diff --git a/Sources/CodableDatastore/Persistence/Disk Persistence/Datastore/DatastoreIndex.swift b/Sources/CodableDatastore/Persistence/Disk Persistence/Datastore/DatastoreIndex.swift
index f575551..4ee7944 100644
--- a/Sources/CodableDatastore/Persistence/Disk Persistence/Datastore/DatastoreIndex.swift	
+++ b/Sources/CodableDatastore/Persistence/Disk Persistence/Datastore/DatastoreIndex.swift	
@@ -580,7 +580,7 @@ extension DiskPersistence.Datastore.Index {
         
         var bytesForEntry: Bytes?
         var isEntryComplete = false
-        var previousBlock: DiskPersistence.CursorBlock? = nil
+        var previousCompleteBlock: DiskPersistence.CursorBlock? = nil
         var currentBlock: DiskPersistence.CursorBlock? = nil
         var pageIndex = startingPageIndex
         
@@ -613,8 +613,15 @@ extension DiskPersistence.Datastore.Index {
                     /// In the final position, lets save and continue.
                     bytesForEntry?.append(contentsOf: bytes)
                 case .tail(let bytes):
-                    /// In the first position, lets skip it.
-                    guard bytesForEntry != nil else { continue }
+                    /// In the first position, lets skip it, but add it as the last complete block in case the next one is a step too far.
+                    guard bytesForEntry != nil else {
+                        previousCompleteBlock = DiskPersistence.CursorBlock(
+                            pageIndex: pageIndex,
+                            page: page,
+                            blockIndex: blockIndex
+                        )
+                        continue
+                    }
                     /// In the final position, lets save and stop.
                     bytesForEntry?.append(contentsOf: bytes)
                     isEntryComplete = true
@@ -625,7 +632,14 @@ extension DiskPersistence.Datastore.Index {
                     page: page,
                     blockIndex: blockIndex
                 )
-                defer { previousBlock = currentBlock }
+                
+                /// Make sure to only keep a reference to the end of the last complete block, so if we roll back, we'll have a valid cursor
+                defer {
+                    switch block {
+                    case .complete, .tail: previousCompleteBlock = currentBlock
+                    case .head, .slice: break
+                    }
+                }
                 
                 if let bytes = bytesForEntry, isEntryComplete {
                     let entry = try DatastorePageEntry(bytes: bytes, isPartial: false)
@@ -643,7 +657,7 @@ extension DiskPersistence.Datastore.Index {
                             persistence: datastore.snapshot.persistence,
                             datastore: datastore,
                             index: self,
-                            insertAfter: previousBlock
+                            insertAfter: previousCompleteBlock
                         )
                     }
                     
@@ -658,7 +672,7 @@ extension DiskPersistence.Datastore.Index {
             persistence: datastore.snapshot.persistence,
             datastore: datastore,
             index: self,
-            insertAfter: previousBlock
+            insertAfter: previousCompleteBlock
         )
     }
 }
diff --git a/Tests/CodableDatastoreTests/DiskPersistenceDatastoreIndexTests.swift b/Tests/CodableDatastoreTests/DiskPersistenceDatastoreIndexTests.swift
index 2dbb4dd..effb454 100644
--- a/Tests/CodableDatastoreTests/DiskPersistenceDatastoreIndexTests.swift
+++ b/Tests/CodableDatastoreTests/DiskPersistenceDatastoreIndexTests.swift
@@ -73,6 +73,66 @@ final class DiskPersistenceDatastoreIndexTests: XCTestCase {
         XCTAssertEqual(result, expectedIndex, file: file, line: line)
     }
     
+    func assertInsertionCursor(
+        proposedEntry: UInt8,
+        pages: [[DatastorePageEntryBlock]],
+        pageIndex: Int?,
+        blockIndex: Int?,
+        file: StaticString = #filePath,
+        line: UInt = #line
+    ) async throws {
+        let persistence = DiskPersistence(readOnlyURL: temporaryStoreURL)
+        let snapshot = Snapshot(
+            id: .init(rawValue: "Snapshot"),
+            persistence: persistence
+        )
+        let datastore = DiskPersistence.Datastore(
+            id: .init(rawValue: "Datastore"),
+            snapshot: snapshot
+        )
+        let index = DiskPersistence.Datastore.Index(
+            datastore: datastore,
+            id: .primary(manifest: .init(rawValue: "Index")),
+            manifest: DatastoreIndexManifest(
+                id: .init(rawValue: "Index"),
+                orderedPages: pages.enumerated().map { (index, _) in
+                        .existing(.init(rawValue: "Page \(index)"))
+                }
+            )
+        )
+        
+        var pageLookup: [DatastorePageIdentifier : DiskPersistence<ReadOnly>.Datastore.Page] = [:]
+        var pageInfos: [DatastoreIndexManifest.PageInfo] = []
+        
+        for (index, blocks) in pages.enumerated() {
+            let pageID = DatastorePageIdentifier(rawValue: "Page \(index)")
+            let page = DiskPersistence<ReadOnly>.Datastore.Page(
+                datastore: datastore,
+                id: .init(
+                    index: .primary(manifest: .init(rawValue: "Index")),
+                    page: pageID
+                ),
+                blocks: blocks
+            )
+            pageLookup[pageID] = page
+            pageInfos.append(.existing(pageID))
+        }
+        
+        let result = try await index.insertionCursor(for: RangeBoundExpression.including(proposedEntry), in: pageInfos) { pageID in
+            pageLookup[pageID]!
+        } comparator: { lhs, rhs in
+            lhs.sortOrder(comparedTo: rhs.headers[0][0], order: .ascending)
+        }
+        
+        XCTAssertTrue(result.persistence === persistence, file: file, line: line)
+        XCTAssertTrue(result.datastore === datastore, file: file, line: line)
+        XCTAssertEqual(result.index, index, file: file, line: line)
+        XCTAssertEqual(result.insertAfter?.pageIndex, pageIndex, file: file, line: line)
+        let pageID = await result.insertAfter?.page.id.page
+        XCTAssertEqual(pageID, pageIndex.map({ DatastorePageIdentifier(rawValue: "Page \($0)") }), file: file, line: line)
+        XCTAssertEqual(result.insertAfter?.blockIndex, blockIndex, file: file, line: line)
+    }
+    
     func testEmptyPagesSearch() async throws {
         try await assertPageSearch(proposedEntry: 0, pages: [], expectedIndex: nil)
         try await assertPageSearch(proposedEntry: 0, pages: [], expectedIndex: nil)
@@ -330,4 +390,24 @@ final class DiskPersistenceDatastoreIndexTests: XCTestCase {
             wait(for: [exp], timeout: 200.0)
         }
     }
+    
+    func testNonContiguousInsertionCursor() async throws {
+        let entry1 = DatastorePageEntry(headers: [[1]], content: [1]).blocks(remainingPageSpace: 1024, maxPageSpace: 1024)
+        let entry2 = DatastorePageEntry(headers: [[2]], content: [2]).blocks(remainingPageSpace: 1024, maxPageSpace: 1024)
+        let entry3 = DatastorePageEntry(headers: [[3]], content: Array(repeating: 3, count: 100)).blocks(remainingPageSpace: 20, maxPageSpace: 60)
+        let entry4 = DatastorePageEntry(headers: [[4]], content: [4]).blocks(remainingPageSpace: 1024, maxPageSpace: 1024)
+        
+        let pages = [
+            [entry1[0], entry2[0], entry3[0]],
+            [entry3[1]],
+            [entry3[2], entry4[0]]
+        ]
+        
+        try await assertInsertionCursor(proposedEntry: 0, pages: pages, pageIndex: nil, blockIndex: nil)
+        try await assertInsertionCursor(proposedEntry: 1, pages: pages, pageIndex: nil, blockIndex: nil)
+        try await assertInsertionCursor(proposedEntry: 2, pages: pages, pageIndex: 0, blockIndex: 0)
+        try await assertInsertionCursor(proposedEntry: 3, pages: pages, pageIndex: 0, blockIndex: 1)
+        try await assertInsertionCursor(proposedEntry: 4, pages: pages, pageIndex: 2, blockIndex: 0)
+        try await assertInsertionCursor(proposedEntry: 5, pages: pages, pageIndex: 2, blockIndex: 1)
+    }
 }