diff --git a/packages/flutter/lib/src/widgets/text_selection.dart b/packages/flutter/lib/src/widgets/text_selection.dart
index dd308fb6627a8..825b8cf9a4b73 100644
--- a/packages/flutter/lib/src/widgets/text_selection.dart
+++ b/packages/flutter/lib/src/widgets/text_selection.dart
@@ -582,11 +582,12 @@ class TextSelectionOverlay {
     if (!renderObject.attached) {
       return;
     }
-    final Size handleSize = selectionControls!.getHandleSize(
-      renderObject.preferredLineHeight,
-    );
 
-    _dragEndPosition = details.globalPosition + Offset(0.0, -handleSize.height);
+    // This adjusts for the fact that the selection handles may not
+    // perfectly cover the TextPosition that they correspond to.
+    final Offset offsetFromHandleToTextPosition = _getOffsetToTextPositionPoint(_selectionOverlay.endHandleType);
+    _dragEndPosition = details.globalPosition + offsetFromHandleToTextPosition;
+
     final TextPosition position = renderObject.getPositionForPoint(_dragEndPosition);
 
     _selectionOverlay.showMagnifier(
@@ -660,10 +661,12 @@ class TextSelectionOverlay {
     if (!renderObject.attached) {
       return;
     }
-    final Size handleSize = selectionControls!.getHandleSize(
-      renderObject.preferredLineHeight,
-    );
-    _dragStartPosition = details.globalPosition + Offset(0.0, -handleSize.height);
+
+    // This adjusts for the fact that the selection handles may not
+    // perfectly cover the TextPosition that they correspond to.
+    final Offset offsetFromHandleToTextPosition = _getOffsetToTextPositionPoint(_selectionOverlay.startHandleType);
+    _dragStartPosition = details.globalPosition + offsetFromHandleToTextPosition;
+
     final TextPosition position = renderObject.getPositionForPoint(_dragStartPosition);
 
     _selectionOverlay.showMagnifier(
@@ -731,6 +734,32 @@ class TextSelectionOverlay {
 
   void _handleAnyDragEnd(DragEndDetails details) => _selectionOverlay.hideMagnifier(shouldShowToolbar: !_selection.isCollapsed);
 
+  // Returns the offset that locates a drag on a handle to the correct line of text.
+  Offset _getOffsetToTextPositionPoint(TextSelectionHandleType type) {
+    final Size handleSize = selectionControls!.getHandleSize(
+      renderObject.preferredLineHeight,
+    );
+
+    // Try to shift center of handle to top by half of handle height.
+    final double halfHandleHeight = handleSize.height / 2;
+
+    // [getHandleAnchor] is used to shift the selection endpoint to the top left
+    // point of the handle rect when building the handle widget.
+    // The endpoint is at the bottom of the selection rect, which is also at the
+    // bottom of the line of text.
+    // Try to shift the top of the handle to the selection endpoint by the dy of
+    // the handle's anchor.
+    final double handleAnchorDy = selectionControls!.getHandleAnchor(type, renderObject.preferredLineHeight).dy;
+
+    // Try to shift the selection endpoint to the center of the correct line by
+    // using half of the line height.
+    final double halfPreferredLineHeight = renderObject.preferredLineHeight / 2;
+
+    // The x offset is accurate, so we only need to adjust the y position.
+    final double offsetYFromHandleToTextPosition = handleAnchorDy - halfHandleHeight - halfPreferredLineHeight;
+    return Offset(0.0, offsetYFromHandleToTextPosition);
+  }
+
   void _handleSelectionHandleChanged(TextSelection newSelection, {required bool isEnd}) {
     final TextPosition textPosition = isEnd ? newSelection.extent : newSelection.base;
     selectionDelegate.userUpdateTextEditingValue(
diff --git a/packages/flutter/test/cupertino/text_field_test.dart b/packages/flutter/test/cupertino/text_field_test.dart
index fe2b8521a5b1f..f646deec9186d 100644
--- a/packages/flutter/test/cupertino/text_field_test.dart
+++ b/packages/flutter/test/cupertino/text_field_test.dart
@@ -6805,4 +6805,101 @@ void main() {
       }, variant: TargetPlatformVariant.all());
     });
   });
+
+  testWidgets('Can drag handles to change selection correctly in multiline', (WidgetTester tester) async {
+    final TextEditingController controller = TextEditingController();
+
+    await tester.pumpWidget(
+      CupertinoApp(
+        debugShowCheckedModeBanner: false,
+        home: CupertinoPageScaffold(
+          child: CupertinoTextField(
+            dragStartBehavior: DragStartBehavior.down,
+            controller: controller,
+            style: const TextStyle(color: Colors.black, fontSize: 34.0),
+            maxLines: 3,
+          ),
+        ),
+      ),
+    );
+
+    const String testValue =
+        'First line of text is\n'
+        'Second line goes until\n'
+        'Third line of stuff';
+
+    const String cutValue =
+        'First line of text is\n'
+        'Second until\n'
+        'Third line of stuff';
+    await tester.enterText(find.byType(CupertinoTextField), testValue);
+
+    // Skip past scrolling animation.
+    await tester.pump();
+    await tester.pumpAndSettle(const Duration(milliseconds: 200));
+
+    // Check that the text spans multiple lines.
+    final Offset firstPos = textOffsetToPosition(tester, testValue.indexOf('First'));
+    final Offset secondPos = textOffsetToPosition(tester, testValue.indexOf('Second'));
+    final Offset thirdPos = textOffsetToPosition(tester, testValue.indexOf('Third'));
+    expect(firstPos.dx, secondPos.dx);
+    expect(firstPos.dx, thirdPos.dx);
+    expect(firstPos.dy, lessThan(secondPos.dy));
+    expect(secondPos.dy, lessThan(thirdPos.dy));
+
+    // Double tap on the 'n' in 'until' to select the word.
+    final Offset untilPos = textOffsetToPosition(tester, testValue.indexOf('until')+1);
+    await tester.tapAt(untilPos);
+    await tester.pump(const Duration(milliseconds: 50));
+    await tester.tapAt(untilPos);
+    await tester.pumpAndSettle();
+
+    // Skip past the frame where the opacity is zero.
+    await tester.pump(const Duration(milliseconds: 200));
+
+    expect(controller.selection.baseOffset, 39);
+    expect(controller.selection.extentOffset, 44);
+
+    final RenderEditable renderEditable = findRenderEditable(tester);
+    final List<TextSelectionPoint> endpoints = globalize(
+      renderEditable.getEndpointsForSelection(controller.selection),
+      renderEditable,
+    );
+    expect(endpoints.length, 2);
+
+    final Offset offsetFromEndPointToMiddlePoint = Offset(0.0, -renderEditable.preferredLineHeight / 2);
+
+    // Drag the left handle to just after 'Second', still on the second line.
+    Offset handlePos = endpoints[0].point + offsetFromEndPointToMiddlePoint;
+    Offset newHandlePos = textOffsetToPosition(tester, testValue.indexOf('Second') + 6) + offsetFromEndPointToMiddlePoint;
+    TestGesture gesture = await tester.startGesture(handlePos, pointer: 7);
+    await tester.pump();
+    await gesture.moveTo(newHandlePos);
+    await tester.pump();
+    await gesture.up();
+    await tester.pump();
+
+    expect(controller.selection.baseOffset, 28);
+    expect(controller.selection.extentOffset, 44);
+
+    // Drag the right handle to just after 'goes', still on the second line.
+    handlePos = endpoints[1].point + offsetFromEndPointToMiddlePoint;
+    newHandlePos = textOffsetToPosition(tester, testValue.indexOf('goes') + 4) + offsetFromEndPointToMiddlePoint;
+    gesture = await tester.startGesture(handlePos, pointer: 7);
+    await tester.pump();
+    await gesture.moveTo(newHandlePos);
+    await tester.pump();
+    await gesture.up();
+    await tester.pump();
+
+    expect(controller.selection.baseOffset, 28);
+    expect(controller.selection.extentOffset, 38);
+
+    if (!isContextMenuProvidedByPlatform) {
+      await tester.tap(find.text('Cut'));
+      await tester.pump();
+      expect(controller.selection.isCollapsed, true);
+      expect(controller.text, cutValue);
+    }
+  });
 }