diff --git a/packages/shared/src/components/Markdown.spec.tsx b/packages/shared/src/components/Markdown.spec.tsx
new file mode 100644
index 0000000000..94802bf7cc
--- /dev/null
+++ b/packages/shared/src/components/Markdown.spec.tsx
@@ -0,0 +1,231 @@
+import React from 'react';
+import { QueryClient, QueryClientProvider } from '@tanstack/react-query';
+import { fireEvent, render, screen, within } from '@testing-library/react';
+import Markdown from './Markdown';
+import { LazyModal } from './modals/common/types';
+import { useRequestProtocol } from '../hooks/useRequestProtocol';
+
+const mockOpenModal = jest.fn();
+
+jest.mock('../hooks/useLazyModal', () => ({
+  useLazyModal: () => ({ openModal: mockOpenModal }),
+}));
+
+jest.mock('../hooks/useDomPurify', () => ({
+  useDomPurify: () => ({ sanitize: (content: string) => content }),
+}));
+
+jest.mock('../hooks/useRequestProtocol', () => ({
+  useRequestProtocol: jest.fn(),
+}));
+
+const mockUseRequestProtocol = useRequestProtocol as jest.MockedFunction<
+  typeof useRequestProtocol
+>;
+
+const renderMarkdown = (content: string, container?: HTMLElement) => {
+  const client = new QueryClient();
+
+  return render(
+    <QueryClientProvider client={client}>
+      <Markdown content={content} />
+    </QueryClientProvider>,
+    { container },
+  );
+};
+
+describe('Markdown image interactions', () => {
+  const imageUrl = 'https://media.daily.dev/image/upload/f_auto/v1/posts/abc';
+
+  beforeEach(() => {
+    jest.clearAllMocks();
+    mockUseRequestProtocol.mockReturnValue({
+      requestMethod: jest.fn(),
+      fetchMethod: jest.fn(),
+      isCompanion: false,
+    } as unknown as ReturnType<typeof useRequestProtocol>);
+  });
+
+  it('opens a linked image in the lightbox and prevents navigation', () => {
+    renderMarkdown(
+      `<a href="${imageUrl}" target="_blank" rel="noopener nofollow ugc"><img src="${imageUrl}" alt="Screenshot" /></a>`,
+    );
+
+    const image = screen.getByRole('button', { name: 'Open image' });
+    const event = new MouseEvent('click', {
+      bubbles: true,
+      cancelable: true,
+    });
+
+    image.dispatchEvent(event);
+
+    expect(event.defaultPrevented).toBe(true);
+    expect(mockOpenModal).toHaveBeenCalledTimes(1);
+    expect(mockOpenModal).toHaveBeenCalledWith(
+      expect.objectContaining({
+        type: LazyModal.ImageView,
+        props: expect.objectContaining({
+          src: imageUrl,
+          alt: 'Screenshot',
+          originRect: expect.objectContaining({
+            top: expect.any(Number),
+            left: expect.any(Number),
+            width: expect.any(Number),
+            height: expect.any(Number),
+          }),
+        }),
+      }),
+    );
+  });
+
+  it('opens a linked image from the keyboard and prevents navigation', () => {
+    renderMarkdown(
+      `<a href="${imageUrl}" target="_blank" rel="noopener nofollow ugc"><img src="${imageUrl}" alt="Screenshot" /></a>`,
+    );
+
+    const image = screen.getByRole('button', { name: 'Open image' });
+
+    expect(fireEvent.keyDown(image, { key: 'Enter' })).toBe(false);
+    expect(mockOpenModal).toHaveBeenCalledTimes(1);
+    expect(mockOpenModal).toHaveBeenCalledWith(
+      expect.objectContaining({
+        type: LazyModal.ImageView,
+        props: expect.objectContaining({
+          src: imageUrl,
+          alt: 'Screenshot',
+        }),
+      }),
+    );
+  });
+
+  it('allows an image wrapped by a non-image link to follow that link once', () => {
+    const linkUrl = 'https://github.com/dailydotdev/apps';
+    renderMarkdown(
+      `<a href="${linkUrl}" target="_blank" rel="noopener nofollow ugc"><img src="${imageUrl}" alt="Repository badge" /></a>`,
+    );
+
+    const image = screen.getByRole('button', { name: 'Open image' });
+    const anchor = image.closest('a');
+    const onAnchorClick = jest.fn();
+
+    anchor?.addEventListener('click', onAnchorClick);
+    fireEvent.click(image);
+
+    expect(onAnchorClick).toHaveBeenCalledTimes(1);
+    expect(mockOpenModal).not.toHaveBeenCalled();
+  });
+
+  it('allows an image wrapped by a non-image link to follow that link from the keyboard', () => {
+    const linkUrl = 'https://github.com/dailydotdev/apps';
+    renderMarkdown(
+      `<a href="${linkUrl}" target="_blank" rel="noopener nofollow ugc"><img src="${imageUrl}" alt="Repository badge" /></a>`,
+    );
+
+    const image = screen.getByRole('button', { name: 'Open image' });
+    const anchor = image.closest('a');
+    const onAnchorClick = jest.fn();
+
+    anchor?.addEventListener('click', onAnchorClick);
+    expect(fireEvent.keyDown(image, { key: 'Enter' })).toBe(false);
+
+    expect(onAnchorClick).toHaveBeenCalledTimes(1);
+    expect(mockOpenModal).not.toHaveBeenCalled();
+  });
+
+  it('opens a bare image in the lightbox', () => {
+    renderMarkdown(`<img src="${imageUrl}" alt="Screenshot" />`);
+
+    fireEvent.click(screen.getByRole('button', { name: 'Open image' }));
+
+    expect(mockOpenModal).toHaveBeenCalledTimes(1);
+    expect(mockOpenModal).toHaveBeenCalledWith(
+      expect.objectContaining({
+        type: LazyModal.ImageView,
+        props: expect.objectContaining({
+          src: imageUrl,
+          alt: 'Screenshot',
+        }),
+      }),
+    );
+  });
+
+  it('opens a text link to an image in the lightbox', () => {
+    renderMarkdown(
+      `<a href="https://example.com/screenshot.png?raw=1" target="_blank" rel="noopener nofollow ugc">screenshot</a>`,
+    );
+
+    fireEvent.click(screen.getByRole('link', { name: 'screenshot' }));
+
+    expect(mockOpenModal).toHaveBeenCalledTimes(1);
+    expect(mockOpenModal).toHaveBeenCalledWith(
+      expect.objectContaining({
+        type: LazyModal.ImageView,
+        props: expect.objectContaining({
+          src: 'https://example.com/screenshot.png?raw=1',
+          alt: 'screenshot',
+        }),
+      }),
+    );
+  });
+
+  it('allows text links to daily media videos to navigate', () => {
+    const { container } = renderMarkdown(
+      '<a href="https://media.daily.dev/video/upload/v1/posts/clip.mp4" target="_blank">Watch video</a>',
+      document.createElement('div'),
+    );
+    const { getByRole } = within(container);
+
+    expect(fireEvent.click(getByRole('link', { name: 'Watch video' }))).toBe(
+      true,
+    );
+    expect(mockOpenModal).not.toHaveBeenCalled();
+  });
+
+  describe.each(['image', 'text'])('%s links', (contentType) => {
+    it.each([
+      { metaKey: true },
+      { ctrlKey: true },
+      { shiftKey: true },
+      { altKey: true },
+      { button: 1 },
+    ])('preserves browser navigation for clicks with %j', (options) => {
+      const content =
+        contentType === 'image'
+          ? `<img src="${imageUrl}" alt="Screenshot" />`
+          : 'Screenshot';
+      const { container } = renderMarkdown(
+        `<a href="${imageUrl}" target="_blank">${content}</a>`,
+        document.createElement('div'),
+      );
+      const { getByRole } = within(container);
+
+      const target =
+        contentType === 'image'
+          ? getByRole('button', { name: 'Open image' })
+          : getByRole('link', { name: 'Screenshot' });
+
+      expect(fireEvent.click(target, options)).toBe(true);
+      expect(mockOpenModal).not.toHaveBeenCalled();
+    });
+  });
+
+  it('opens image links in a new tab for the companion', () => {
+    mockUseRequestProtocol.mockReturnValue({
+      requestMethod: jest.fn(),
+      fetchMethod: jest.fn(),
+      isCompanion: true,
+    } as unknown as ReturnType<typeof useRequestProtocol>);
+
+    renderMarkdown(`<img src="${imageUrl}" alt="Screenshot" />`);
+
+    fireEvent.click(screen.getByRole('button', { name: 'Open image' }));
+
+    expect(window.open).toHaveBeenCalledTimes(1);
+    expect(window.open).toHaveBeenCalledWith(
+      imageUrl,
+      '_blank',
+      'noopener,noreferrer',
+    );
+    expect(mockOpenModal).not.toHaveBeenCalled();
+  });
+});
diff --git a/packages/shared/src/components/Markdown.tsx b/packages/shared/src/components/Markdown.tsx
index e1c82bb571..d1d3b2c115 100644
--- a/packages/shared/src/components/Markdown.tsx
+++ b/packages/shared/src/components/Markdown.tsx
@@ -18,6 +18,7 @@ import { useLazyModal } from '../hooks/useLazyModal';
 import { LazyModal } from './modals/common/types';
 import { getImageOriginRect } from './modals/ImageModal';
 import { useRequestProtocol } from '../hooks/useRequestProtocol';
+import { isImageUrl } from '../lib/image';
 
 function isImageElement(
   element: Element | EventTarget,
@@ -25,6 +26,54 @@ function isImageElement(
   return element instanceof HTMLImageElement;
 }
 
+function getTargetElement(target: EventTarget): Element | null {
+  if (target instanceof Element) {
+    return target;
+  }
+
+  if (target instanceof Node) {
+    return target.parentElement;
+  }
+
+  return null;
+}
+
+function getWrappingAnchor(
+  element: Element,
+  container: HTMLElement | null,
+): HTMLAnchorElement | null {
+  let currentElement: Element | null = element;
+
+  while (currentElement && currentElement !== container) {
+    if (currentElement instanceof HTMLAnchorElement) {
+      return currentElement;
+    }
+
+    currentElement = currentElement.parentElement;
+  }
+
+  return null;
+}
+
+function isSameUrl(url: string, otherUrl: string): boolean {
+  try {
+    return new URL(url).href === new URL(otherUrl).href;
+  } catch {
+    return url === otherUrl;
+  }
+}
+
+function shouldOpenAnchorImage(
+  anchor: HTMLAnchorElement | null,
+  imageSrc: string,
+): boolean {
+  if (!anchor?.href) {
+    return true;
+  }
+
+  return isImageUrl(anchor.href) || isSameUrl(anchor.href, imageSrc);
+}
+
 const UserEntityCard = dynamic(() => import('./cards/entity/UserEntityCard'), {
   ssr: false,
 });
@@ -120,19 +169,19 @@ export default function Markdown({
   );
 
   const openImage = useCallback(
-    (element: HTMLImageElement) => {
+    (src: string, alt: string | undefined, originElement: Element) => {
       // The lazy-modal renderer isn't mounted in the extension companion, so
       // fall back to opening the image in a new tab there.
       if (isCompanion) {
-        window.open(element.src, '_blank', 'noopener,noreferrer');
+        window.open(src, '_blank', 'noopener,noreferrer');
         return;
       }
       openModal({
         type: LazyModal.ImageView,
         props: {
-          src: element.src,
-          alt: element.alt || undefined,
-          originRect: getImageOriginRect(element),
+          src,
+          alt,
+          originRect: getImageOriginRect(originElement),
         },
       });
     },
@@ -141,11 +190,38 @@ export default function Markdown({
 
   const onImageClick = useCallback(
     (e: MouseEvent<HTMLDivElement>) => {
-      const element = e.target;
+      if (e.metaKey || e.ctrlKey || e.shiftKey || e.altKey || e.button !== 0) {
+        return;
+      }
+
+      const element = getTargetElement(e.target);
+
+      if (!element) {
+        return;
+      }
+
+      const anchor = getWrappingAnchor(element, containerRef.current);
 
       if (isImageElement(element) && element.src) {
         e.stopPropagation();
-        openImage(element);
+
+        if (!shouldOpenAnchorImage(anchor, element.src)) {
+          return;
+        }
+
+        e.preventDefault();
+        openImage(
+          anchor?.href || element.src,
+          element.alt || undefined,
+          element,
+        );
+        return;
+      }
+
+      if (anchor?.href && isImageUrl(anchor.href)) {
+        e.preventDefault();
+        e.stopPropagation();
+        openImage(anchor.href, anchor.textContent?.trim() || undefined, anchor);
       }
     },
     [openImage],
@@ -153,16 +229,30 @@ export default function Markdown({
 
   const onImageKeyDown = useCallback(
     (e: KeyboardEvent<HTMLDivElement>) => {
-      const element = e.target;
+      const element = getTargetElement(e.target);
 
       if (
+        element &&
         isImageElement(element) &&
         element.src &&
         (e.key === 'Enter' || e.key === ' ')
       ) {
-        e.preventDefault();
+        const anchor = getWrappingAnchor(element, containerRef.current);
+
         e.stopPropagation();
-        openImage(element);
+
+        if (!shouldOpenAnchorImage(anchor, element.src)) {
+          e.preventDefault();
+          anchor?.click();
+          return;
+        }
+
+        e.preventDefault();
+        openImage(
+          anchor?.href || element.src,
+          element.alt || undefined,
+          element,
+        );
       }
     },
     [openImage],
diff --git a/packages/shared/src/components/modals/streaks/StreakRecoverModal.spec.tsx b/packages/shared/src/components/modals/streaks/StreakRecoverModal.spec.tsx
index b657fe4e9b..5b18f8c6eb 100644
--- a/packages/shared/src/components/modals/streaks/StreakRecoverModal.spec.tsx
+++ b/packages/shared/src/components/modals/streaks/StreakRecoverModal.spec.tsx
@@ -202,7 +202,7 @@ it('should render and fetch initial data if logged user can recover streak', asy
   expect(haveFetched).toBeTruthy();
 
   // and rendered
-  const popup = screen.queryByTestId('streak-recover-modal-heading');
+  const popup = await screen.findByTestId('streak-recover-modal-heading');
   expect(popup).toBeInTheDocument();
 });
 
@@ -254,7 +254,7 @@ it('Should have no cost for first time recovery', async () => {
   await waitForNock();
 
   // rendered
-  const popupHeader = screen.queryByTestId('streak-recover-modal-heading');
+  const popupHeader = await screen.findByTestId('streak-recover-modal-heading');
   expect(popupHeader).toBeInTheDocument();
 
   // expect cost to be 0
@@ -282,7 +282,7 @@ it('Should have cost of 100 Cores for 2nd+ time recovery', async () => {
   await waitForNock();
 
   // rendered
-  const popupHeader = screen.queryByTestId('streak-recover-modal-heading');
+  const popupHeader = await screen.findByTestId('streak-recover-modal-heading');
   expect(popupHeader).toBeInTheDocument();
 
   // expect cost to be 100
@@ -310,7 +310,7 @@ it('Should show buy Cores message if user does not have enough Cores', async ()
   await waitForNock();
 
   // rendered
-  const popupHeader = screen.queryByTestId('streak-recover-modal-heading');
+  const popupHeader = await screen.findByTestId('streak-recover-modal-heading');
   expect(popupHeader).toBeInTheDocument();
 
   // expect not enough Cores message
@@ -344,7 +344,7 @@ it('Should show success message on recover', async () => {
   await waitForNock();
 
   // rendered
-  const popupHeader = screen.queryByTestId('streak-recover-modal-heading');
+  const popupHeader = await screen.findByTestId('streak-recover-modal-heading');
   expect(popupHeader).toBeInTheDocument();
 
   // button is there
diff --git a/packages/shared/src/lib/image.spec.ts b/packages/shared/src/lib/image.spec.ts
index 7e0f91dbe6..ce940aaaf4 100644
--- a/packages/shared/src/lib/image.spec.ts
+++ b/packages/shared/src/lib/image.spec.ts
@@ -1,4 +1,4 @@
-import { isPlaceholderImage } from './image';
+import { isImageUrl, isPlaceholderImage } from './image';
 
 describe('isPlaceholderImage', () => {
   it('returns true for API placeholder images', () => {
@@ -42,3 +42,46 @@ describe('isPlaceholderImage', () => {
     expect(isPlaceholderImage('not-a-url')).toBe(false);
   });
 });
+
+describe('isImageUrl', () => {
+  it('matches image file extensions with query strings and fragments', () => {
+    expect(isImageUrl('https://example.com/screenshot.PNG?width=800#top')).toBe(
+      true,
+    );
+    expect(isImageUrl('https://example.com/photo.avif')).toBe(true);
+    expect(isImageUrl('https://example.com/icon.svg')).toBe(true);
+  });
+
+  it('matches daily media and Cloudinary image URLs without extensions', () => {
+    expect(
+      isImageUrl('https://media.daily.dev/image/upload/f_auto/v1/posts/abc'),
+    ).toBe(true);
+    expect(
+      isImageUrl('https://res.cloudinary.com/daily-now/image/upload/abc'),
+    ).toBe(true);
+    expect(
+      isImageUrl('https://daily-now-res.cloudinary.com/image/upload/abc'),
+    ).toBe(true);
+  });
+
+  it('matches protocol-relative and relative image URLs', () => {
+    expect(isImageUrl('//cdn.example.com/image.webp')).toBe(true);
+    expect(isImageUrl('/uploads/image.jpg?raw=1')).toBe(true);
+    expect(isImageUrl('../assets/image.gif')).toBe(true);
+  });
+
+  it('rejects non-image URLs', () => {
+    expect(isImageUrl('https://example.com/articles/123')).toBe(false);
+    expect(
+      isImageUrl('https://res.cloudinary.com/daily-now/raw/upload/abc'),
+    ).toBe(false);
+  });
+
+  it.each([
+    'https://media.daily.dev/video/upload/v1/posts/clip.mp4',
+    'https://media.daily.dev/video/upload/v1/posts/clip',
+    'https://media.daily.dev/raw/upload/v1/posts/document',
+  ])('rejects non-image daily media URLs: %s', (url) => {
+    expect(isImageUrl(url)).toBe(false);
+  });
+});
diff --git a/packages/shared/src/lib/image.ts b/packages/shared/src/lib/image.ts
index 46e748da62..a326b99638 100644
--- a/packages/shared/src/lib/image.ts
+++ b/packages/shared/src/lib/image.ts
@@ -1,5 +1,33 @@
 const DAILY_MEDIA_HOST = 'media.daily.dev';
 const PLACEHOLDER_IMAGE_PATTERN = /placeholder/i;
+const IMAGE_FILE_EXTENSION_PATTERN =
+  /\.(?:apng|avif|bmp|cur|gif|heic|heif|ico|jfif|jpe?g|pjp|pjpeg|png|svg|tiff?|webp)$/i;
+const CLOUDINARY_IMAGE_HOST_PATTERN = /(^|\.)cloudinary\.com$/;
+
+export const isImageUrl = (
+  url: string,
+  baseUrl = globalThis.location?.href ?? 'https://daily.dev',
+): boolean => {
+  if (!url) {
+    return false;
+  }
+
+  try {
+    const parsedUrl = new URL(url, baseUrl);
+    const host = parsedUrl.hostname.toLowerCase();
+
+    if (
+      (host === DAILY_MEDIA_HOST || CLOUDINARY_IMAGE_HOST_PATTERN.test(host)) &&
+      parsedUrl.pathname.includes('/image/')
+    ) {
+      return true;
+    }
+
+    return IMAGE_FILE_EXTENSION_PATTERN.test(parsedUrl.pathname);
+  } catch {
+    return false;
+  }
+};
 
 export const cloudinaryPostImageCoverPlaceholder =
   'https://media.daily.dev/image/upload/s--P4t4XyoV--/f_auto/v1722860399/public/Placeholder%2001';