diff --git a/ts/components/MediaEditor.dom.tsx b/ts/components/MediaEditor.dom.tsx
index 0672b66682..97d3db8428 100644
--- a/ts/components/MediaEditor.dom.tsx
+++ b/ts/components/MediaEditor.dom.tsx
@@ -325,7 +325,6 @@ export function MediaEditor({
         width: img.width,
       };
       setImageState(newImageState);
-      takeSnapshot('initial state', newImageState, canvas);
     };
     img.onerror = (
       event: Event | string,
@@ -588,6 +587,20 @@ export function MediaEditor({
     drawFabricBackgroundImage({ fabricCanvas, image, imageState });
   }, [fabricCanvas, image, imageState]);
 
+  const initialSnapshotTaken = useRef(false);
+  useEffect(() => {
+    if (
+      !fabricCanvas ||
+      !fabricCanvas.backgroundImage ||
+      initialSnapshotTaken.current
+    ) {
+      return;
+    }
+
+    takeSnapshot('initial state', imageState, fabricCanvas);
+    initialSnapshotTaken.current = true;
+  }, [fabricCanvas, imageState, takeSnapshot]);
+
   const [canCrop, setCanCrop] = useState(false);
   const [cropAspectRatioLock, setCropAspectRatioLock] = useState(false);
   const [drawTool, setDrawTool] = useState<DrawTool>(DrawTool.Pen);
diff --git a/ts/test-mock/messaging/media_editor_test.ts b/ts/test-mock/messaging/media_editor_test.ts
new file mode 100644
index 0000000000..18dc5ea8ea
--- /dev/null
+++ b/ts/test-mock/messaging/media_editor_test.ts
@@ -0,0 +1,174 @@
+// Copyright 2025 Signal Messenger, LLC
+// SPDX-License-Identifier: AGPL-3.0-only
+
+import { expect } from 'playwright/test';
+import { type PrimaryDevice, StorageState } from '@signalapp/mock-server';
+import * as path from 'node:path';
+
+import type { App } from '../playwright.js';
+import { Bootstrap } from '../bootstrap.js';
+import { composerAttachImages } from '../helpers.js';
+import * as durations from '../../util/durations/index.js';
+
+const CAT_PATH = path.join(
+  __dirname,
+  '..',
+  '..',
+  '..',
+  'fixtures',
+  'cat-screenshot.png'
+);
+
+describe('MediaEditor', function (this: Mocha.Suite) {
+  this.timeout(durations.MINUTE);
+
+  let bootstrap: Bootstrap;
+  let app: App;
+  let pinned: PrimaryDevice;
+
+  beforeEach(async () => {
+    bootstrap = new Bootstrap();
+    await bootstrap.init();
+
+    let state = StorageState.getEmpty();
+
+    const { phone, contacts } = bootstrap;
+    [pinned] = contacts;
+
+    state = state.addContact(pinned, {
+      identityKey: pinned.publicKey.serialize(),
+      profileKey: pinned.profileKey.serialize(),
+      whitelisted: true,
+    });
+
+    state = state.pin(pinned);
+    await phone.setStorageState(state);
+
+    app = await bootstrap.link();
+  });
+
+  afterEach(async function (this: Mocha.Context) {
+    if (!bootstrap) {
+      return;
+    }
+
+    await bootstrap.maybeSaveLogs(this.currentTest, app);
+    await app.close();
+    await bootstrap.teardown();
+  });
+
+  async function openMediaEditor(page: Awaited<ReturnType<App['getWindow']>>) {
+    await page.getByTestId(pinned.device.aci).click();
+
+    await composerAttachImages(page, [CAT_PATH]);
+
+    const AttachmentsList = page.locator('.module-attachments');
+    await AttachmentsList.waitFor({ state: 'visible' });
+
+    const EditableAttachment = AttachmentsList.locator(
+      '.module-attachments--editable'
+    ).first();
+    await EditableAttachment.waitFor({ state: 'visible' });
+
+    const StagedImage = EditableAttachment.locator('.module-image--loaded');
+    await StagedImage.waitFor({ state: 'visible' });
+
+    await StagedImage.click();
+
+    const MediaEditor = page.locator('.MediaEditor');
+    await MediaEditor.waitFor({ state: 'visible' });
+
+    return MediaEditor;
+  }
+
+  async function drawLineOnCanvas(
+    page: Awaited<ReturnType<App['getWindow']>>,
+    MediaEditor: Awaited<ReturnType<typeof openMediaEditor>>,
+    options?: {
+      startX?: number;
+      startY?: number;
+      endX?: number;
+      endY?: number;
+    }
+  ) {
+    const canvas = MediaEditor.locator('.MediaEditor__media--canvas').first();
+    const canvasBox = await canvas.boundingBox();
+
+    if (!canvasBox) {
+      throw new Error('Canvas bounding box not found');
+    }
+
+    // Draw diagonal line by default
+    const startX = options?.startX ?? canvasBox.x + canvasBox.width * 0.3;
+    const startY = options?.startY ?? canvasBox.y + canvasBox.height * 0.3;
+    const endX = options?.endX ?? canvasBox.x + canvasBox.width * 0.7;
+    const endY = options?.endY ?? canvasBox.y + canvasBox.height * 0.7;
+
+    await page.mouse.move(startX, startY);
+    await page.mouse.down();
+    await page.mouse.move(endX, endY);
+    await page.mouse.up();
+  }
+
+  it('can undo after drawing a line', async () => {
+    const page = await app.getWindow();
+    const MediaEditor = await openMediaEditor(page);
+
+    const canvas = MediaEditor.locator('.MediaEditor__media--canvas').first();
+
+    const screenshotBeforeDrawing = await canvas.screenshot();
+
+    const DrawButton = MediaEditor.locator('.MediaEditor__control--pen');
+    await DrawButton.click();
+
+    await page.waitForTimeout(100);
+
+    await drawLineOnCanvas(page, MediaEditor);
+
+    await page.waitForTimeout(100);
+
+    const screenshotAfterDrawing = await canvas.screenshot();
+
+    const UndoButton = MediaEditor.locator('.MediaEditor__control--undo');
+    await expect(UndoButton).toBeEnabled();
+    await UndoButton.click();
+
+    await page.waitForTimeout(100);
+
+    const screenshotAfterUndo = await canvas.screenshot();
+
+    expect(
+      Buffer.compare(screenshotBeforeDrawing, screenshotAfterDrawing),
+      'screenshots before and after drawing should be different'
+    ).not.toBe(0);
+
+    expect(
+      Buffer.compare(screenshotBeforeDrawing, screenshotAfterUndo),
+      'screenshot before drawing should be the same as after undo'
+    ).toBe(0);
+  });
+
+  it('undo button is disabled when there is nothing to undo', async () => {
+    const page = await app.getWindow();
+    const MediaEditor = await openMediaEditor(page);
+
+    const UndoButton = MediaEditor.locator('.MediaEditor__control--undo');
+    await expect(UndoButton).toBeDisabled();
+
+    const DrawButton = MediaEditor.locator('.MediaEditor__control--pen');
+    await DrawButton.click();
+
+    await page.waitForTimeout(100);
+
+    await drawLineOnCanvas(page, MediaEditor);
+
+    await page.waitForTimeout(100);
+
+    await expect(UndoButton).toBeEnabled();
+    await UndoButton.click();
+
+    await page.waitForTimeout(100);
+
+    await expect(UndoButton).toBeDisabled();
+  });
+});
diff --git a/ts/util/lint/exceptions.json b/ts/util/lint/exceptions.json
index 16d7d7562d..18af37ce33 100644
--- a/ts/util/lint/exceptions.json
+++ b/ts/util/lint/exceptions.json
@@ -2327,5 +2327,12 @@
     "line": "  message.innerHTML = window.SignalContext.i18n('icu:optimizingApplication');",
     "reasonCategory": "usageTrusted",
     "updated": "2021-09-17T21:02:59.414Z"
+  },
+  {
+    "rule": "React-useRef",
+    "path": "ts/components/MediaEditor.tsx",
+    "line": "  const initialSnapshotTaken = useRef(false);",
+    "reasonCategory": "usageTrusted",
+    "updated": "2025-10-10T09:45:25.353Z"
   }
 ]