diff --git a/src/components/ChannelPreview/utils.tsx b/src/components/ChannelPreview/utils.tsx
index e8903334d0..636a75a775 100644
--- a/src/components/ChannelPreview/utils.tsx
+++ b/src/components/ChannelPreview/utils.tsx
@@ -6,13 +6,14 @@ import type { Channel, PollVote, TranslationLanguages, UserResponse } from 'stre
 import type { TranslationContextValue } from '../../context/TranslationContext';
 import type { ChatContextValue } from '../../context';
 import type { PluggableList } from 'unified';
-import { htmlToTextPlugin, plusPlusToEmphasis } from '../Message';
+import { htmlToTextPlugin, imageToLink, plusPlusToEmphasis } from '../Message';
 import remarkGfm from 'remark-gfm';
 
 const remarkPlugins: PluggableList = [
   htmlToTextPlugin,
   [remarkGfm, { singleTilde: false }],
   plusPlusToEmphasis,
+  imageToLink,
 ];
 
 export const renderPreviewText = (text: string) => (
diff --git a/src/components/Message/renderText/__tests__/renderText.test.js b/src/components/Message/renderText/__tests__/renderText.test.js
index be2161e282..8827aa073d 100644
--- a/src/components/Message/renderText/__tests__/renderText.test.js
+++ b/src/components/Message/renderText/__tests__/renderText.test.js
@@ -4,6 +4,7 @@ import { u } from 'unist-builder';
 import { render, screen } from '@testing-library/react';
 import {
   htmlToTextPlugin,
+  imageToLink,
   keepLineBreaksPlugin,
   plusPlusToEmphasis,
 } from '../remarkPlugins';
@@ -449,18 +450,53 @@ describe('plusPlusToEmphasis', () => {
   };
 
   it('++…++ renders as <ins> and ignores code/links', () => {
-    renderTextPlusPlus('This is ++inserted++ and `++not++` and [x](y) ++also++');
+    renderTextPlusPlus(
+      'This is ++inserted++ and `++not++` and [x](https://octodex.github.com/images/minion.png) ++also++',
+    );
     expect(screen.getByText('inserted', { selector: 'ins' })).toBeInTheDocument();
     expect(screen.getByText('++not++', { selector: 'code' })).toBeInTheDocument();
     // link text exists; its inner text shouldn't be transformed
-    // expect(screen.getByRole('link', { name: 'x' })).toBeInTheDocument();
+    expect(screen.getByRole('link', { name: 'x' })).toBeInTheDocument();
   });
 
   it('does not render ++…++  as <ins> if not present', () => {
-    renderTextPlusPlus('This is ++inserted++ and `++not++` and [x](y) ++also++', false);
+    renderTextPlusPlus(
+      'This is ++inserted++ and `++not++` and [x](https://octodex.github.com/images/minion.png) ++also++',
+      false,
+    );
     expect(screen.queryByText('inserted', { selector: 'ins' })).not.toBeInTheDocument();
     expect(screen.getByText('++not++', { selector: 'code' })).toBeInTheDocument();
     // link text exists; its inner text shouldn't be transformed
-    // expect(screen.getByRole('link', { name: 'x' })).toBeInTheDocument();
+    expect(screen.getByRole('link', { name: 'x' })).toBeInTheDocument();
+  });
+});
+
+describe('imageToLink', () => {
+  const renderImageToLink = (text, withPlugin = true) => {
+    const Markdown = renderText(
+      text,
+      {},
+      { getRemarkPlugins: () => (withPlugin ? [imageToLink] : []) },
+    );
+    return render(Markdown).container;
+  };
+
+  it('converts image link to anchor link', () => {
+    renderImageToLink('Before ![x](https://octodex.github.com/images/minion.png) After');
+    expect(
+      screen.getByRole('link', { name: 'https://octodex.github.com/images/minion.png' }),
+    ).toBeInTheDocument();
+  });
+
+  it('does not convert image link to anchor link if plugin is missing', () => {
+    renderImageToLink(
+      'Before ![x](https://octodex.github.com/images/minion.png) After',
+      false,
+    );
+    expect(
+      screen.queryByRole('link', {
+        name: 'https://octodex.github.com/images/minion.png',
+      }),
+    ).not.toBeInTheDocument();
   });
 });
diff --git a/src/components/Message/renderText/remarkPlugins/imageToLink.ts b/src/components/Message/renderText/remarkPlugins/imageToLink.ts
new file mode 100644
index 0000000000..6eca7d1342
--- /dev/null
+++ b/src/components/Message/renderText/remarkPlugins/imageToLink.ts
@@ -0,0 +1,43 @@
+import { SKIP, visit, type VisitorResult } from 'unist-util-visit';
+import type { Image, Link, Parent, Text } from 'mdast';
+import type { Node } from 'unist';
+
+type ImgVisitor = (
+  node: Image,
+  index: number | null,
+  parent: Parent | null,
+) => VisitorResult;
+
+export type ImageToLinkPluginOptions = {
+  getTextLabelFrom?: 'alt' | 'title' | 'url';
+};
+
+const text = (value: string): Text => ({ type: 'text', value });
+
+/**
+ * Converts image Markdown links (![Minion](https://octodex.github.com/images/minion.png))
+ * to HTML <a href={url}>{url | title | alt}</a>
+ *
+ * By default, the anchor text content is the image url so that image preview can be generated / enriched on the server.
+ * @param getTextLabelFrom
+ */
+export function imageToLink({ getTextLabelFrom = 'url' }: ImageToLinkPluginOptions = {}) {
+  return (tree: Node) => {
+    const visitor: ImgVisitor = (node, index, parent) => {
+      if (parent == null || index == null) return;
+
+      const label = node[getTextLabelFrom] ?? node.url; // node.alt || node.title || node.url;
+      const link: Link = {
+        children: [text(label)],
+        title: node.title ?? node.alt ?? node.url,
+        type: 'link',
+        url: node.url,
+      };
+
+      parent.children.splice(index, 1, link);
+      return [SKIP, index + 1] as const;
+    };
+
+    visit(tree, 'image', visitor);
+  };
+}
diff --git a/src/components/Message/renderText/remarkPlugins/index.ts b/src/components/Message/renderText/remarkPlugins/index.ts
index 35cb04faf9..f77d648b88 100644
--- a/src/components/Message/renderText/remarkPlugins/index.ts
+++ b/src/components/Message/renderText/remarkPlugins/index.ts
@@ -1,3 +1,4 @@
 export * from './htmlToTextPlugin';
+export * from './imageToLink';
 export * from './keepLineBreaksPlugin';
 export * from './plusPlusToEmphasis';
diff --git a/src/components/Message/renderText/renderText.tsx b/src/components/Message/renderText/renderText.tsx
index 731e039014..aef7ba0ddf 100644
--- a/src/components/Message/renderText/renderText.tsx
+++ b/src/components/Message/renderText/renderText.tsx
@@ -12,6 +12,7 @@ import { detectHttp, matchMarkdownLinks, messageCodeBlocks } from './regex';
 import { emojiMarkdownPlugin, mentionsMarkdownPlugin } from './rehypePlugins';
 import {
   htmlToTextPlugin,
+  imageToLink,
   keepLineBreaksPlugin,
   plusPlusToEmphasis,
 } from './remarkPlugins';
@@ -175,6 +176,7 @@ export const renderText = (
     keepLineBreaksPlugin,
     [remarkGfm, { singleTilde: false }],
     plusPlusToEmphasis,
+    imageToLink,
   ];
   const rehypePlugins: PluggableList = [emojiMarkdownPlugin];