diff --git a/packages/roosterjs-content-model-dom/lib/constants/ChangeSource.ts b/packages/roosterjs-content-model-dom/lib/constants/ChangeSource.ts
index cbaa372038f1..e2004df5624b 100644
--- a/packages/roosterjs-content-model-dom/lib/constants/ChangeSource.ts
+++ b/packages/roosterjs-content-model-dom/lib/constants/ChangeSource.ts
@@ -70,4 +70,9 @@ export const ChangeSource = {
      * Content changed by replace
      */
     Replace: 'Replace',
+
+    /**
+     * Content changed by dragging content out the editor
+     */
+    DragOutOfEditor: 'DragOutOfEditor',
 };
diff --git a/packages/roosterjs-content-model-plugins/lib/dragAndDrop/DragAndDropPlugin.ts b/packages/roosterjs-content-model-plugins/lib/dragAndDrop/DragAndDropPlugin.ts
index e09254bcc13e..466e800f8db3 100644
--- a/packages/roosterjs-content-model-plugins/lib/dragAndDrop/DragAndDropPlugin.ts
+++ b/packages/roosterjs-content-model-plugins/lib/dragAndDrop/DragAndDropPlugin.ts
@@ -1,6 +1,16 @@
 import { handleDroppedExternalContent } from './utils/handleDroppedExternalContent';
-import type { EditorPlugin, IEditor, PluginEvent } from 'roosterjs-content-model-types';
+import type {
+    EditorPlugin,
+    IEditor,
+    PluginEvent,
+    ReadonlyContentModelSegment,
+} from 'roosterjs-content-model-types';
 import { handleDroppedInternalContent } from './utils/handleDroppedInternalContent';
+import {
+    ChangeSource,
+    getNodePositionFromEvent,
+    getSelectedSegments,
+} from 'roosterjs-content-model-dom';
 
 /**
  * Options for DragAndDrop plugin
@@ -26,6 +36,7 @@ export class DragAndDropPlugin implements EditorPlugin {
     private forbiddenElements: string[] = [];
     private internalDrag: boolean = false;
     private disposer: (() => void) | null = null;
+    private lastSelectSegments: ReadonlyContentModelSegment[] = [];
 
     /**
      * Construct a new instance of DragAndDropPlugin
@@ -59,6 +70,21 @@ export class DragAndDropPlugin implements EditorPlugin {
                     ) {
                         this.adjustDraggingCursor(this.editor, ev as DragEvent);
                     }
+                    editor.formatContentModel(model => {
+                        this.lastSelectSegments = getSelectedSegments(
+                            model,
+                            false /* includingFormatHolder */
+                        );
+                        return false;
+                    });
+                },
+            },
+            dragend: {
+                beforeDispatch: ev => {
+                    if (this.internalDrag) {
+                        const dropEvent = ev as DragEvent;
+                        this.triggerDragOutOfTheEditor(editor, dropEvent);
+                    }
                 },
             },
         });
@@ -76,6 +102,8 @@ export class DragAndDropPlugin implements EditorPlugin {
             this.disposer = null;
         }
         this.forbiddenElements = [];
+        this.internalDrag = false;
+        this.lastSelectSegments = [];
     }
 
     /**
@@ -92,6 +120,7 @@ export class DragAndDropPlugin implements EditorPlugin {
                 this.editor.isExperimentalFeatureEnabled('HandleDropInternalContent')
             ) {
                 handleDroppedInternalContent(this.editor, dropEvent);
+                this.lastSelectSegments = [];
             } else if (!this.internalDrag) {
                 const html = dropEvent.dataTransfer?.getData('text/html');
                 if (html) {
@@ -120,4 +149,31 @@ export class DragAndDropPlugin implements EditorPlugin {
             }
         }
     }
+
+    private triggerDragOutOfTheEditor(editor: IEditor, dropEvent: DragEvent) {
+        const dropPosition = editor.isExperimentalFeatureEnabled('HandleDropInternalContent')
+            ? undefined
+            : getNodePositionFromEvent(
+                  editor.getDocument(),
+                  editor.getDOMHelper(),
+                  dropEvent.clientX,
+                  dropEvent.clientY
+              );
+        let modelChanged: boolean = false;
+        editor.formatContentModel(model => {
+            const selectedSegments = getSelectedSegments(model, false /* includingFormatHolder */);
+            modelChanged =
+                this.lastSelectSegments.length !== selectedSegments.length ||
+                this.lastSelectSegments.some(
+                    (segment, index) => segment !== selectedSegments[index]
+                );
+            return false;
+        });
+        if (!dropPosition && modelChanged) {
+            editor.triggerEvent('contentChanged', {
+                source: ChangeSource.DragOutOfEditor,
+            });
+            editor.takeSnapshot();
+        }
+    }
 }
diff --git a/packages/roosterjs-content-model-plugins/test/dragAndDrop/DragAndDropPluginTest.ts b/packages/roosterjs-content-model-plugins/test/dragAndDrop/DragAndDropPluginTest.ts
index 972640282804..e297c3fafc8b 100644
--- a/packages/roosterjs-content-model-plugins/test/dragAndDrop/DragAndDropPluginTest.ts
+++ b/packages/roosterjs-content-model-plugins/test/dragAndDrop/DragAndDropPluginTest.ts
@@ -1,7 +1,8 @@
 import * as handleDroppedContentFile from '../../lib/dragAndDrop/utils/handleDroppedExternalContent';
 import * as handleDroppedInternalContentFile from '../../lib/dragAndDrop/utils/handleDroppedInternalContent';
 import { DragAndDropPlugin } from '../../lib/dragAndDrop/DragAndDropPlugin';
-import { IEditor } from 'roosterjs-content-model-types';
+import { ContentModelDocument, IEditor } from 'roosterjs-content-model-types';
+import { ChangeSource } from 'roosterjs-content-model-dom';
 
 describe('DragAndDropPlugin', () => {
     let plugin: DragAndDropPlugin;
@@ -11,6 +12,9 @@ describe('DragAndDropPlugin', () => {
     let isExperimentalFeatureEnabledSpy: jasmine.Spy;
     let eventMap: Record<string, any>;
     let getDOMSelectionSpy: jasmine.Spy;
+    let takeSnapshotSpy: jasmine.Spy;
+    let triggerEventSpy: jasmine.Spy;
+    let contentModel: ContentModelDocument;
 
     beforeEach(() => {
         disposerSpy = jasmine.createSpy('disposer');
@@ -22,11 +26,21 @@ describe('DragAndDropPlugin', () => {
             .createSpy('isExperimentalFeatureEnabled')
             .and.returnValue(true);
         getDOMSelectionSpy = jasmine.createSpy('getDOMSelection');
+        takeSnapshotSpy = jasmine.createSpy('takeSnapshot');
+        triggerEventSpy = jasmine.createSpy('triggerEvent');
+        contentModel = {
+            blockGroupType: 'Document',
+            blocks: [],
+        };
 
         editor = ({
             attachDomEvent: attachDomEventSpy,
             isExperimentalFeatureEnabled: isExperimentalFeatureEnabledSpy,
             getDOMSelection: getDOMSelectionSpy,
+            takeSnapshot: takeSnapshotSpy,
+            triggerEvent: triggerEventSpy,
+            formatContentModel: (callback: (model: ContentModelDocument) => void) =>
+                callback(contentModel),
         } as any) as IEditor;
     });
 
@@ -46,6 +60,7 @@ describe('DragAndDropPlugin', () => {
 
             expect(attachDomEventSpy).toHaveBeenCalled();
             expect(eventMap.dragstart).toBeDefined();
+            expect(eventMap.dragend).toBeDefined();
         });
 
         it('should initialize with custom forbidden elements', () => {
@@ -94,6 +109,58 @@ describe('DragAndDropPlugin', () => {
         });
     });
 
+    describe('dragend event', () => {
+        it('should trigger contentChanged and take a snapshot when the model changed', () => {
+            spyOn(handleDroppedInternalContentFile, 'handleDroppedInternalContent');
+            plugin = new DragAndDropPlugin();
+            plugin.initialize(editor);
+
+            contentModel.blocks.push({
+                blockType: 'Paragraph',
+                segments: [
+                    {
+                        segmentType: 'Text',
+                        text: 'test',
+                        format: {},
+                        isSelected: true,
+                    },
+                ],
+                format: {},
+            });
+            eventMap.dragstart.beforeDispatch({} as DragEvent);
+            contentModel.blocks = [];
+
+            eventMap.dragend.beforeDispatch({} as DragEvent);
+
+            expect(triggerEventSpy).toHaveBeenCalledWith('contentChanged', {
+                source: ChangeSource.DragOutOfEditor,
+            });
+            expect(takeSnapshotSpy).toHaveBeenCalledTimes(1);
+        });
+
+        it('should not take a snapshot when the model did not change', () => {
+            plugin = new DragAndDropPlugin();
+            plugin.initialize(editor);
+
+            const target = document.createElement('div');
+            eventMap.dragstart.beforeDispatch({ target } as any);
+            eventMap.dragend.beforeDispatch({} as any);
+
+            expect(triggerEventSpy).not.toHaveBeenCalled();
+            expect(takeSnapshotSpy).not.toHaveBeenCalled();
+        });
+
+        it('should not take a snapshot when drag ends without an internal drag', () => {
+            plugin = new DragAndDropPlugin();
+            plugin.initialize(editor);
+
+            eventMap.dragend.beforeDispatch({} as any);
+
+            expect(triggerEventSpy).not.toHaveBeenCalled();
+            expect(takeSnapshotSpy).not.toHaveBeenCalled();
+        });
+    });
+
     describe('onPluginEvent - beforeDrop', () => {
         let handleDroppedExternalContentSpy: jasmine.Spy;