diff --git a/packages/app/e2e/browser/markdown-image-refresh.spec.ts b/packages/app/e2e/browser/markdown-image-refresh.spec.ts
new file mode 100644
index 0000000000..ca0fd679cd
--- /dev/null
+++ b/packages/app/e2e/browser/markdown-image-refresh.spec.ts
@@ -0,0 +1,91 @@
+import { readFile, writeFile } from "node:fs/promises";
+import path from "node:path";
+import type { Locator, Page } from "@playwright/test";
+import { expect, test } from "../support/fixtures";
+import { openFileExplorer, openFileFromExplorer } from "../support/helpers/file-explorer";
+
+const WHITE = Buffer.from(
+  "iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAQAAAC1HAwCAAAAC0lEQVR42mP8/x8AAusB9Y9ZQmcAAAAASUVORK5CYII=",
+  "base64",
+);
+const BLACK = Buffer.from(
+  "iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAQAAAC1HAwCAAAAC0lEQVR42mNk+A8AAQUBAScY42YAAAAASUVORK5CYII=",
+  "base64",
+);
+
+function embeddedImage(page: Page): Locator {
+  return page.getByRole("button", { name: "hero", exact: true });
+}
+
+function displayedPixel(image: Locator): Promise<number[]> {
+  return image.evaluate((element: HTMLImageElement) => {
+    const canvas = document.createElement("canvas");
+    canvas.width = canvas.height = 1;
+    const context = canvas.getContext("2d")!;
+    context.drawImage(element, 0, 0, 1, 1);
+    return Array.from(context.getImageData(0, 0, 1, 1).data);
+  });
+}
+
+async function createGuide(repoPath: string): Promise<void> {
+  await writeFile(path.join(repoPath, "hero.png"), WHITE);
+  await writeFile(path.join(repoPath, "guide.md"), "# Guide\n\n![hero](./hero.png)\n");
+}
+
+async function openGuidePreview(page: Page): Promise<void> {
+  await openFileExplorer(page);
+  await openFileFromExplorer(page, "guide.md");
+  await expect.poll(() => displayedPixel(embeddedImage(page))).toEqual([255, 255, 255, 255]);
+}
+
+async function replaceEmbeddedImage(repoPath: string): Promise<void> {
+  const imagePath = path.join(repoPath, "hero.png");
+  await writeFile(imagePath, BLACK);
+  expect(await readFile(imagePath)).toEqual(BLACK);
+}
+
+async function expectReplacementInPreview(page: Page): Promise<void> {
+  await expect
+    .configure({ soft: true })
+    .poll(() => displayedPixel(embeddedImage(page)), { timeout: 5000 })
+    .toEqual([0, 0, 0, 255]);
+}
+
+async function remountMarkdownPreview(page: Page): Promise<void> {
+  await page.getByRole("button", { name: "Source", exact: true }).click();
+  await page.getByRole("button", { name: "Preview", exact: true }).click();
+  await expect.poll(() => displayedPixel(embeddedImage(page))).toEqual([0, 0, 0, 255]);
+}
+
+async function expectReplacementWhenOpenedDirectly(page: Page): Promise<void> {
+  await openFileFromExplorer(page, "hero.png");
+  // The standalone image viewer has no accessible name for its image.
+  const image = page.getByTestId("image-file-preview-canvas").locator("img");
+  await expect.poll(() => displayedPixel(image)).toEqual([0, 0, 0, 255]);
+}
+
+test("embedded Markdown image reflects a file replacement while Preview stays open", async ({
+  page,
+  withWorkspace,
+}) => {
+  const workspace = await withWorkspace({ prefix: "markdown-image-refresh-" });
+  await createGuide(workspace.repoPath);
+  await workspace.navigateTo();
+  await openGuidePreview(page);
+  const originalSource = await embeddedImage(page).getAttribute("src");
+
+  await replaceEmbeddedImage(workspace.repoPath);
+  await expectReplacementInPreview(page);
+  await test.info().attach("replacement-observation", {
+    body: JSON.stringify({
+      displayedPixel: await displayedPixel(embeddedImage(page)),
+      sourceUnchanged: originalSource === (await embeddedImage(page).getAttribute("src")),
+      replacementBytesOnDisk: (await readFile(path.join(workspace.repoPath, "hero.png"))).equals(
+        BLACK,
+      ),
+    }),
+    contentType: "application/json",
+  });
+  await remountMarkdownPreview(page);
+  await expectReplacementWhenOpenedDirectly(page);
+});