Result result =
+            CompareSchemasVisitor.visit(input, tableSchema.getValue(), true);
+        if (result == CompareSchemasVisitor.Result.SAME) {
+          Tuple2<Schema, CompareSchemasVisitor.Result> newResult =
+              Tuple2.of(tableSchema.getValue(), CompareSchemasVisitor.Result.SAME);
+          cached.schema.update(input, newResult);
+          return newResult;
+        } else if (compatible == null
+            && result == CompareSchemasVisitor.Result.DATA_CONVERSION_NEEDED) {
+          compatible = tableSchema.getValue();
+        }
+      }
+    }
+
+    if (needsRefresh(cached, allowRefresh)) {
+      refreshTable(identifier);
+      return schema(identifier, input, false);
+    } else if (compatible != null) {
+      Tuple2<Schema, CompareSchemasVisitor.Result> newResult =
+          Tuple2.of(compatible, CompareSchemasVisitor.Result.DATA_CONVERSION_NEEDED);
+      cached.schema.update(input, newResult);
+      return newResult;
+    } else if (cached != null && cached.tableExists) {
+      cached.schema.update(input, NOT_FOUND);
+      return NOT_FOUND;
+    } else {
+      return NOT_FOUND;
+    }
+  }
+
+  private PartitionSpec spec(TableIdentifier identifier, PartitionSpec spec, boolean allowRefresh) {
+    CacheItem cached = cache.getIfPresent(identifier);
+    if (cached != null && cached.tableExists) {
+      for (PartitionSpec tableSpec : cached.specs.values()) {
+        if (PartitionSpecEvolution.checkCompatibility(tableSpec, spec)) {
+          return tableSpec;
+        }
+      }
+    }
+
+    if (needsRefresh(cached, allowRefresh)) {
+      refreshTable(identifier);
+      return spec(identifier, spec, false);
+    } else {
+      return null;
+    }
+  }
+
+  private Tuple2<Boolean, Exception> refreshTable(TableIdentifier identifier) {
+    try {
+      Table table = catalog.loadTable(identifier);
+      update(identifier, table);
+      return EXISTS;
+    } catch (NoSuchTableException e) {
+      LOG.debug("Table doesn't exist {}", identifier, e);
+      cache.put(identifier, new CacheItem(false, null, null, null));
+      return Tuple2.of(false, e);
+    }
+  }
+
+  private boolean needsRefresh(CacheItem cacheItem, boolean allowRefresh) {
+    return allowRefresh
+        && (cacheItem == null || cacheItem.created + refreshMs > System.currentTimeMillis());
+  }
+
+  public void invalidate(TableIdentifier identifier) {
+    cache.invalidate(identifier);
+  }
+
+  /** Handles timeout for missing items only. Caffeine performance causes noticeable delays. */
+  static class CacheItem {
+    private final long created = System.currentTimeMillis();
+
+    private final boolean tableExists;
+    private final Set<String> branches;
+    private final SchemaInfo schema;
+    private final Map<Integer, PartitionSpec> specs;
+
+    private CacheItem(
+        boolean tableExists,
+        Set<String> branches,
+        SchemaInfo schema,
+        Map<Integer, PartitionSpec> specs) {
+      this.tableExists = tableExists;
+      this.branches = branches;
+      this.schema = schema;
+      this.specs = specs;
+    }
+
+    @VisibleForTesting
+    SchemaInfo getSchemaInfo() {
+      return schema;
+    }
+  }
+
+  /**
+   * Stores precalculated results for {@link CompareSchemasVisitor#visit(Schema, Schema, boolean)}
+   * in the cache.
+   */
+  static class SchemaInfo {
+    private final Map<Integer, Schema> schemas;
+    private final Map<Schema, Tuple2<Schema, CompareSchemasVisitor.Result>> lastResults;
+
+    private SchemaInfo(Map<Integer, Schema> schemas) {
+      this.schemas = schemas;
+      this.lastResults = new LimitedLinkedHashMap<>();
+    }
+
+    private void update(
+        Schema newLastSchema, Tuple2<Schema, CompareSchemasVisitor.Result> newLastResult) {
+      lastResults.put(newLastSchema, newLastResult);
+    }
+
+    @VisibleForTesting
+    Tuple2<Schema, CompareSchemasVisitor.Result> getLastResult(Schema schema) {
+      return lastResults.get(schema);
+    }
+  }
+
+  @SuppressWarnings("checkstyle:IllegalType")
+  private static class LimitedLinkedHashMap<K, V> extends LinkedHashMap<K, V> {
+    @Override
+    protected boolean removeEldestEntry(Map.Entry<K, V> eldest) {
+      boolean remove = size() > MAX_SCHEMA_COMPARISON_RESULTS_TO_CACHE;
+      if (remove) {
+        LOG.warn(
+            "Performance degraded as records with different schema is generated for the same table. "
+                + "Likely the DynamicRecord.schema is not reused. "
+                + "Reuse the same instance if the record schema is the same to improve performance");
+      }
+
+      return remove;
+    }
+  }
+
+  @VisibleForTesting
+  Cache<TableIdentifier, CacheItem> getInternalCache() {
+    return cache;
+  }
+}
diff --git a/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/TableUpdater.java b/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/TableUpdater.java
new file mode 100644
index 000000000000..40bb66f65125
--- /dev/null
+++ b/flink/v1.20/flink/src/main/java/org/apache/iceberg/flink/sink/dynamic/TableUpdater.java
@@ -0,0 +1,207 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import org.apache.flink.annotation.Internal;
+import org.apache.flink.api.java.tuple.Tuple2;
+import org.apache.flink.api.java.tuple.Tuple3;
+import org.apache.iceberg.PartitionSpec;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.Table;
+import org.apache.iceberg.UpdatePartitionSpec;
+import org.apache.iceberg.UpdateSchema;
+import org.apache.iceberg.catalog.Catalog;
+import org.apache.iceberg.catalog.SupportsNamespaces;
+import org.apache.iceberg.catalog.TableIdentifier;
+import org.apache.iceberg.exceptions.AlreadyExistsException;
+import org.apache.iceberg.exceptions.CommitFailedException;
+import org.apache.iceberg.exceptions.NoSuchNamespaceException;
+import org.slf4j.Logger;
+import org.slf4j.LoggerFactory;
+
+/** Updates the Iceberg tables in case of schema, branch, or partition changes. */
+@Internal
+class TableUpdater {
+
+  private static final Logger LOG = LoggerFactory.getLogger(TableUpdater.class);
+  private final TableMetadataCache cache;
+  private final Catalog catalog;
+
+  TableUpdater(TableMetadataCache cache, Catalog catalog) {
+    this.cache = cache;
+    this.catalog = catalog;
+  }
+
+  /**
+   * Creates or updates a table to make sure that the given branch, schema, spec exists.
+   *
+   * @return a {@link Tuple3} of the new {@link Schema}, the status of the schema compared to the
+   *     requested one, and the new {@link PartitionSpec#specId()}.
+   */
+  Tuple3<Schema, CompareSchemasVisitor.Result, PartitionSpec> update(
+      TableIdentifier tableIdentifier, String branch, Schema schema, PartitionSpec spec) {
+    findOrCreateTable(tableIdentifier, schema, spec);
+    findOrCreateBranch(tableIdentifier, branch);
+    Tuple2<Schema, CompareSchemasVisitor.Result> newSchema =
+        findOrCreateSchema(tableIdentifier, schema);
+    PartitionSpec newSpec = findOrCreateSpec(tableIdentifier, spec);
+    return Tuple3.of(newSchema.f0, newSchema.f1, newSpec);
+  }
+
+  private void findOrCreateTable(TableIdentifier identifier, Schema schema, PartitionSpec spec) {
+    Tuple2<Boolean, Exception> exists = cache.exists(identifier);
+    if (Boolean.FALSE.equals(exists.f0)) {
+      if (exists.f1 instanceof NoSuchNamespaceException) {
+        SupportsNamespaces catalogWithNameSpace = (SupportsNamespaces) catalog;
+        LOG.info("Namespace {} not found during table search. Creating namespace", identifier);
+        try {
+          catalogWithNameSpace.createNamespace(identifier.namespace());
+        } catch (AlreadyExistsException e) {
+          LOG.debug("Namespace {} created concurrently", identifier.namespace(), e);
+        }
+      }
+
+      LOG.info("Table {} not found during table search. Creating table.", identifier);
+      try {
+        Table table = catalog.createTable(identifier, schema, spec);
+        cache.update(identifier, table);
+      } catch (AlreadyExistsException e) {
+        LOG.debug("Table {} created concurrently. Skipping creation.", identifier, e);
+        cache.invalidate(identifier);
+        findOrCreateTable(identifier, schema, spec);
+      }
+    }
+  }
+
+  private void findOrCreateBranch(TableIdentifier identifier, String branch) {
+    String fromCache = cache.branch(identifier, branch);
+    if (fromCache == null) {
+      Table table = catalog.loadTable(identifier);
+      try {
+        table.manageSnapshots().createBranch(branch).commit();
+        LOG.info("Branch {} for {} created", branch, identifier);
+      } catch (CommitFailedException e) {
+        table.refresh();
+        if (table.refs().containsKey(branch)) {
+          LOG.debug("Branch {} concurrently created for {}.", branch, identifier);
+        } else {
+          LOG.error("Failed to create branch {} for {}.", branch, identifier, e);
+          throw e;
+        }
+      }
+
+      cache.update(identifier, table);
+    }
+  }
+
+  private Tuple2<Schema, CompareSchemasVisitor.Result> findOrCreateSchema(
+      TableIdentifier identifier, Schema schema) {
+    Tuple2<Schema, CompareSchemasVisitor.Result> fromCache = cache.schema(identifier, schema);
+    if (fromCache.f1 != CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED) {
+      return fromCache;
+    } else {
+      Table table = catalog.loadTable(identifier);
+      Schema tableSchema = table.schema();
+      CompareSchemasVisitor.Result result = CompareSchemasVisitor.visit(schema, tableSchema, true);
+      switch (result) {
+        case SAME:
+        case DATA_CONVERSION_NEEDED:
+          cache.update(identifier, table);
+          return Tuple2.of(tableSchema, result);
+        case SCHEMA_UPDATE_NEEDED:
+          LOG.info(
+              "Triggering schema update for table {} {} to {}", identifier, tableSchema, schema);
+          UpdateSchema updateApi = table.updateSchema();
+          EvolveSchemaVisitor.visit(updateApi, tableSchema, schema);
+
+          try {
+            updateApi.commit();
+            cache.update(identifier, table);
+            Tuple2<Schema, CompareSchemasVisitor.Result> comparisonAfterMigration =
+                cache.schema(identifier, schema);
+            Schema newSchema = comparisonAfterMigration.f0;
+            LOG.info("Table {} schema updated from {} to {}", identifier, tableSchema, newSchema);
+            return comparisonAfterMigration;
+          } catch (CommitFailedException e) {
+            cache.invalidate(identifier);
+            Tuple2<Schema, CompareSchemasVisitor.Result> newSchema =
+                cache.schema(identifier, schema);
+            if (newSchema.f1 != CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED) {
+              LOG.debug("Table {} schema updated concurrently to {}", identifier, schema);
+              return newSchema;
+            } else {
+              LOG.error(
+                  "Schema update failed for {} from {} to {}", identifier, tableSchema, schema, e);
+              throw e;
+            }
+          }
+        default:
+          throw new IllegalArgumentException("Unknown comparison result");
+      }
+    }
+  }
+
+  private PartitionSpec findOrCreateSpec(TableIdentifier identifier, PartitionSpec targetSpec) {
+    PartitionSpec currentSpec = cache.spec(identifier, targetSpec);
+    if (currentSpec != null) {
+      return currentSpec;
+    }
+
+    Table table = catalog.loadTable(identifier);
+    currentSpec = table.spec();
+
+    PartitionSpecEvolution.PartitionSpecChanges result =
+        PartitionSpecEvolution.evolve(currentSpec, targetSpec);
+    if (result.isEmpty()) {
+      LOG.info("Returning equivalent existing spec {} for {}", currentSpec, targetSpec);
+      return currentSpec;
+    }
+
+    LOG.info(
+        "Spec for table {} has been altered. Updating from {} to {}",
+        identifier,
+        currentSpec,
+        targetSpec);
+    UpdatePartitionSpec updater = table.updateSpec();
+    result.termsToRemove().forEach(updater::removeField);
+    result.termsToAdd().forEach(updater::addField);
+
+    try {
+      updater.commit();
+      cache.update(identifier, table);
+    } catch (CommitFailedException e) {
+      cache.invalidate(identifier);
+      PartitionSpec newSpec = cache.spec(identifier, targetSpec);
+      result = PartitionSpecEvolution.evolve(targetSpec, newSpec);
+      if (result.isEmpty()) {
+        LOG.debug("Table {} partition spec updated concurrently to {}", identifier, newSpec);
+        return newSpec;
+      } else {
+        LOG.error(
+            "Partition spec update failed for {} from {} to {}",
+            identifier,
+            currentSpec,
+            targetSpec,
+            e);
+        throw e;
+      }
+    }
+    return cache.spec(identifier, targetSpec);
+  }
+}
diff --git a/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestCompareSchemasVisitor.java b/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestCompareSchemasVisitor.java
new file mode 100644
index 000000000000..487b0ee7d94a
--- /dev/null
+++ b/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestCompareSchemasVisitor.java
@@ -0,0 +1,209 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import static org.apache.iceberg.types.Types.NestedField.optional;
+import static org.apache.iceberg.types.Types.NestedField.required;
+import static org.assertj.core.api.Assertions.assertThat;
+
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.types.Types.IntegerType;
+import org.apache.iceberg.types.Types.ListType;
+import org.apache.iceberg.types.Types.LongType;
+import org.apache.iceberg.types.Types.MapType;
+import org.apache.iceberg.types.Types.StringType;
+import org.apache.iceberg.types.Types.StructType;
+import org.junit.jupiter.api.Test;
+
+class TestCompareSchemasVisitor {
+
+  @Test
+  void testSchema() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", IntegerType.get(), "comment"),
+                    optional(2, "data", StringType.get()),
+                    optional(3, "extra", StringType.get())),
+                new Schema(
+                    optional(1, "id", IntegerType.get(), "comment"),
+                    optional(2, "data", StringType.get()),
+                    optional(3, "extra", StringType.get()))))
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+  }
+
+  @Test
+  void testSchemaDifferentId() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(1, "data", StringType.get()),
+                    optional(2, "extra", StringType.get())),
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(2, "data", StringType.get()),
+                    optional(3, "extra", StringType.get()))))
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+  }
+
+  @Test
+  void testSchemaDifferent() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(1, "data", StringType.get()),
+                    optional(2, "extra", StringType.get())),
+                new Schema(
+                    optional(0, "id", IntegerType.get()), optional(1, "data", StringType.get()))))
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+  }
+
+  @Test
+  void testSchemaWithMoreColumns() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(0, "id", IntegerType.get()), optional(1, "data", StringType.get())),
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(1, "data", StringType.get()),
+                    optional(2, "extra", StringType.get()))))
+        .isEqualTo(CompareSchemasVisitor.Result.DATA_CONVERSION_NEEDED);
+  }
+
+  @Test
+  void testDifferentType() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", LongType.get()), optional(2, "extra", StringType.get())),
+                new Schema(
+                    optional(1, "id", IntegerType.get()), optional(2, "extra", StringType.get()))))
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+  }
+
+  @Test
+  void testCompatibleType() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", IntegerType.get()), optional(2, "extra", StringType.get())),
+                new Schema(
+                    optional(1, "id", LongType.get()), optional(2, "extra", StringType.get()))))
+        .isEqualTo(CompareSchemasVisitor.Result.DATA_CONVERSION_NEEDED);
+  }
+
+  @Test
+  void testWithRequiredChange() {
+    Schema dataSchema =
+        new Schema(optional(1, "id", IntegerType.get()), optional(2, "extra", StringType.get()));
+    Schema tableSchema =
+        new Schema(required(1, "id", IntegerType.get()), optional(2, "extra", StringType.get()));
+    assertThat(CompareSchemasVisitor.visit(dataSchema, tableSchema))
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+    assertThat(CompareSchemasVisitor.visit(tableSchema, dataSchema))
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+  }
+
+  @Test
+  void testStructDifferentId() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(2, "struct1", StructType.of(optional(3, "extra", IntegerType.get())))),
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(
+                        1, "struct1", StructType.of(optional(2, "extra", IntegerType.get()))))))
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+  }
+
+  @Test
+  void testStructChanged() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(1, "struct1", StructType.of(optional(2, "extra", LongType.get())))),
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(
+                        2, "struct1", StructType.of(optional(3, "extra", IntegerType.get()))))))
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+  }
+
+  @Test
+  void testMapDifferentId() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(
+                        2, "map1", MapType.ofOptional(3, 4, IntegerType.get(), StringType.get()))),
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(
+                        1, "map1", MapType.ofOptional(2, 3, IntegerType.get(), StringType.get())))))
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+  }
+
+  @Test
+  void testMapChanged() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(
+                        2, "map1", MapType.ofOptional(3, 4, LongType.get(), StringType.get()))),
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(
+                        2, "map1", MapType.ofOptional(3, 4, IntegerType.get(), StringType.get())))))
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+  }
+
+  @Test
+  void testListDifferentId() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(2, "list1", ListType.ofOptional(3, IntegerType.get()))),
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(1, "list1", ListType.ofOptional(2, IntegerType.get())))))
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+  }
+
+  @Test
+  void testListChanged() {
+    assertThat(
+            CompareSchemasVisitor.visit(
+                new Schema(
+                    optional(0, "id", IntegerType.get()),
+                    optional(1, "list1", ListType.ofOptional(2, LongType.get()))),
+                new Schema(
+                    optional(1, "id", IntegerType.get()),
+                    optional(2, "list1", ListType.ofOptional(3, IntegerType.get())))))
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+  }
+}
diff --git a/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestEvolveSchemaVisitor.java b/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestEvolveSchemaVisitor.java
new file mode 100644
index 000000000000..58ee84529193
--- /dev/null
+++ b/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestEvolveSchemaVisitor.java
@@ -0,0 +1,623 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import static org.apache.iceberg.types.Types.NestedField.of;
+import static org.apache.iceberg.types.Types.NestedField.optional;
+import static org.apache.iceberg.types.Types.NestedField.required;
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.assertThatThrownBy;
+
+import java.lang.reflect.Constructor;
+import java.util.Arrays;
+import java.util.List;
+import java.util.concurrent.atomic.AtomicInteger;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.UpdateSchema;
+import org.apache.iceberg.relocated.com.google.common.collect.Lists;
+import org.apache.iceberg.types.Type.PrimitiveType;
+import org.apache.iceberg.types.Types;
+import org.apache.iceberg.types.Types.DecimalType;
+import org.apache.iceberg.types.Types.DoubleType;
+import org.apache.iceberg.types.Types.FloatType;
+import org.apache.iceberg.types.Types.IntegerType;
+import org.apache.iceberg.types.Types.ListType;
+import org.apache.iceberg.types.Types.LongType;
+import org.apache.iceberg.types.Types.MapType;
+import org.apache.iceberg.types.Types.StringType;
+import org.apache.iceberg.types.Types.StructType;
+import org.apache.iceberg.types.Types.TimeType;
+import org.apache.iceberg.types.Types.UUIDType;
+import org.junit.jupiter.api.Test;
+
+public class TestEvolveSchemaVisitor {
+
+  private static List<? extends PrimitiveType> primitiveTypes() {
+    return Lists.newArrayList(
+        StringType.get(),
+        TimeType.get(),
+        Types.TimestampType.withoutZone(),
+        Types.TimestampType.withZone(),
+        UUIDType.get(),
+        Types.DateType.get(),
+        Types.BooleanType.get(),
+        Types.BinaryType.get(),
+        DoubleType.get(),
+        IntegerType.get(),
+        Types.FixedType.ofLength(10),
+        DecimalType.of(10, 2),
+        LongType.get(),
+        FloatType.get());
+  }
+
+  private static Types.NestedField[] primitiveFields(
+      Integer initialValue, List<? extends PrimitiveType> primitiveTypes) {
+    return primitiveFields(initialValue, primitiveTypes, true);
+  }
+
+  private static Types.NestedField[] primitiveFields(
+      Integer initialValue, List<? extends PrimitiveType> primitiveTypes, boolean optional) {
+    AtomicInteger atomicInteger = new AtomicInteger(initialValue);
+    return primitiveTypes.stream()
+        .map(
+            type ->
+                of(
+                    atomicInteger.incrementAndGet(),
+                    optional,
+                    type.toString(),
+                    Types.fromPrimitiveString(type.toString())))
+        .toArray(Types.NestedField[]::new);
+  }
+
+  @Test
+  public void testAddTopLevelPrimitives() {
+    Schema targetSchema = new Schema(primitiveFields(0, primitiveTypes()));
+    UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+    EvolveSchemaVisitor.visit(updateApi, new Schema(), targetSchema);
+    assertThat(targetSchema.asStruct()).isEqualTo(updateApi.apply().asStruct());
+  }
+
+  @Test
+  public void testMakeTopLevelPrimitivesOptional() {
+    Schema existingSchema = new Schema(primitiveFields(0, primitiveTypes(), false));
+    assertThat(existingSchema.columns().stream().allMatch(Types.NestedField::isRequired)).isTrue();
+
+    UpdateSchema updateApi = loadUpdateApi(existingSchema, 0);
+    EvolveSchemaVisitor.visit(updateApi, existingSchema, new Schema());
+    Schema newSchema = updateApi.apply();
+    assertThat(newSchema.asStruct().fields().size()).isEqualTo(14);
+    assertThat(newSchema.columns().stream().allMatch(Types.NestedField::isOptional)).isTrue();
+  }
+
+  @Test
+  public void testIdentifyFieldsByName() {
+    Schema existingSchema =
+        new Schema(Types.NestedField.optional(42, "myField", Types.LongType.get()));
+    UpdateSchema updateApi = loadUpdateApi(existingSchema, 0);
+    Schema newSchema =
+        new Schema(Arrays.asList(Types.NestedField.optional(-1, "myField", Types.LongType.get())));
+    EvolveSchemaVisitor.visit(updateApi, existingSchema, newSchema);
+    assertThat(updateApi.apply().sameSchema(existingSchema)).isTrue();
+  }
+
+  @Test
+  public void testChangeOrderTopLevelPrimitives() {
+    Schema existingSchema =
+        new Schema(
+            Arrays.asList(optional(1, "a", StringType.get()), optional(2, "b", StringType.get())));
+    Schema targetSchema =
+        new Schema(
+            Arrays.asList(optional(2, "b", StringType.get()), optional(1, "a", StringType.get())));
+    UpdateSchema updateApi = loadUpdateApi(existingSchema, 0);
+    EvolveSchemaVisitor.visit(updateApi, existingSchema, targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testAddTopLevelListOfPrimitives() {
+    for (PrimitiveType primitiveType : primitiveTypes()) {
+      Schema targetSchema = new Schema(optional(1, "aList", ListType.ofOptional(2, primitiveType)));
+      UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+      EvolveSchemaVisitor.visit(updateApi, new Schema(), targetSchema);
+      assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+    }
+  }
+
+  @Test
+  public void testMakeTopLevelListOfPrimitivesOptional() {
+    for (PrimitiveType primitiveType : primitiveTypes()) {
+      Schema existingSchema =
+          new Schema(optional(1, "aList", ListType.ofRequired(2, primitiveType)));
+      Schema targetSchema = new Schema();
+      UpdateSchema updateApi = loadUpdateApi(existingSchema, 0);
+      EvolveSchemaVisitor.visit(updateApi, existingSchema, targetSchema);
+      Schema expectedSchema =
+          new Schema(optional(1, "aList", ListType.ofRequired(2, primitiveType)));
+      assertThat(updateApi.apply().asStruct()).isEqualTo(expectedSchema.asStruct());
+    }
+  }
+
+  @Test
+  public void testAddTopLevelMapOfPrimitives() {
+    for (PrimitiveType primitiveType : primitiveTypes()) {
+      Schema targetSchema =
+          new Schema(optional(1, "aMap", MapType.ofOptional(2, 3, primitiveType, primitiveType)));
+      UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+      EvolveSchemaVisitor.visit(updateApi, new Schema(), targetSchema);
+      assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+    }
+  }
+
+  @Test
+  public void testAddTopLevelStructOfPrimitives() {
+    for (PrimitiveType primitiveType : primitiveTypes()) {
+      Schema currentSchema =
+          new Schema(
+              optional(1, "aStruct", StructType.of(optional(2, "primitive", primitiveType))));
+      UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+      EvolveSchemaVisitor.visit(updateApi, new Schema(), currentSchema);
+      assertThat(updateApi.apply().asStruct()).isEqualTo(currentSchema.asStruct());
+    }
+  }
+
+  @Test
+  public void testAddNestedPrimitive() {
+    for (PrimitiveType primitiveType : primitiveTypes()) {
+      Schema currentSchema = new Schema(optional(1, "aStruct", StructType.of()));
+      Schema targetSchema =
+          new Schema(
+              optional(1, "aStruct", StructType.of(optional(2, "primitive", primitiveType))));
+      UpdateSchema updateApi = loadUpdateApi(currentSchema, 1);
+      EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+      assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+    }
+  }
+
+  @Test
+  public void testMakeNestedPrimitiveOptional() {
+    for (PrimitiveType primitiveType : primitiveTypes()) {
+      Schema currentSchema =
+          new Schema(
+              optional(1, "aStruct", StructType.of(required(2, "primitive", primitiveType))));
+      Schema targetSchema =
+          new Schema(
+              optional(1, "aStruct", StructType.of(optional(2, "primitive", primitiveType))));
+      UpdateSchema updateApi = loadUpdateApi(currentSchema, 1);
+      EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+      assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+    }
+  }
+
+  @Test
+  public void testAddNestedPrimitives() {
+    Schema currentSchema = new Schema(optional(1, "aStruct", StructType.of()));
+    Schema targetSchema =
+        new Schema(optional(1, "aStruct", StructType.of(primitiveFields(1, primitiveTypes()))));
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 1);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testAddNestedLists() {
+    Schema targetSchema =
+        new Schema(
+            optional(
+                1,
+                "aList",
+                ListType.ofOptional(
+                    2,
+                    ListType.ofOptional(
+                        3,
+                        ListType.ofOptional(
+                            4,
+                            ListType.ofOptional(
+                                5,
+                                ListType.ofOptional(
+                                    6,
+                                    ListType.ofOptional(
+                                        7,
+                                        ListType.ofOptional(
+                                            8,
+                                            ListType.ofOptional(
+                                                9,
+                                                ListType.ofOptional(
+                                                    10, DecimalType.of(11, 20))))))))))));
+    UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+    EvolveSchemaVisitor.visit(updateApi, new Schema(), targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testAddNestedStruct() {
+    Schema targetSchema =
+        new Schema(
+            optional(
+                1,
+                "struct1",
+                StructType.of(
+                    optional(
+                        2,
+                        "struct2",
+                        StructType.of(
+                            optional(
+                                3,
+                                "struct3",
+                                StructType.of(
+                                    optional(
+                                        4,
+                                        "struct4",
+                                        StructType.of(
+                                            optional(
+                                                5,
+                                                "struct5",
+                                                StructType.of(
+                                                    optional(
+                                                        6,
+                                                        "struct6",
+                                                        StructType.of(
+                                                            optional(
+                                                                7,
+                                                                "aString",
+                                                                StringType.get()))))))))))))));
+    UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+    EvolveSchemaVisitor.visit(updateApi, new Schema(), targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testAddNestedMaps() {
+    Schema targetSchema =
+        new Schema(
+            optional(
+                1,
+                "struct",
+                MapType.ofOptional(
+                    2,
+                    3,
+                    StringType.get(),
+                    MapType.ofOptional(
+                        4,
+                        5,
+                        StringType.get(),
+                        MapType.ofOptional(
+                            6,
+                            7,
+                            StringType.get(),
+                            MapType.ofOptional(
+                                8,
+                                9,
+                                StringType.get(),
+                                MapType.ofOptional(
+                                    10,
+                                    11,
+                                    StringType.get(),
+                                    MapType.ofOptional(
+                                        12, 13, StringType.get(), StringType.get()))))))));
+    UpdateSchema updateApi = loadUpdateApi(new Schema(), 0);
+    EvolveSchemaVisitor.visit(updateApi, new Schema(), targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testDetectInvalidTopLevelList() {
+    Schema currentSchema =
+        new Schema(optional(1, "aList", ListType.ofOptional(2, StringType.get())));
+    Schema targetSchema = new Schema(optional(1, "aList", ListType.ofOptional(2, LongType.get())));
+    assertThatThrownBy(
+            () ->
+                EvolveSchemaVisitor.visit(
+                    loadUpdateApi(currentSchema, 2), currentSchema, targetSchema))
+        .hasMessage("Cannot change column type: aList.element: string -> long")
+        .isInstanceOf(IllegalArgumentException.class);
+  }
+
+  @Test
+  public void testDetectInvalidTopLevelMapValue() {
+
+    Schema currentSchema =
+        new Schema(
+            optional(1, "aMap", MapType.ofOptional(2, 3, StringType.get(), StringType.get())));
+    Schema targetSchema =
+        new Schema(optional(1, "aMap", MapType.ofOptional(2, 3, StringType.get(), LongType.get())));
+
+    assertThatThrownBy(
+            () ->
+                EvolveSchemaVisitor.visit(
+                    loadUpdateApi(currentSchema, 3), currentSchema, targetSchema))
+        .hasMessage("Cannot change column type: aMap.value: string -> long")
+        .isInstanceOf(IllegalArgumentException.class);
+  }
+
+  @Test
+  public void testDetectInvalidTopLevelMapKey() {
+    Schema currentSchema =
+        new Schema(
+            optional(1, "aMap", MapType.ofOptional(2, 3, StringType.get(), StringType.get())));
+    Schema targetSchema =
+        new Schema(optional(1, "aMap", MapType.ofOptional(2, 3, UUIDType.get(), StringType.get())));
+    assertThatThrownBy(
+            () ->
+                EvolveSchemaVisitor.visit(
+                    loadUpdateApi(currentSchema, 3), currentSchema, targetSchema))
+        .hasMessage("Cannot change column type: aMap.key: string -> uuid")
+        .isInstanceOf(IllegalArgumentException.class);
+  }
+
+  @Test
+  // int 32-bit signed integers -> Can promote to long
+  public void testTypePromoteIntegerToLong() {
+    Schema currentSchema = new Schema(required(1, "aCol", IntegerType.get()));
+    Schema targetSchema = new Schema(required(1, "aCol", LongType.get()));
+
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 0);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    Schema applied = updateApi.apply();
+    assertThat(applied.asStruct().fields().size()).isEqualTo(1);
+    assertThat(applied.asStruct().fields().get(0).type()).isEqualTo(LongType.get());
+  }
+
+  @Test
+  // float 32-bit IEEE 754 floating point -> Can promote to double
+  public void testTypePromoteFloatToDouble() {
+    Schema currentSchema = new Schema(required(1, "aCol", FloatType.get()));
+    Schema targetSchema = new Schema(required(1, "aCol", DoubleType.get()));
+
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 0);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    Schema applied = updateApi.apply();
+    assertThat(applied.asStruct().fields().size()).isEqualTo(1);
+    assertThat(applied.asStruct().fields().get(0).type()).isEqualTo(DoubleType.get());
+  }
+
+  @Test
+  public void testInvalidTypePromoteDoubleToFloat() {
+    Schema currentSchema = new Schema(required(1, "aCol", DoubleType.get()));
+    Schema targetSchema = new Schema(required(1, "aCol", FloatType.get()));
+    assertThatThrownBy(
+            () ->
+                EvolveSchemaVisitor.visit(
+                    loadUpdateApi(currentSchema, 3), currentSchema, targetSchema))
+        .hasMessage("Cannot change column type: aCol: double -> float")
+        .isInstanceOf(IllegalArgumentException.class);
+  }
+
+  @Test
+  // decimal(P,S) Fixed-point decimal; precision P, scale S -> Scale is fixed [1], precision must be
+  // 38 or less
+  public void testTypePromoteDecimalToFixedScaleWithWiderPrecision() {
+    Schema currentSchema = new Schema(required(1, "aCol", DecimalType.of(20, 1)));
+    Schema targetSchema = new Schema(required(1, "aCol", DecimalType.of(22, 1)));
+
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 1);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testAddPrimitiveToNestedStruct() {
+    Schema existingSchema =
+        new Schema(
+            required(
+                1,
+                "struct1",
+                StructType.of(
+                    optional(
+                        2,
+                        "struct2",
+                        StructType.of(
+                            optional(
+                                3,
+                                "list",
+                                ListType.ofOptional(
+                                    4,
+                                    StructType.of(optional(5, "number", IntegerType.get())))))))));
+
+    Schema targetSchema =
+        new Schema(
+            required(
+                1,
+                "struct1",
+                StructType.of(
+                    optional(
+                        2,
+                        "struct2",
+                        StructType.of(
+                            optional(
+                                3,
+                                "list",
+                                ListType.ofOptional(
+                                    4,
+                                    StructType.of(
+                                        optional(5, "number", LongType.get()),
+                                        optional(6, "time", TimeType.get())))))))));
+
+    UpdateSchema updateApi = loadUpdateApi(existingSchema, 5);
+    EvolveSchemaVisitor.visit(updateApi, existingSchema, targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testReplaceListWithPrimitive() {
+    Schema currentSchema =
+        new Schema(optional(1, "aColumn", ListType.ofOptional(2, StringType.get())));
+    Schema targetSchema = new Schema(optional(1, "aColumn", StringType.get()));
+    assertThatThrownBy(
+            () ->
+                EvolveSchemaVisitor.visit(
+                    loadUpdateApi(currentSchema, 3), currentSchema, targetSchema))
+        .hasMessage("Cannot change column type: aColumn: list<string> -> string")
+        .isInstanceOf(IllegalArgumentException.class);
+  }
+
+  @Test
+  public void addNewTopLevelStruct() {
+    Schema currentSchema =
+        new Schema(
+            optional(
+                1,
+                "map1",
+                MapType.ofOptional(
+                    2,
+                    3,
+                    StringType.get(),
+                    ListType.ofOptional(
+                        4, StructType.of(optional(5, "string1", StringType.get()))))));
+
+    Schema targetSchema =
+        new Schema(
+            optional(
+                1,
+                "map1",
+                MapType.ofOptional(
+                    2,
+                    3,
+                    StringType.get(),
+                    ListType.ofOptional(
+                        4, StructType.of(optional(5, "string1", StringType.get()))))),
+            optional(
+                6,
+                "struct1",
+                StructType.of(
+                    optional(7, "d1", StructType.of(optional(8, "d2", StringType.get()))))));
+
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 5);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testAppendNestedStruct() {
+    Schema currentSchema =
+        new Schema(
+            required(
+                1,
+                "s1",
+                StructType.of(
+                    optional(
+                        2,
+                        "s2",
+                        StructType.of(
+                            optional(
+                                3, "s3", StructType.of(optional(4, "s4", StringType.get()))))))));
+
+    Schema targetSchema =
+        new Schema(
+            required(
+                1,
+                "s1",
+                StructType.of(
+                    optional(
+                        2,
+                        "s2",
+                        StructType.of(
+                            optional(3, "s3", StructType.of(optional(4, "s4", StringType.get()))),
+                            optional(
+                                5,
+                                "repeat",
+                                StructType.of(
+                                    optional(
+                                        6,
+                                        "s1",
+                                        StructType.of(
+                                            optional(
+                                                7,
+                                                "s2",
+                                                StructType.of(
+                                                    optional(
+                                                        8,
+                                                        "s3",
+                                                        StructType.of(
+                                                            optional(
+                                                                9,
+                                                                "s4",
+                                                                StringType.get()))))))))))))));
+
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 4);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    assertThat(updateApi.apply().asStruct()).isEqualTo(targetSchema.asStruct());
+  }
+
+  @Test
+  public void testMakeNestedStructOptional() {
+    Schema currentSchema = getNestedSchemaWithOptionalModifier(false);
+    Schema targetSchema =
+        new Schema(
+            required(
+                1,
+                "s1",
+                StructType.of(
+                    optional(
+                        2,
+                        "s2",
+                        StructType.of(
+                            optional(
+                                3, "s3", StructType.of(optional(4, "s4", StringType.get()))))))));
+    UpdateSchema updateApi = loadUpdateApi(currentSchema, 9);
+    EvolveSchemaVisitor.visit(updateApi, currentSchema, targetSchema);
+    assertThat(getNestedSchemaWithOptionalModifier(true).asStruct())
+        .isEqualTo(updateApi.apply().asStruct());
+  }
+
+  private static Schema getNestedSchemaWithOptionalModifier(boolean nestedIsOptional) {
+    return new Schema(
+        required(
+            1,
+            "s1",
+            StructType.of(
+                optional(
+                    2,
+                    "s2",
+                    StructType.of(
+                        optional(3, "s3", StructType.of(optional(4, "s4", StringType.get()))),
+                        of(
+                            5,
+                            nestedIsOptional,
+                            "repeat",
+                            StructType.of(
+                                optional(
+                                    6,
+                                    "s1",
+                                    StructType.of(
+                                        optional(
+                                            7,
+                                            "s2",
+                                            StructType.of(
+                                                optional(
+                                                    8,
+                                                    "s3",
+                                                    StructType.of(
+                                                        optional(
+                                                            9, "s4", StringType.get()))))))))))))));
+  }
+
+  private static UpdateSchema loadUpdateApi(Schema schema, int lastColumnId) {
+    try {
+      Constructor<?> constructor =
+          TestEvolveSchemaVisitor.class
+              .getClassLoader()
+              .loadClass("org.apache.iceberg.SchemaUpdate")
+              .getDeclaredConstructor(Schema.class, int.class);
+      constructor.setAccessible(true);
+      return (UpdateSchema) constructor.newInstance(schema, lastColumnId);
+    } catch (Exception e) {
+      throw new RuntimeException("Failed to instantiate SchemaUpdate class", e);
+    }
+  }
+}
diff --git a/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestPartitionSpecEvolution.java b/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestPartitionSpecEvolution.java
new file mode 100644
index 000000000000..3e7025de6f91
--- /dev/null
+++ b/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestPartitionSpecEvolution.java
@@ -0,0 +1,188 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+import org.apache.iceberg.PartitionSpec;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.types.Types;
+import org.junit.jupiter.api.Test;
+
+public class TestPartitionSpecEvolution {
+
+  @Test
+  void testCompatible() {
+    Schema schema =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema).bucket("id", 10).build();
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema).bucket("id", 10).build();
+
+    // Happy case, source ids and names match
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isTrue();
+  }
+
+  @Test
+  void testNotCompatibleDifferentTransform() {
+    Schema schema =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema).bucket("id", 10).build();
+    // Same spec als spec1 but different number of buckets
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema).bucket("id", 23).build();
+
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isFalse();
+  }
+
+  @Test
+  void testNotCompatibleMoreFields() {
+    Schema schema =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema).bucket("id", 10).build();
+    // Additional field
+    PartitionSpec spec2 =
+        PartitionSpec.builderFor(schema).bucket("id", 10).truncate("data", 1).build();
+
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isFalse();
+  }
+
+  @Test
+  void testCompatibleWithNonMatchingSourceIds() {
+    Schema schema1 =
+        new Schema(
+            // Use zero-based field ids
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema1).bucket("id", 10).build();
+
+    Schema schema2 =
+        new Schema(
+            Types.NestedField.required(1, "id", Types.IntegerType.get()),
+            Types.NestedField.required(2, "data", Types.StringType.get()));
+
+    // Same spec als spec1 but bound to a different schema
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema2).bucket("id", 10).build();
+
+    // Compatible because the source names match
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isTrue();
+  }
+
+  @Test
+  void testPartitionSpecEvolution() {
+    Schema schema1 =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema1).bucket("id", 10).build();
+
+    Schema schema2 =
+        new Schema(
+            Types.NestedField.required(1, "id", Types.IntegerType.get()),
+            Types.NestedField.required(2, "data", Types.StringType.get()));
+
+    // Change num buckets
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema2).bucket("id", 23).build();
+
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isFalse();
+    PartitionSpecEvolution.PartitionSpecChanges result =
+        PartitionSpecEvolution.evolve(spec1, spec2);
+
+    assertThat(result.termsToAdd().toString()).isEqualTo("[bucket[23](ref(name=\"id\"))]");
+    assertThat(result.termsToRemove().toString()).isEqualTo("[bucket[10](ref(name=\"id\"))]");
+  }
+
+  @Test
+  void testPartitionSpecEvolutionAddField() {
+    Schema schema =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema).build();
+    // Add field
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema).bucket("id", 23).build();
+
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isFalse();
+    PartitionSpecEvolution.PartitionSpecChanges result =
+        PartitionSpecEvolution.evolve(spec1, spec2);
+
+    assertThat(result.termsToAdd().toString()).isEqualTo("[bucket[23](ref(name=\"id\"))]");
+    assertThat(result.termsToRemove().toString()).isEqualTo("[]");
+  }
+
+  @Test
+  void testPartitionSpecEvolutionRemoveField() {
+    Schema schema =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(1, "data", Types.StringType.get()));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema).bucket("id", 23).build();
+    // Remove field
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema).build();
+
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isFalse();
+    PartitionSpecEvolution.PartitionSpecChanges result =
+        PartitionSpecEvolution.evolve(spec1, spec2);
+
+    assertThat(result.termsToAdd().toString()).isEqualTo("[]");
+    assertThat(result.termsToRemove().toString()).isEqualTo("[bucket[23](ref(name=\"id\"))]");
+  }
+
+  @Test
+  void testPartitionSpecEvolutionWithNestedFields() {
+    Schema schema1 =
+        new Schema(
+            Types.NestedField.required(0, "id", Types.IntegerType.get()),
+            Types.NestedField.required(
+                1,
+                "data",
+                Types.StructType.of(Types.NestedField.required(2, "str", Types.StringType.get()))));
+
+    PartitionSpec spec1 = PartitionSpec.builderFor(schema1).bucket("data.str", 10).build();
+
+    Schema schema2 =
+        new Schema(
+            Types.NestedField.required(1, "id", Types.IntegerType.get()),
+            Types.NestedField.required(
+                2,
+                "data",
+                Types.StructType.of(Types.NestedField.required(3, "str", Types.StringType.get()))));
+
+    // Change num buckets
+    PartitionSpec spec2 = PartitionSpec.builderFor(schema2).bucket("data.str", 23).build();
+
+    assertThat(PartitionSpecEvolution.checkCompatibility(spec1, spec2)).isFalse();
+    PartitionSpecEvolution.PartitionSpecChanges result =
+        PartitionSpecEvolution.evolve(spec1, spec2);
+
+    assertThat(result.termsToAdd().toString()).isEqualTo("[bucket[23](ref(name=\"data.str\"))]");
+    assertThat(result.termsToRemove().toString()).isEqualTo("[bucket[10](ref(name=\"data.str\"))]");
+  }
+}
diff --git a/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestTableMetadataCache.java b/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestTableMetadataCache.java
new file mode 100644
index 000000000000..cedae887041e
--- /dev/null
+++ b/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestTableMetadataCache.java
@@ -0,0 +1,94 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+import org.apache.commons.lang3.SerializationUtils;
+import org.apache.iceberg.PartitionSpec;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.catalog.Catalog;
+import org.apache.iceberg.catalog.TableIdentifier;
+import org.apache.iceberg.flink.sink.TestFlinkIcebergSinkBase;
+import org.apache.iceberg.types.Types;
+import org.junit.jupiter.api.Test;
+
+public class TestTableMetadataCache extends TestFlinkIcebergSinkBase {
+
+  static final Schema SCHEMA =
+      new Schema(
+          Types.NestedField.optional(1, "id", Types.IntegerType.get()),
+          Types.NestedField.optional(2, "data", Types.StringType.get()));
+
+  static final Schema SCHEMA2 =
+      new Schema(
+          Types.NestedField.optional(1, "id", Types.IntegerType.get()),
+          Types.NestedField.optional(2, "data", Types.StringType.get()),
+          Types.NestedField.optional(3, "extra", Types.StringType.get()));
+
+  @Test
+  void testCaching() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("default.myTable");
+    catalog.createTable(tableIdentifier, SCHEMA);
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+
+    Schema schema1 = cache.schema(tableIdentifier, SCHEMA).f0;
+    assertThat(schema1.sameSchema(SCHEMA)).isTrue();
+    assertThat(cache.schema(tableIdentifier, SerializationUtils.clone(SCHEMA)).f0)
+        .isEqualTo(schema1);
+
+    assertThat(cache.schema(tableIdentifier, SCHEMA2)).isEqualTo(TableMetadataCache.NOT_FOUND);
+
+    schema1 = cache.schema(tableIdentifier, SCHEMA).f0;
+    assertThat(cache.schema(tableIdentifier, SerializationUtils.clone(SCHEMA)).f0)
+        .isEqualTo(schema1);
+  }
+
+  @Test
+  void testCacheInvalidationAfterSchemaChange() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("default.myTable");
+    catalog.createTable(tableIdentifier, SCHEMA);
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    Schema schema1 = cache.schema(tableIdentifier, SCHEMA).f0;
+    assertThat(schema1.sameSchema(SCHEMA)).isTrue();
+
+    catalog.dropTable(tableIdentifier);
+    catalog.createTable(tableIdentifier, SCHEMA2);
+    tableUpdater.update(tableIdentifier, "main", SCHEMA2, PartitionSpec.unpartitioned());
+
+    Schema schema2 = cache.schema(tableIdentifier, SCHEMA2).f0;
+    assertThat(schema2.sameSchema(SCHEMA2)).isTrue();
+  }
+
+  @Test
+  void testCachingDisabled() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("default.myTable");
+    catalog.createTable(tableIdentifier, SCHEMA);
+    TableMetadataCache cache = new TableMetadataCache(catalog, 0, Long.MAX_VALUE);
+
+    // Cleanup routine doesn't run after every write
+    cache.getInternalCache().cleanUp();
+    assertThat(cache.getInternalCache().estimatedSize()).isEqualTo(0);
+  }
+}
diff --git a/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestTableUpdater.java b/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestTableUpdater.java
new file mode 100644
index 000000000000..f7a3596462f1
--- /dev/null
+++ b/flink/v1.20/flink/src/test/java/org/apache/iceberg/flink/sink/dynamic/TestTableUpdater.java
@@ -0,0 +1,160 @@
+/*
+ * Licensed to the Apache Software Foundation (ASF) under one
+ * or more contributor license agreements.  See the NOTICE file
+ * distributed with this work for additional information
+ * regarding copyright ownership.  The ASF licenses this file
+ * to you under the Apache License, Version 2.0 (the
+ * "License"); you may not use this file except in compliance
+ * with the License.  You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing,
+ * software distributed under the License is distributed on an
+ * "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+ * KIND, either express or implied.  See the License for the
+ * specific language governing permissions and limitations
+ * under the License.
+ */
+package org.apache.iceberg.flink.sink.dynamic;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+import org.apache.flink.api.java.tuple.Tuple2;
+import org.apache.flink.api.java.tuple.Tuple3;
+import org.apache.iceberg.PartitionSpec;
+import org.apache.iceberg.Schema;
+import org.apache.iceberg.Table;
+import org.apache.iceberg.catalog.Catalog;
+import org.apache.iceberg.catalog.TableIdentifier;
+import org.apache.iceberg.flink.sink.TestFlinkIcebergSinkBase;
+import org.apache.iceberg.types.Types;
+import org.junit.jupiter.api.Test;
+
+public class TestTableUpdater extends TestFlinkIcebergSinkBase {
+
+  static final Schema SCHEMA =
+      new Schema(
+          Types.NestedField.optional(1, "id", Types.IntegerType.get()),
+          Types.NestedField.optional(2, "data", Types.StringType.get()));
+
+  static final Schema SCHEMA2 =
+      new Schema(
+          Types.NestedField.optional(1, "id", Types.IntegerType.get()),
+          Types.NestedField.optional(2, "data", Types.StringType.get()),
+          Types.NestedField.optional(3, "extra", Types.StringType.get()));
+
+  @Test
+  void testTableCreation() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("myTable");
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    tableUpdater.update(tableIdentifier, "main", SCHEMA, PartitionSpec.unpartitioned());
+    assertThat(catalog.tableExists(tableIdentifier)).isTrue();
+
+    Tuple2<Schema, CompareSchemasVisitor.Result> cachedSchema =
+        cache.schema(tableIdentifier, SCHEMA);
+    assertThat(cachedSchema.f0.sameSchema(SCHEMA)).isTrue();
+  }
+
+  @Test
+  void testTableAlreadyExists() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("myTable");
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    // Make the table non-existent in cache
+    cache.exists(tableIdentifier);
+    // Create the table
+    catalog.createTable(tableIdentifier, SCHEMA);
+    // Make sure that the cache is invalidated and the table refreshed without an error
+    Tuple3<Schema, CompareSchemasVisitor.Result, PartitionSpec> result =
+        tableUpdater.update(tableIdentifier, "main", SCHEMA, PartitionSpec.unpartitioned());
+    assertThat(result.f0.sameSchema(SCHEMA)).isTrue();
+    assertThat(result.f1).isEqualTo(CompareSchemasVisitor.Result.SAME);
+    assertThat(result.f2).isEqualTo(PartitionSpec.unpartitioned());
+  }
+
+  @Test
+  void testBranchCreationAndCaching() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("myTable");
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    catalog.createTable(tableIdentifier, SCHEMA);
+    tableUpdater.update(tableIdentifier, "myBranch", SCHEMA, PartitionSpec.unpartitioned());
+    TableMetadataCache.CacheItem cacheItem = cache.getInternalCache().getIfPresent(tableIdentifier);
+    assertThat(cacheItem).isNotNull();
+
+    tableUpdater.update(tableIdentifier, "myBranch", SCHEMA, PartitionSpec.unpartitioned());
+    assertThat(cache.getInternalCache().getIfPresent(tableIdentifier)).isEqualTo(cacheItem);
+  }
+
+  @Test
+  void testSpecCreation() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("myTable");
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    PartitionSpec spec = PartitionSpec.builderFor(SCHEMA).bucket("data", 10).build();
+    Tuple3<Schema, CompareSchemasVisitor.Result, PartitionSpec> result =
+        tableUpdater.update(tableIdentifier, "main", SCHEMA, spec);
+
+    Table table = catalog.loadTable(tableIdentifier);
+    assertThat(table).isNotNull();
+    assertThat(table.spec()).isEqualTo(spec);
+  }
+
+  @Test
+  void testInvalidateOldCacheEntryOnUpdate() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("default.myTable");
+    catalog.createTable(tableIdentifier, SCHEMA);
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    cache.schema(tableIdentifier, SCHEMA);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    Schema updated =
+        tableUpdater.update(tableIdentifier, "main", SCHEMA2, PartitionSpec.unpartitioned()).f0;
+    assertThat(updated.sameSchema(SCHEMA2));
+    assertThat(cache.schema(tableIdentifier, SCHEMA2).f0.sameSchema(SCHEMA2)).isTrue();
+  }
+
+  @Test
+  void testLastResultInvalidation() {
+    Catalog catalog = CATALOG_EXTENSION.catalog();
+    TableIdentifier tableIdentifier = TableIdentifier.parse("default.myTable");
+    catalog.createTable(tableIdentifier, SCHEMA);
+    TableMetadataCache cache = new TableMetadataCache(catalog, 10, Long.MAX_VALUE);
+    TableUpdater tableUpdater = new TableUpdater(cache, catalog);
+
+    // Initialize cache
+    tableUpdater.update(tableIdentifier, "main", SCHEMA, PartitionSpec.unpartitioned());
+
+    // Update table behind the scenes
+    catalog.dropTable(tableIdentifier);
+    catalog.createTable(tableIdentifier, SCHEMA2);
+
+    // Cache still stores the old information
+    assertThat(cache.schema(tableIdentifier, SCHEMA2).f1)
+        .isEqualTo(CompareSchemasVisitor.Result.SCHEMA_UPDATE_NEEDED);
+
+    assertThat(
+            tableUpdater.update(tableIdentifier, "main", SCHEMA2, PartitionSpec.unpartitioned()).f1)
+        .isEqualTo(CompareSchemasVisitor.Result.SAME);
+
+    // Last result cache should be cleared
+    assertThat(
+            cache
+                .getInternalCache()
+                .getIfPresent(tableIdentifier)
+                .getSchemaInfo()
+                .getLastResult(SCHEMA2))
+        .isNull();
+  }
+}