diff --git a/airflow-core/src/airflow/serialization/helpers.py b/airflow-core/src/airflow/serialization/helpers.py
index 723c113709a87..021bf35f73d7c 100644
--- a/airflow-core/src/airflow/serialization/helpers.py
+++ b/airflow-core/src/airflow/serialization/helpers.py
@@ -29,6 +29,36 @@
     from airflow.timetables.base import Timetable as CoreTimetable
 
 
+def _truncate_rendered_value(rendered: str, max_length: int) -> str:
+    if max_length <= 0:
+        return ""
+
+    prefix = (
+        "Truncated. You can change this behaviour in "
+        "[core]max_templated_field_length. "
+    )
+    suffix = "..."
+    value = str(rendered)
+
+    trunc_only = f"{prefix}{suffix}"
+
+    if max_length < len(trunc_only):
+        return trunc_only
+
+    overhead = len(prefix) + 2 + len(suffix)
+    available = max_length - overhead
+
+    if available <= 0:
+        return trunc_only
+
+    return f"{prefix}'{value[:available]}'{suffix}"
+
+
+
+def _safe_truncate_rendered_value(rendered: Any, max_length: int) -> str:
+    return _truncate_rendered_value(str(rendered), max_length)
+
+
 def serialize_template_field(template_field: Any, name: str) -> str | dict | list | int | float:
     """
     Return a serializable representation of the templated field.
@@ -74,10 +104,7 @@ def sort_dict_recursively(obj: Any) -> Any:
             serialized = str(template_field)
         if len(serialized) > max_length:
             rendered = redact(serialized, name)
-            return (
-                "Truncated. You can change this behaviour in [core]max_templated_field_length. "
-                f"{rendered[: max_length - 79]!r}... "
-            )
+            return _safe_truncate_rendered_value(rendered, max_length)
         return serialized
     if not template_field and not isinstance(template_field, tuple):
         # Avoid unnecessary serialization steps for empty fields unless they are tuples
@@ -91,10 +118,7 @@ def sort_dict_recursively(obj: Any) -> Any:
     serialized = str(template_field)
     if len(serialized) > max_length:
         rendered = redact(serialized, name)
-        return (
-            "Truncated. You can change this behaviour in [core]max_templated_field_length. "
-            f"{rendered[: max_length - 79]!r}... "
-        )
+        return _safe_truncate_rendered_value(rendered, max_length)
     return template_field
 
 
diff --git a/airflow-core/tests/unit/serialization/test_helpers.py b/airflow-core/tests/unit/serialization/test_helpers.py
new file mode 100644
index 0000000000000..27111dc7e7dbf
--- /dev/null
+++ b/airflow-core/tests/unit/serialization/test_helpers.py
@@ -0,0 +1,28 @@
+# 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.
+from __future__ import annotations
+
+
+def test_serialize_template_field_with_very_small_max_length(monkeypatch):
+    monkeypatch.setenv("AIRFLOW__CORE__MAX_TEMPLATED_FIELD_LENGTH", "1")
+
+    from airflow.serialization.helpers import serialize_template_field
+
+    result = serialize_template_field("This is a long string", "test")
+
+    assert result
+    assert len(result) <= 1
diff --git a/task-sdk/src/airflow/sdk/execution_time/task_runner.py b/task-sdk/src/airflow/sdk/execution_time/task_runner.py
index 85fd83551d4d8..95e213afa745b 100644
--- a/task-sdk/src/airflow/sdk/execution_time/task_runner.py
+++ b/task-sdk/src/airflow/sdk/execution_time/task_runner.py
@@ -826,6 +826,32 @@ def startup() -> tuple[RuntimeTaskInstance, Context, Logger]:
 
     return ti, ti.get_template_context(), log
 
+def _truncate_rendered_value(rendered: str, max_length: int) -> str:
+    if max_length <= 0:
+        return ""
+
+    prefix = (
+        "Truncated. You can change this behaviour in "
+        "[core]max_templated_field_length. "
+    )
+    suffix = "..."
+    value = str(rendered)
+
+    trunc_only = f"{prefix}{suffix}"
+
+    if max_length < len(trunc_only):
+        return trunc_only
+
+    overhead = len(prefix) + 2 + len(suffix)
+    available = max_length - overhead
+
+    if available <= 0:
+        return trunc_only
+
+    return f"{prefix}'{value[:available]}'{suffix}"
+def _safe_truncate_rendered_value(rendered: Any, max_length: int) -> str:
+    return _truncate_rendered_value(str(rendered), max_length)
+
 
 def _serialize_template_field(template_field: Any, name: str) -> str | dict | list | int | float:
     """
@@ -877,10 +903,7 @@ def sort_dict_recursively(obj: Any) -> Any:
             serialized = str(template_field)
         if len(serialized) > max_length:
             rendered = redact(serialized, name)
-            return (
-                "Truncated. You can change this behaviour in [core]max_templated_field_length. "
-                f"{rendered[: max_length - 79]!r}... "
-            )
+            return _safe_truncate_rendered_value(rendered, max_length)
         return serialized
     if not template_field and not isinstance(template_field, tuple):
         # Avoid unnecessary serialization steps for empty fields unless they are tuples
@@ -894,10 +917,7 @@ def sort_dict_recursively(obj: Any) -> Any:
     serialized = str(template_field)
     if len(serialized) > max_length:
         rendered = redact(serialized, name)
-        return (
-            "Truncated. You can change this behaviour in [core]max_templated_field_length. "
-            f"{rendered[: max_length - 79]!r}... "
-        )
+        return _safe_truncate_rendered_value(rendered, max_length)
     return template_field