diff --git a/packages/ui/src/components/chat/MarkdownImageGallery.tsx b/packages/ui/src/components/chat/MarkdownImageGallery.tsx
index faffc569..ba529d95 100644
--- a/packages/ui/src/components/chat/MarkdownImageGallery.tsx
+++ b/packages/ui/src/components/chat/MarkdownImageGallery.tsx
@@ -1,25 +1,81 @@
 import React from 'react';
+import { toast } from 'sonner';
 import { Icon } from '@/components/icon/Icon';
 import { useEffectiveDirectory } from '@/hooks/useEffectiveDirectory';
+import { useI18n } from '@/lib/i18n';
+import {
+  acquireRuntimeUrlAuthToken,
+  refreshRuntimeUrlAuthToken,
+  subscribeRuntimeUrlAuthToken,
+} from '@/lib/runtime-auth';
+import { getRuntimeApiBaseUrl } from '@/lib/runtime-switch';
 import type { ToolPopupContent } from './message/types';
 import {
   extractMarkdownImageCandidates,
   MAX_MARKDOWN_IMAGE_COUNT,
   type MarkdownImageCandidate,
 } from './markdown/markdownCore';
-import { resolveMarkdownImageSource } from './markdown/markdownImageAssets';
+import {
+  getPreparedMarkdownImageUrl,
+  isLocalMarkdownImageSource,
+  prepareLocalMarkdownImages,
+  resolveMarkdownImageSource,
+  type PreparedMarkdownImage,
+} from './markdown/markdownImageAssets';
+
+const useAssetAuth = (enabled: boolean): { ready: boolean; nonce: number } => {
+  const [ready, setReady] = React.useState(false);
+  const [nonce, setNonce] = React.useState(0);
+  const apiBaseUrl = getRuntimeApiBaseUrl();
+
+  React.useEffect(() => {
+    if (!enabled) {
+      setReady(false);
+      return;
+    }
+    let cancelled = false;
+    let retryTimer: ReturnType<typeof setTimeout> | undefined;
+    const release = acquireRuntimeUrlAuthToken(apiBaseUrl);
+    const unsubscribe = subscribeRuntimeUrlAuthToken(() => {
+      if (!cancelled) setNonce((current) => current + 1);
+    });
+    const refresh = () => {
+      void refreshRuntimeUrlAuthToken(apiBaseUrl)
+        .then(() => {
+          if (!cancelled) setReady(true);
+        })
+        .catch(() => {
+          if (!cancelled) retryTimer = setTimeout(refresh, 1000);
+        });
+    };
+    refresh();
+    return () => {
+      cancelled = true;
+      if (retryTimer) clearTimeout(retryTimer);
+      release();
+      unsubscribe();
+    };
+  }, [apiBaseUrl, enabled]);
+
+  return { ready: !enabled || ready, nonce };
+};
 
 const MarkdownImageThumbnail: React.FC<{
   candidate: MarkdownImageCandidate;
+  preparation?: PreparedMarkdownImage;
   directory: string;
+  assetAuthReady: boolean;
+  assetAuthNonce: number;
   onShowPopup?: (content: ToolPopupContent) => void;
-}> = ({ candidate, directory, onShowPopup }) => {
+}> = ({ candidate, preparation, directory, assetAuthReady, assetAuthNonce, onShowPopup }) => {
+  const { t } = useI18n();
   const thumbnailRef = React.useRef<HTMLButtonElement>(null);
   const [shouldLoad, setShouldLoad] = React.useState(false);
-  const [image, setImage] = React.useState<{
-    url: string;
-    status: 'loading' | 'ready' | 'error';
-  }>({ url: '', status: 'loading' });
+  const [image, setImage] = React.useState<{ url: string; status: 'loading' | 'ready' | 'error' }>({
+    url: '',
+    status: 'loading',
+  });
+  const local = isLocalMarkdownImageSource(candidate.source);
 
   React.useEffect(() => {
     const thumbnail = thumbnailRef.current;
@@ -28,7 +84,6 @@ const MarkdownImageThumbnail: React.FC<{
       setShouldLoad(true);
       return;
     }
-
     const observer = new IntersectionObserver((entries) => {
       if (!entries.some((entry) => entry.isIntersecting)) return;
       setShouldLoad(true);
@@ -39,20 +94,33 @@ const MarkdownImageThumbnail: React.FC<{
   }, [shouldLoad]);
 
   React.useEffect(() => {
-    if (!shouldLoad) return;
+    if (!shouldLoad || (local && !preparation)) return;
+    if (local) {
+      if (preparation?.status !== 'ready') {
+        setImage({ url: '', status: 'error' });
+        return;
+      }
+      if (!assetAuthReady) return;
+      setImage({ url: getPreparedMarkdownImageUrl(preparation, directory), status: 'loading' });
+      return;
+    }
     const controller = new AbortController();
     setImage({ url: '', status: 'loading' });
-    void resolveMarkdownImageSource(candidate.source, directory, controller.signal)
-      .then((url) => {
-        if (!controller.signal.aborted) setImage({ url, status: 'loading' });
-      })
-      .catch(() => {
-        if (!controller.signal.aborted) setImage({ url: '', status: 'error' });
-      });
+    void resolveMarkdownImageSource(candidate.source, controller.signal).then((url) => {
+      if (controller.signal.aborted) return;
+      setImage({ url, status: 'loading' });
+    }).catch(() => {
+      if (controller.signal.aborted) return;
+      setImage({ url: '', status: 'error' });
+    });
     return () => controller.abort();
-  }, [candidate.source, directory, shouldLoad]);
+  }, [assetAuthNonce, assetAuthReady, candidate.source, directory, local, preparation, shouldLoad]);
 
   const openPreview = React.useCallback(() => {
+    if (image.status === 'error') {
+      toast.error(t('filesView.error.previewUnavailable'));
+      return;
+    }
     if (image.status !== 'ready' || !onShowPopup) return;
     onShowPopup({
       open: true,
@@ -61,7 +129,7 @@ const MarkdownImageThumbnail: React.FC<{
       metadata: { tool: 'markdown-image-preview', filename: candidate.filename },
       image: { url: image.url, filename: candidate.filename },
     });
-  }, [candidate.filename, image, onShowPopup]);
+  }, [candidate.filename, image, onShowPopup, t]);
 
   return (
     <button
@@ -69,7 +137,7 @@ const MarkdownImageThumbnail: React.FC<{
       type="button"
       className="w-[100px] shrink-0 text-left outline-none focus-visible:ring-2 focus-visible:ring-[var(--interactive-focus-ring)]"
       aria-label={candidate.filename}
-      disabled={image.status !== 'ready'}
+      disabled={image.status === 'loading'}
       onClick={openPreview}
       data-openchamber-markdown-image-action="true"
       data-openchamber-markdown-image-source={candidate.source}
@@ -107,27 +175,88 @@ const MarkdownImageThumbnail: React.FC<{
 };
 
 export const MarkdownImageGallery: React.FC<{
+  sessionId?: string;
+  messageId: string;
   contents: readonly string[];
   onShowPopup?: (content: ToolPopupContent) => void;
-}> = ({ contents, onShowPopup }) => {
+}> = ({ sessionId, messageId, contents, onShowPopup }) => {
   const directory = useEffectiveDirectory() ?? '';
+  const galleryRef = React.useRef<HTMLDivElement>(null);
+  const [shouldPrepare, setShouldPrepare] = React.useState(false);
+  const [prepared, setPrepared] = React.useState<Map<string, PreparedMarkdownImage> | null>(null);
+  const [prepareEpoch, setPrepareEpoch] = React.useState(0);
   const candidates = React.useMemo(
     () => extractMarkdownImageCandidates(contents, MAX_MARKDOWN_IMAGE_COUNT),
     [contents],
   );
+  const localSources = React.useMemo(
+    () => candidates.filter((candidate) => isLocalMarkdownImageSource(candidate.source)).map((candidate) => candidate.source),
+    [candidates],
+  );
+  React.useEffect(() => {
+    if (localSources.length === 0 || shouldPrepare) return;
+    const gallery = galleryRef.current;
+    if (!gallery || typeof IntersectionObserver === 'undefined') {
+      setShouldPrepare(true);
+      return;
+    }
+    const observer = new IntersectionObserver((entries) => {
+      if (!entries.some((entry) => entry.isIntersecting)) return;
+      setShouldPrepare(true);
+      observer.disconnect();
+    }, { rootMargin: '200px' });
+    observer.observe(gallery);
+    return () => observer.disconnect();
+  }, [localSources.length, shouldPrepare]);
 
-  if (candidates.length === 0) return null;
+  React.useEffect(() => {
+    if (!shouldPrepare || !sessionId || localSources.length === 0) return;
+    const controller = new AbortController();
+    void prepareLocalMarkdownImages({
+      sources: localSources,
+      directory,
+      sessionId,
+      messageId,
+      signal: controller.signal,
+    }).then((result) => {
+      if (controller.signal.aborted) return;
+      setPrepared(result);
+    }).catch(() => {
+      if (!controller.signal.aborted) {
+        setPrepared(new Map(localSources.map((source) => [source, { status: 'error' }])));
+      }
+    });
+    return () => controller.abort();
+  }, [directory, localSources, messageId, prepareEpoch, sessionId, shouldPrepare]);
+
+  React.useEffect(() => {
+    const nextExpiry = Math.min(...[...(prepared?.values() ?? [])]
+      .filter((value): value is Extract<PreparedMarkdownImage, { status: 'ready' }> => value.status === 'ready')
+      .map((value) => value.expiresAt ?? Number.POSITIVE_INFINITY));
+    if (!Number.isFinite(nextExpiry)) return;
+    const timer = setTimeout(() => setPrepareEpoch((current) => current + 1), Math.max(0, nextExpiry - Date.now()));
+    return () => clearTimeout(timer);
+  }, [prepared]);
+
+  const visibleCandidates = candidates.filter((candidate) => prepared?.get(candidate.source)?.status !== 'missing');
+  const hasPreparedAssets = [...(prepared?.values() ?? [])].some((value) => value.status === 'ready');
+  const assetAuth = useAssetAuth(hasPreparedAssets);
+  if (visibleCandidates.length === 0) return null;
 
   return (
     <div
+      ref={galleryRef}
       className="mt-3 flex max-w-full gap-2 overflow-x-auto pb-1"
       data-openchamber-markdown-image-gallery="true"
     >
-      {candidates.map((candidate) => (
+      {visibleCandidates.map((candidate) => (
         <MarkdownImageThumbnail
           key={candidate.source}
           candidate={candidate}
+          preparation={prepared?.get(candidate.source)}
           directory={directory}
+          assetAuthReady={assetAuth.ready}
+          assetAuthNonce={assetAuth.nonce}
           onShowPopup={onShowPopup}
         />
       ))}
diff --git a/packages/ui/src/components/chat/MarkdownRendererImpl.tsx b/packages/ui/src/components/chat/MarkdownRendererImpl.tsx
index d38ebf57..69690752 100644
--- a/packages/ui/src/components/chat/MarkdownRendererImpl.tsx
+++ b/packages/ui/src/components/chat/MarkdownRendererImpl.tsx
@@ -19,8 +19,7 @@ import { isDesktopLocalOriginActive, isDesktopShell, isVSCodeRuntime } from '@/l
 import { isMobileSurfaceRuntime } from '@/lib/runtimeSurface';
 import { ensureOutsideFileGrantForDesktop } from '@/lib/outsideFileGrants';
 import { getDirectoryForFilePath, isFilePathWithinDirectory, toAbsoluteFilePath } from '@/lib/path-utils';
-import { getMarkdownImageFilename, renderMarkdownBlocks, renderMarkdownSync } from './markdown/markdownCore';
-import { resolveMarkdownImageSource } from './markdown/markdownImageAssets';
+import { renderMarkdownBlocks, renderMarkdownSync, type MarkdownImageMode } from './markdown/markdownCore';
 import { ensureMarkdownShikiTheme } from './markdown/markdownTheme';
 import { getMarkdownSyntaxVars } from './markdown/markdownSyntaxVars';
 import {
@@ -109,59 +108,6 @@ const useExternalLinkInteractions = ({
   }, [containerRef, enabled]);
 };
 
-const useMarkdownImageLinkInteractions = ({
-  containerRef,
-  directory,
-  enabled,
-  onShowPopup,
-}: {
-  containerRef: React.RefObject<HTMLDivElement | null>;
-  directory: string;
-  enabled: boolean;
-  onShowPopup?: (content: ToolPopupContent) => void;
-}) => {
-  React.useEffect(() => {
-    const container = containerRef.current;
-    if (!enabled || !container || !onShowPopup) return;
-
-    const controller = new AbortController();
-    const handleClick = (event: MouseEvent) => {
-      if (event.defaultPrevented || event.button !== 0) return;
-      const target = event.target;
-      if (!(target instanceof Element)) return;
-
-      const link = target.closest<HTMLAnchorElement>('[data-openchamber-markdown-image-link="true"]');
-      if (!link || !container.contains(link)) return;
-
-      const source = link.getAttribute('data-openchamber-markdown-image-source') ?? '';
-      const filename = link.getAttribute('data-openchamber-markdown-image-filename')
-        || getMarkdownImageFilename(source, '');
-      if (!source || !filename) return;
-
-      event.preventDefault();
-      event.stopPropagation();
-      void resolveMarkdownImageSource(source, directory, controller.signal)
-        .then((url) => {
-          if (controller.signal.aborted || !link.isConnected) return;
-          onShowPopup({
-            open: true,
-            title: filename,
-            content: '',
-            metadata: { tool: 'markdown-image-preview', filename },
-            image: { url, filename },
-          });
-        })
-        .catch(() => undefined);
-    };
-
-    container.addEventListener('click', handleClick);
-    return () => {
-      controller.abort();
-      container.removeEventListener('click', handleClick);
-    };
-  }, [containerRef, directory, enabled, onShowPopup]);
-};
-
 const DEFAULT_MERMAID_CONTROLS: MermaidControlOptions = {
   download: true,
   copy: true,
@@ -195,7 +141,6 @@ interface MarkdownRendererProps {
   variant?: MarkdownVariant;
   onShowPopup?: (content: ToolPopupContent) => void;
   enableFileReferences?: boolean;
-  enableLocalImages?: boolean;
 }
 
 const FILE_LINK_SELECTOR = '[data-openchamber-file-link="true"]';
@@ -557,10 +502,6 @@ const useFileReferenceInteractions = ({
       let linkedCount = 0;
 
       for (const candidate of Array.from(candidates)) {
-        if (candidate.matches('[data-openchamber-markdown-image-link="true"]')) {
-          clearFileLinkAttributes(candidate);
-          continue;
-        }
         const rawCandidate = extractPathCandidateFromElement(candidate);
         const resolved = getResolvedReference(rawCandidate, effectiveDirectory);
         clearFileLinkAttributes(candidate);
@@ -895,7 +836,7 @@ const useMorphdomMarkdown = ({
   text,
   streaming,
   cacheKey,
-  deferImages = false,
+  imageMode = 'inline',
   syntaxVars,
   ctx,
 }: {
@@ -903,7 +844,7 @@ const useMorphdomMarkdown = ({
   text: string;
   streaming: boolean;
   cacheKey: string;
-  deferImages?: boolean;
+  imageMode?: MarkdownImageMode;
   syntaxVars: Record<string, string>;
   ctx: DecorateContext;
 }) => {
@@ -942,7 +883,7 @@ const useMorphdomMarkdown = ({
       // `display:contents` keeps margin-collapsing/spacing identical to a flat
       // HTML body — the wrapper exists only for per-block reconciliation.
       block.style.display = 'contents';
-      block.innerHTML = renderMarkdownSync(text, deferImages);
+      block.innerHTML = renderMarkdownSync(text, imageMode);
       // Decorate synchronously too: wrap code blocks in their framed card,
       // mark inline code, build table controls, etc. The async pass re-decorates
       // its own DOM before morphing, so without this the first paint shows bare
@@ -954,7 +895,7 @@ const useMorphdomMarkdown = ({
         refreshMermaidViewers();
       }
     }
-  }, [containerRef, text, deferImages, ctx, refreshMermaidViewers]);
+  }, [containerRef, text, imageMode, ctx, refreshMermaidViewers]);
 
   React.useEffect(() => () => {
     mermaidViewerRef.current?.cleanup();
@@ -967,7 +908,7 @@ const useMorphdomMarkdown = ({
     const target = container.querySelector<HTMLElement>('[data-markdown-content]') ?? container;
     let active = true;
 
-    void renderMarkdownBlocks(text, streaming, cacheKey, deferImages).then((blocks) => {
+    void renderMarkdownBlocks(text, streaming, cacheKey, imageMode).then((blocks) => {
       if (!active) return;
       const existing = Array.from(target.children) as HTMLElement[];
 
@@ -1018,7 +959,7 @@ const useMorphdomMarkdown = ({
     return () => {
       active = false;
     };
-  }, [containerRef, text, streaming, cacheKey, deferImages, ctx, refreshMermaidViewers]);
+  }, [containerRef, text, streaming, cacheKey, imageMode, ctx, refreshMermaidViewers]);
 
   React.useEffect(() => {
     const container = containerRef.current;
@@ -1065,7 +1006,6 @@ const MarkdownRendererImpl: React.FC<MarkdownRendererProps> = ({
   variant = 'assistant',
   onShowPopup,
   enableFileReferences = true,
-  enableLocalImages = false,
 }) => {
   streamPerfCount('ui.markdown_renderer.render');
   if (isStreaming) streamPerfCount('ui.markdown_renderer.render.streaming');
@@ -1097,12 +1037,6 @@ const MarkdownRendererImpl: React.FC<MarkdownRendererProps> = ({
     enabled: enableFileReferences && !isStreaming,
   });
   useExternalLinkInteractions({ containerRef });
-  useMarkdownImageLinkInteractions({
-    containerRef,
-    directory: effectiveDirectory,
-    enabled: enableLocalImages && variant === 'assistant' && !isStreaming,
-    onShowPopup,
-  });
 
   const syntaxVars = React.useMemo(() => getMarkdownSyntaxVars(currentTheme), [currentTheme]);
   const ctx = useDecorateContext(currentTheme, live, effectiveDirectory ? handlePreviewLoopback : undefined, DEFAULT_MERMAID_CONTROLS);
@@ -1113,17 +1047,13 @@ const MarkdownRendererImpl: React.FC<MarkdownRendererProps> = ({
     text: content,
     streaming: live,
     cacheKey,
-    deferImages: enableLocalImages && variant === 'assistant' && !isStreaming,
+    imageMode: variant === 'assistant' ? 'label' : 'inline',
     syntaxVars,
     ctx,
   });
 
   const markdownContent = (
-    <div
-      className={cn('break-words w-full min-w-0', className)}
-      ref={containerRef}
-      data-openchamber-finalized-assistant-images={enableLocalImages && variant === 'assistant' && !isStreaming ? 'true' : undefined}
-    >
+    <div className={cn('break-words w-full min-w-0', className)} ref={containerRef}>
       <div className={markdownContentClassName(variant)} data-markdown-content />
     </div>
   );
@@ -1150,7 +1080,6 @@ export const MarkdownRenderer = React.memo(MarkdownRendererImpl, (prev, next) =>
     && prev.messageId === next.messageId
     && prev.onShowPopup === next.onShowPopup
     && prev.enableFileReferences === next.enableFileReferences
-    && prev.enableLocalImages === next.enableLocalImages
     && prev.part?.id === next.part?.id;
 });
 
diff --git a/packages/ui/src/components/chat/markdown/decorate.ts b/packages/ui/src/components/chat/markdown/decorate.ts
index 51efc32c..6dba0f2b 100644
--- a/packages/ui/src/components/chat/markdown/decorate.ts
+++ b/packages/ui/src/components/chat/markdown/decorate.ts
@@ -57,6 +57,7 @@ const ICONS = {
   zoomOut: spriteIcon('subtract'),
   fit: spriteIcon('refresh'),
   textWrap: spriteIcon('text-wrap'),
+  image: spriteIcon('file-image'),
 } as const;
 
 const ICON_BTN_CLASS =
@@ -66,6 +67,18 @@ const setIconHtml = (el: Element, html: string): void => {
   el.innerHTML = html;
 };
 
+const decorateImageLabels = (root: HTMLElement): void => {
+  for (const label of Array.from(root.querySelectorAll<HTMLElement>('[data-openchamber-markdown-image-label="true"]'))) {
+    if (label.querySelector('[data-openchamber-markdown-image-label-icon]')) continue;
+    const icon = document.createElement('span');
+    icon.className = 'inline-flex shrink-0';
+    icon.setAttribute('aria-hidden', 'true');
+    icon.setAttribute('data-openchamber-markdown-image-label-icon', 'true');
+    setIconHtml(icon, ICONS.image);
+    label.prepend(icon);
+  }
+};
+
 const makeIconButton = (icon: keyof typeof ICONS, title: string, slot: string): HTMLButtonElement => {
   const button = document.createElement('button');
   button.type = 'button';
@@ -487,6 +500,7 @@ const decorateLinks = (root: HTMLElement, ctx: DecorateContext): void => {
 
 /** Run all idempotent DOM decoration passes over freshly-rendered markdown. */
 export const decorateMarkdown = (root: HTMLElement, ctx: DecorateContext): void => {
+  decorateImageLabels(root);
   decorateInlineCode(root);
   decorateMermaid(root, ctx);
   decorateCodeBlocks(root, ctx);
diff --git a/packages/ui/src/components/chat/markdown/markdownCore.test.ts b/packages/ui/src/components/chat/markdown/markdownCore.test.ts
index 2b8b31b1..968363d3 100644
--- a/packages/ui/src/components/chat/markdown/markdownCore.test.ts
+++ b/packages/ui/src/components/chat/markdown/markdownCore.test.ts
@@ -13,7 +13,11 @@ mock.module('./markdown-worker', () => ({
 
 import { escapeRawMarkdownHtml, isLocalFileUrl, MARKDOWN_FORBIDDEN_TAGS } from './markdownSecurity';
 
-const { extractMarkdownImageCandidates, renderMarkdownSync } = await import('./markdownCore');
+const {
+  __markdownImageCandidateCacheForTests,
+  extractMarkdownImageCandidates,
+  renderMarkdownSync,
+} = await import('./markdownCore');
 const { resolveMarkdownImageSource } = await import('./markdownImageAssets');
 
 describe('markdown sanitization', () => {
@@ -39,45 +43,31 @@ describe('markdown sanitization', () => {
 });
 
 describe('Markdown images', () => {
-  test('keeps local image links in text and emits inert image placeholders', () => {
+  test('renders assistant images as icon-ready text without loading the source', () => {
     const html = renderMarkdownSync([
       '[linked image](packages/vscode/extension.jpg)',
       '![image syntax](packages/vscode/extension.jpg)',
-    ].join('\n\n'), true);
+    ].join('\n\n'), 'label');
 
-    expect(html).toContain('data-openchamber-markdown-image-link="true"');
-    expect(html.match(/data-openchamber-markdown-image-source="packages\/vscode\/extension.jpg"/g)).toHaveLength(1);
-    expect(html).toContain('data-openchamber-markdown-image-placeholder="true"');
-    expect(html).toContain('image syntax');
-    expect(html).not.toContain('src="packages/vscode/extension.jpg"');
-    expect(html).not.toContain('data-openchamber-markdown-image-state');
+    expect(html).toContain('data-openchamber-markdown-image-label="true"');
+    expect(html).toContain('extension.jpg');
+    expect(html).not.toContain('image syntax');
+    expect(html).not.toContain('<img');
     expect(html.match(/<a /g)).toHaveLength(1);
   });
 
-  test('keeps HTTP links as links and defers remote image tokens to finalized rendering', () => {
+  test('keeps non-chat Markdown images inline', () => {
     const html = renderMarkdownSync([
       '[remote link](https://example.test/image.png)',
       '![remote image](https://example.test/image.png)',
-    ].join('\n\n'), true);
+    ].join('\n\n'));
 
     expect(html).toContain('<a href="https://example.test/image.png"');
-    expect(html).not.toContain('<img');
-    expect(html).toContain('data-openchamber-markdown-image-placeholder="true"');
-    expect(html).toContain('remote image');
+    expect(html).toContain('<img src="https://example.test/image.png" alt="remote image">');
+    expect(html).not.toContain('data-openchamber-markdown-image-label');
   });
 
-  test('preserves file URLs inertly and never activates unknown schemes', () => {
-    const html = renderMarkdownSync([
-      '![file](file:///workspace/image.png)',
-      '![unsafe](javascript:alert(1))',
-    ].join('\n\n'), true);
-
-    expect(html).toContain('role="img"');
-    expect(html).not.toContain('src="file:');
-    expect(html).not.toContain('src="javascript:');
-  });
-
-  test('collects a single ordered gallery across mixed Markdown and ignores code', () => {
+  test('collects image syntax across mixed Markdown and ignores links and code', () => {
     const candidates = extractMarkdownImageCandidates([
       [
         'Before [local link](screens/first%20view.png) and `![code](ignored.png)`.',
@@ -99,6 +89,10 @@ describe('Markdown images', () => {
     ]);
   });
 
+  test('does not add an ordinary local image link to the gallery', () => {
+    expect(extractMarkdownImageCandidates(['[download](screens/image.png)'])).toEqual([]);
+  });
+
   test('limits one finalized message gallery to twelve unique candidates', () => {
     const markdown = Array.from({ length: 14 }, (_, index) => `![image ${index}](screens/${index}.png)`).join('\n');
 
@@ -108,12 +102,69 @@ describe('Markdown images', () => {
     expect(candidates.at(-1)?.source).toBe('screens/11.png');
   });
 
+  test('reuses extracted candidates across virtualized remounts without changing gallery behavior', () => {
+    __markdownImageCandidateCacheForTests.reset();
+    const contents = Array.from({ length: 20 }, (_, index) => `![image ${index}](screens/${index}.png)`);
+
+    expect(extractMarkdownImageCandidates(contents)).toHaveLength(12);
+    expect(__markdownImageCandidateCacheForTests.stats().scans).toBe(12);
+
+    for (let round = 0; round < 1000; round += 1) {
+      expect(extractMarkdownImageCandidates(contents)).toHaveLength(12);
+    }
+
+    const stats = __markdownImageCandidateCacheForTests.stats();
+    expect(stats.entries).toBe(12);
+    expect(stats.scans).toBe(12);
+  });
+
+  test('scans one thousand independent messages once across virtualized remounts', () => {
+    __markdownImageCandidateCacheForTests.reset();
+    const messages = Array.from(
+      { length: 1000 },
+      (_, index) => `![image ${index}](screens/${index}.png)`,
+    );
+
+    for (const message of messages) extractMarkdownImageCandidates([message]);
+    for (const message of messages) extractMarkdownImageCandidates([message]);
+
+    const stats = __markdownImageCandidateCacheForTests.stats();
+    expect(stats.entries).toBe(1000);
+    expect(stats.scans).toBe(1000);
+  });
+
+  test('gives embedded images without alt text a stable filename', () => {
+    const source = 'data:image/png;base64,AAAA';
+
+    expect(extractMarkdownImageCandidates([`![](${source})`])).toEqual([
+      { source, filename: 'image.png' },
+    ]);
+    expect(renderMarkdownSync(`![](${source})`, 'label')).toContain('image.png');
+  });
+
+  test('bounds cached candidate entries and bytes, and skips oversized individual content', () => {
+    __markdownImageCandidateCacheForTests.reset();
+    for (let index = 0; index < 1025; index += 1) {
+      extractMarkdownImageCandidates([`![image ${index}](screens/${index}.png)`]);
+    }
+    const boundedStats = __markdownImageCandidateCacheForTests.stats();
+    expect(boundedStats.entries).toBe(1024);
+    expect(boundedStats.bytes <= 2 * 1024 * 1024).toBe(true);
+
+    __markdownImageCandidateCacheForTests.reset();
+    const oversized = `![image](screens/large.png)\n${'x'.repeat(64 * 1024)}`;
+
+    extractMarkdownImageCandidates([oversized]);
+    extractMarkdownImageCandidates([oversized]);
+    expect(__markdownImageCandidateCacheForTests.stats()).toEqual({ entries: 0, bytes: 0, scans: 2 });
+  });
+
   test('validates embedded image bytes against the declared MIME type', async () => {
     const png = 'iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUlEQVR42mP8z8DwHwAFBQIAX8jx0gAAAABJRU5ErkJggg==';
     const signal = new AbortController().signal;
 
-    expect(await resolveMarkdownImageSource(`data:image/png;base64,${png}`, '', signal)).toBe(`data:image/png;base64,${png}`);
-    await resolveMarkdownImageSource(`data:image/jpeg;base64,${png}`, '', signal).then(
+    expect(await resolveMarkdownImageSource(`data:image/png;base64,${png}`, signal)).toBe(`data:image/png;base64,${png}`);
+    await resolveMarkdownImageSource(`data:image/jpeg;base64,${png}`, signal).then(
       () => { throw new Error('Expected mismatched image data to fail'); },
       (error: unknown) => expect((error as Error).message).toBe('Unsupported image data'),
     );
@@ -123,7 +174,7 @@ describe('Markdown images', () => {
     const controller = new AbortController();
     controller.abort();
 
-    await resolveMarkdownImageSource('https://example.test/image.png', '', controller.signal).then(
+    await resolveMarkdownImageSource('https://example.test/image.png', controller.signal).then(
       () => { throw new Error('Expected an aborted image load to fail'); },
       (error: unknown) => expect((error as Error).name).toBe('AbortError'),
     );
@@ -133,6 +184,6 @@ describe('Markdown images', () => {
     const html = renderMarkdownSync('![tool image](https://example.test/image.png)');
 
     expect(html).toContain('<img src="https://example.test/image.png"');
-    expect(html).not.toContain('data-openchamber-markdown-image-placeholder');
+    expect(html).not.toContain('data-openchamber-markdown-image');
   });
 });
diff --git a/packages/ui/src/components/chat/markdown/markdownCore.ts b/packages/ui/src/components/chat/markdown/markdownCore.ts
index 95b18b6d..c82c2218 100644
--- a/packages/ui/src/components/chat/markdown/markdownCore.ts
+++ b/packages/ui/src/components/chat/markdown/markdownCore.ts
@@ -19,8 +19,23 @@ export interface MarkdownImageCandidate {
   filename: string;
 }
 
+export type MarkdownImageMode = 'inline' | 'label';
+
 export const MAX_MARKDOWN_IMAGE_COUNT = 12;
 
+const MARKDOWN_IMAGE_CANDIDATE_CACHE_MAX_ENTRIES = 1024;
+const MARKDOWN_IMAGE_CANDIDATE_CACHE_MAX_BYTES = 2 * 1024 * 1024;
+const MARKDOWN_IMAGE_CANDIDATE_CACHE_MAX_ENTRY_BYTES = 64 * 1024;
+
+type MarkdownImageCandidateCacheEntry = {
+  candidates: MarkdownImageCandidate[];
+  bytes: number;
+};
+
+const markdownImageCandidateCache = new Map<string, MarkdownImageCandidateCacheEntry>();
+let markdownImageCandidateCacheBytes = 0;
+let markdownImageCandidateScanCount = 0;
+
 const isLocalMarkdownImageSource = (source: string): boolean => {
   if (/^\/\//.test(source) || !LOCAL_IMAGE_EXTENSION_RE.test(source)) return false;
   return WINDOWS_ABSOLUTE_PATH_RE.test(source)
@@ -34,8 +49,11 @@ const isSupportedMarkdownImageSource = (source: string): boolean => (
   || isLocalMarkdownImageSource(source)
 );
 
-export const getMarkdownImageFilename = (source: string, fallback: string): string => {
-  if (/^data:/i.test(source)) return fallback.trim();
+const getMarkdownImageFilename = (source: string, fallback: string): string => {
+  if (/^data:image\/(png|jpeg|gif|webp)/i.test(source)) {
+    const extension = /^data:image\/([^;,]+)/i.exec(source)?.[1]?.replace('jpeg', 'jpg') ?? 'png';
+    return fallback.trim() || `image.${extension}`;
+  }
 
   const path = source.split(/[?#]/, 1)[0]?.replace(/\\/g, '/') ?? '';
   const encodedName = path.split('/').filter(Boolean).at(-1) ?? '';
@@ -47,6 +65,87 @@ export const getMarkdownImageFilename = (source: string, fallback: string): stri
   }
 };
 
+const estimateMarkdownImageCandidateCacheEntryBytes = (
+  markdown: string,
+  candidates: readonly MarkdownImageCandidate[],
+): number => (
+  (markdown.length + candidates.reduce((total, candidate) => total + candidate.source.length + candidate.filename.length, 0)) * 2
+);
+
+const scanMarkdownImageCandidates = (markdown: string): MarkdownImageCandidate[] => {
+  markdownImageCandidateScanCount += 1;
+  const candidates: MarkdownImageCandidate[] = [];
+  const seen = new Set<string>();
+  const tokens = marked.lexer(markdown);
+  marked.walkTokens(tokens, (token) => {
+    if (token.type !== 'image') return;
+
+    const source = token.href ?? '';
+    if (!source || !isSupportedMarkdownImageSource(source) || seen.has(source)) return;
+    const fallback = typeof token.text === 'string' ? token.text : '';
+    const filename = getMarkdownImageFilename(source, fallback);
+    if (!filename) return;
+
+    seen.add(source);
+    candidates.push({ source, filename });
+  });
+  return candidates;
+};
+
+const getMarkdownImageCandidates = (markdown: string): MarkdownImageCandidate[] => {
+  const cached = markdownImageCandidateCache.get(markdown);
+  if (cached) {
+    markdownImageCandidateCache.delete(markdown);
+    markdownImageCandidateCache.set(markdown, cached);
+    return cached.candidates;
+  }
+
+  const candidates = scanMarkdownImageCandidates(markdown);
+  const bytes = estimateMarkdownImageCandidateCacheEntryBytes(markdown, candidates);
+  if (bytes > MARKDOWN_IMAGE_CANDIDATE_CACHE_MAX_ENTRY_BYTES) return candidates;
+
+  while (
+    markdownImageCandidateCache.size >= MARKDOWN_IMAGE_CANDIDATE_CACHE_MAX_ENTRIES
+    || markdownImageCandidateCacheBytes + bytes > MARKDOWN_IMAGE_CANDIDATE_CACHE_MAX_BYTES
+  ) {
+    const oldest = markdownImageCandidateCache.entries().next().value;
+    if (!oldest) break;
+    markdownImageCandidateCache.delete(oldest[0]);
+    markdownImageCandidateCacheBytes -= oldest[1].bytes;
+  }
+  markdownImageCandidateCache.set(markdown, { candidates, bytes });
+  markdownImageCandidateCacheBytes += bytes;
+  return candidates;
+};
+
+/** @internal Test-only cache instrumentation for deterministic regression tests. */
+export const __markdownImageCandidateCacheForTests = {
+  reset: (): void => {
+    markdownImageCandidateCache.clear();
+    markdownImageCandidateCacheBytes = 0;
+    markdownImageCandidateScanCount = 0;
+  },
+  stats: () => ({
+    entries: markdownImageCandidateCache.size,
+    bytes: markdownImageCandidateCacheBytes,
+    scans: markdownImageCandidateScanCount,
+  }),
+};
+
+const renderMarkdownImageLabel = ({
+  href,
+  title,
+  text,
+}: {
+  href: string;
+  title?: string | null;
+  text: string;
+}): string => {
+  const label = getMarkdownImageFilename(href ?? '', text);
+  const titleAttr = title ? ` title="${escapeAttr(title)}"` : '';
+  return `<span${titleAttr} class="inline-flex items-center gap-1 align-text-bottom text-muted-foreground" data-openchamber-markdown-image-label="true">${escapeAttr(label)}</span>`;
+};
+
 export const extractMarkdownImageCandidates = (
   markdownTexts: readonly string[],
   limit = MAX_MARKDOWN_IMAGE_COUNT,
@@ -58,47 +157,17 @@ export const extractMarkdownImageCandidates = (
 
   for (const markdown of markdownTexts) {
     if (!markdown || candidates.length >= limit) continue;
-    const tokens = marked.lexer(markdown);
-    marked.walkTokens(tokens, (token) => {
-      if (candidates.length >= limit) return;
-
-      if (token.type !== 'image' && token.type !== 'link') return;
-      if (token.type === 'link' && !isLocalMarkdownImageSource(token.href ?? '')) return;
-
-      const source = token.href ?? '';
-      if (!source || !isSupportedMarkdownImageSource(source) || seen.has(source)) return;
-      const fallback = typeof token.text === 'string' ? token.text : '';
-      const filename = getMarkdownImageFilename(source, fallback);
-      if (!filename) return;
-
-      seen.add(source);
-      candidates.push({ source, filename });
-    });
+    for (const candidate of getMarkdownImageCandidates(markdown)) {
+      if (candidates.length >= limit) break;
+      if (seen.has(candidate.source)) continue;
+      seen.add(candidate.source);
+      candidates.push({ ...candidate });
+    }
   }
 
   return candidates;
 };
 
-const renderMarkdownImage = ({
-  href,
-  title,
-  text,
-}: {
-  href: string;
-  title?: string | null;
-  text: string;
-}): string => {
-  const source = href ?? '';
-  const alt = escapeAttr(text ?? '');
-  const titleAttr = title ? ` title="${escapeAttr(title)}"` : '';
-  const supported = isSupportedMarkdownImageSource(source);
-  if (!supported) {
-    return `<span role="img" aria-label="${alt}"${titleAttr}>${alt}</span>`;
-  }
-
-  return `<span role="img" aria-label="${alt}"${titleAttr} data-openchamber-markdown-image-placeholder="true">${alt}</span>`;
-};
-
 // ---------------------------------------------------------------------------
 // Streaming block segmentation (port of OpenCode's markdown-stream)
 // ---------------------------------------------------------------------------
@@ -251,7 +320,7 @@ const blockMathExtension = {
   },
 };
 
-const createParser = (deferImages: boolean) => new Marked().use({
+const createParser = (imageMode: MarkdownImageMode) => new Marked().use({
   gfm: true,
   breaks: false,
   extensions: [inlineMathExtension, blockMathExtension],
@@ -264,11 +333,6 @@ const createParser = (deferImages: boolean) => new Marked().use({
     },
     link({ href, title, text }) {
       const target = href ?? '';
-      if (deferImages && isLocalMarkdownImageSource(target)) {
-        const titleAttr = title ? ` title="${escapeAttr(title)}"` : '';
-        const filename = getMarkdownImageFilename(target, '');
-        return `<a href="${escapeAttr(target)}"${titleAttr} class="external-link" target="_blank" rel="noopener noreferrer" data-openchamber-markdown-image-link="true" data-openchamber-markdown-image-source="${escapeAttr(target)}" data-openchamber-markdown-image-filename="${escapeAttr(filename)}">${text}</a>`;
-      }
       const agentName = parseAgentHref(target);
       if (agentName) {
         return `<a href="${escapeAttr(buildAgentMentionUrl(agentName))}" data-openchamber-agent-mention="true" class="text-primary hover:underline" target="_blank" rel="noopener noreferrer">${text}</a>`;
@@ -280,12 +344,12 @@ const createParser = (deferImages: boolean) => new Marked().use({
       const titleAttr = title ? ` title="${escapeAttr(title)}"` : '';
       return `<a href="${escapeAttr(target)}"${titleAttr} class="external-link" target="_blank" rel="noopener noreferrer">${text}</a>`;
     },
-    ...(deferImages ? { image: renderMarkdownImage } : {}),
+    ...(imageMode === 'label' ? { image: renderMarkdownImageLabel } : {}),
   },
 });
 
-const parser = createParser(false);
-const imageParser = createParser(true);
+const inlineImageParser = createParser('inline');
+const imageLabelParser = createParser('label');
 
 // ---------------------------------------------------------------------------
 // Math (KaTeX) — post-process the parsed HTML, skipping code/pre/kbd content
@@ -443,8 +507,9 @@ const touch = (key: string, entry: { hash: string; html: string }): void => {
   if (oldest) htmlCache.delete(oldest);
 };
 
-const parseBlock = async (block: MarkdownBlock, deferImages: boolean): Promise<string> => {
-  const parsed = await Promise.resolve((deferImages ? imageParser : parser).parse(block.src));
+const parseBlock = async (block: MarkdownBlock, imageMode: MarkdownImageMode): Promise<string> => {
+  const parser = imageMode === 'label' ? imageLabelParser : inlineImageParser;
+  const parsed = await Promise.resolve(parser.parse(block.src));
   const withMath = renderMathExpressions(parsed);
   const highlighted = block.highlight ? await highlightCodeBlocks(withMath) : withMath;
   return sanitize(highlighted);
@@ -459,9 +524,10 @@ const parseBlock = async (block: MarkdownBlock, deferImages: boolean): Promise<s
  * is synchronous (marked is not configured `async`), so this never blocks on a
  * worker round-trip.
  */
-export const renderMarkdownSync = (text: string, deferImages = false): string => {
+export const renderMarkdownSync = (text: string, imageMode: MarkdownImageMode = 'inline'): string => {
   if (!text) return '';
-  const parsed = (deferImages ? imageParser : parser).parse(text) as string;
+  const parser = imageMode === 'label' ? imageLabelParser : inlineImageParser;
+  const parsed = parser.parse(text) as string;
   const withMath = renderMathExpressions(parsed);
   return sanitize(withMath);
 };
@@ -484,7 +550,7 @@ export const renderMarkdownBlocks = async (
   text: string,
   streaming: boolean,
   cacheKey: string,
-  deferImages = false,
+  imageMode: MarkdownImageMode = 'inline',
 ): Promise<RenderedBlock[]> => {
   if (!text) return [];
 
@@ -492,14 +558,14 @@ export const renderMarkdownBlocks = async (
   return Promise.all(
     blocks.map(async (block, index) => {
       const contentHash = hash(block.raw);
-      const id = `${contentHash}:${block.mode}:${block.highlight ? 1 : 0}:${deferImages ? 1 : 0}`;
-      const key = `${cacheKey}:${index}:${block.mode}:${deferImages ? 1 : 0}`;
+      const id = `${contentHash}:${block.mode}:${block.highlight ? 1 : 0}:${imageMode}`;
+      const key = `${cacheKey}:${index}:${block.mode}:${imageMode}`;
       const cached = htmlCache.get(key);
       if (cached && cached.hash === contentHash) {
         touch(key, cached);
         return { id, html: cached.html };
       }
-      const html = await parseBlock(block, deferImages);
+      const html = await parseBlock(block, imageMode);
       touch(key, { hash: contentHash, html });
       return { id, html };
     }),
diff --git a/packages/ui/src/components/chat/markdown/markdownImageAssets.test.ts b/packages/ui/src/components/chat/markdown/markdownImageAssets.test.ts
new file mode 100644
index 00000000..72c5ea3f
--- /dev/null
+++ b/packages/ui/src/components/chat/markdown/markdownImageAssets.test.ts
@@ -0,0 +1,68 @@
+import { describe, expect, mock, test } from 'bun:test';
+
+let requestCount = 0;
+const runtimeFetch = mock(async (_path: string, init?: RequestInit) => {
+  requestCount += 1;
+  const body = JSON.parse(String(init?.body)) as { sources: string[] };
+  return new Response(JSON.stringify({
+    results: body.sources.map((source) => ({ source, status: 'ready', path: `/repo/${source}` })),
+  }), { status: 200, headers: { 'content-type': 'application/json' } });
+});
+const resolver = {
+  api: () => '',
+  authenticatedAsset: (path: string, query: Record<string, string | undefined>) => {
+    const params = new URLSearchParams(Object.entries(query).filter((entry): entry is [string, string] => Boolean(entry[1])));
+    return `${path}?${params}`;
+  },
+};
+
+mock.module('@/lib/runtime-fetch', () => ({ runtimeFetch }));
+mock.module('@/lib/runtime-url', () => ({ getRuntimeUrlResolver: () => resolver }));
+
+const { getPreparedMarkdownImageUrl, prepareLocalMarkdownImages } = await import('./markdownImageAssets');
+
+describe('Markdown image asset preparation', () => {
+  test('prepares many images in one message-level request', async () => {
+    requestCount = 0;
+    const sources = Array.from({ length: 12 }, (_, index) => `${index}.png`);
+
+    const result = await prepareLocalMarkdownImages({
+      sources,
+      directory: '/repo',
+      sessionId: 'ses_batch',
+      messageId: 'msg_batch',
+      signal: new AbortController().signal,
+    });
+
+    expect(result.size).toBe(12);
+    expect(requestCount).toBe(1);
+  });
+
+  test('reuses preparation for one thousand messages after virtualized remounts', async () => {
+    requestCount = 0;
+    const requests = Array.from({ length: 1000 }, (_, index) => ({
+      sources: [`${index}.png`],
+      directory: '/repo',
+      sessionId: 'ses_long',
+      messageId: `msg_${index}`,
+      signal: new AbortController().signal,
+    }));
+
+    for (const request of requests) await prepareLocalMarkdownImages(request);
+    for (const request of requests) await prepareLocalMarkdownImages(request);
+
+    expect(requestCount).toBe(1000);
+  });
+
+  test('reuses the existing authenticated raw-file asset URL', () => {
+    const url = getPreparedMarkdownImageUrl({
+      status: 'ready',
+      path: '/tmp/opencode/image.png',
+      outsideFileGrant: 'grant-1',
+    }, '/repo');
+
+    expect(url).toContain('/api/fs/raw?');
+    expect(url).toContain('path=%2Ftmp%2Fopencode%2Fimage.png');
+    expect(url).toContain('outsideFileGrant=grant-1');
+  });
+});
diff --git a/packages/ui/src/components/chat/markdown/markdownImageAssets.ts b/packages/ui/src/components/chat/markdown/markdownImageAssets.ts
index e61fea18..0cfc5fef 100644
--- a/packages/ui/src/components/chat/markdown/markdownImageAssets.ts
+++ b/packages/ui/src/components/chat/markdown/markdownImageAssets.ts
@@ -1,7 +1,9 @@
-import { isFilePathWithinDirectory, toAbsoluteFilePath } from '@/lib/path-utils';
 import { runtimeFetch } from '@/lib/runtime-fetch';
+import { getRuntimeUrlResolver, type RuntimeUrlResolver } from '@/lib/runtime-url';
 
 const MAX_MARKDOWN_IMAGE_BYTES = 10 * 1024 * 1024;
+const MAX_PREPARE_CACHE_ENTRIES = 1024;
+const NON_READY_CACHE_MS = 30_000;
 const SUPPORTED_IMAGE_MIME_TYPES = new Set([
   'image/png',
   'image/jpeg',
@@ -9,37 +11,20 @@ const SUPPORTED_IMAGE_MIME_TYPES = new Set([
   'image/webp',
 ]);
 
-const parseLocalImagePath = (source: string): string => {
-  let value = source;
-  if (/^file:\/\//i.test(value)) {
-    try {
-      const fileUrl = new URL(value);
-      if (fileUrl.protocol !== 'file:') return '';
-      value = fileUrl.host && fileUrl.host !== 'localhost'
-        ? `//${fileUrl.host}${fileUrl.pathname}`
-        : fileUrl.pathname;
-      if (/^\/[A-Za-z]:\//.test(value)) value = value.slice(1);
-    } catch {
-      return '';
-    }
-  }
+export type PreparedMarkdownImage =
+  | { status: 'ready'; path: string; outsideFileGrant?: string; expiresAt?: number }
+  | { status: 'missing' | 'error' };
 
-  const path = value.split(/[?#]/, 1)[0] ?? '';
-  try {
-    return decodeURIComponent(path);
-  } catch {
-    return path;
-  }
+type PrepareCacheEntry = {
+  result: Map<string, PreparedMarkdownImage>;
+  expiresAt: number;
 };
 
-const blobToDataUrl = (blob: Blob): Promise<string> => new Promise((resolve, reject) => {
-  const reader = new FileReader();
-  reader.onload = () => typeof reader.result === 'string'
-    ? resolve(reader.result)
-    : reject(new Error('Unable to encode image'));
-  reader.onerror = () => reject(reader.error ?? new Error('Unable to encode image'));
-  reader.readAsDataURL(blob);
-});
+const prepareCaches = new WeakMap<RuntimeUrlResolver, Map<string, PrepareCacheEntry>>();
+
+const throwIfAborted = (signal: AbortSignal): void => {
+  if (signal.aborted) throw new DOMException('Image load aborted', 'AbortError');
+};
 
 const hasImageSignature = async (blob: Blob, mimeType: string): Promise<boolean> => {
   const bytes = new Uint8Array(await blob.slice(0, 12).arrayBuffer());
@@ -48,9 +33,7 @@ const hasImageSignature = async (blob: Blob, mimeType: string): Promise<boolean>
     return bytes[0] === 0x89 && ascii(1, 4) === 'PNG'
       && bytes[4] === 0x0d && bytes[5] === 0x0a && bytes[6] === 0x1a && bytes[7] === 0x0a;
   }
-  if (mimeType === 'image/jpeg') {
-    return bytes[0] === 0xff && bytes[1] === 0xd8 && bytes[2] === 0xff;
-  }
+  if (mimeType === 'image/jpeg') return bytes[0] === 0xff && bytes[1] === 0xd8 && bytes[2] === 0xff;
   if (mimeType === 'image/gif') {
     const gif = ascii(0, 6);
     return gif === 'GIF87a' || gif === 'GIF89a';
@@ -67,66 +50,123 @@ const validateImageBlob = async (blob: Blob, mimeType: string): Promise<void> =>
 const validateDataImage = async (source: string): Promise<void> => {
   const match = /^data:(image\/(?:png|jpeg|gif|webp));base64,([\s\S]*)$/i.exec(source);
   if (!match?.[1] || match[2] === undefined) throw new Error('Invalid image data URL');
-  const encoded = match[2];
-  if (encoded.length > Math.ceil(MAX_MARKDOWN_IMAGE_BYTES * 4 / 3) + 4) {
-    throw new Error('Image is too large');
-  }
-
+  if (match[2].length > Math.ceil(MAX_MARKDOWN_IMAGE_BYTES * 4 / 3) + 4) throw new Error('Image is too large');
   let binary: string;
   try {
-    binary = atob(encoded);
+    binary = atob(match[2]);
   } catch {
     throw new Error('Invalid image data URL');
   }
-  const bytes = new Uint8Array(binary.length);
-  for (let index = 0; index < binary.length; index += 1) bytes[index] = binary.charCodeAt(index);
+  const bytes = Uint8Array.from(binary, (character) => character.charCodeAt(0));
   await validateImageBlob(new Blob([bytes]), match[1].toLowerCase());
 };
 
+export const isLocalMarkdownImageSource = (source: string): boolean => (
+  !/^(?:https?:)?\/\//i.test(source)
+  && !/^data:image\/(?:png|jpeg|gif|webp);base64,/i.test(source)
+);
+
+export const prepareLocalMarkdownImages = async ({
+  sources,
+  directory,
+  sessionId,
+  messageId,
+  signal,
+}: {
+  sources: readonly string[];
+  directory: string;
+  sessionId: string;
+  messageId: string;
+  signal: AbortSignal;
+}): Promise<Map<string, PreparedMarkdownImage>> => {
+  const resolver = getRuntimeUrlResolver();
+  let cache = prepareCaches.get(resolver);
+  if (!cache) {
+    cache = new Map();
+    prepareCaches.set(resolver, cache);
+  }
+  const key = `${sessionId}\0${messageId}\0${directory}\0${sources.join('\0')}`;
+  const cached = cache.get(key);
+  if (cached && cached.expiresAt > Date.now()) {
+    cache.delete(key);
+    cache.set(key, cached);
+    return cached.result;
+  }
+  if (cached) cache.delete(key);
+
+  const response = await runtimeFetch(
+    `/api/openchamber/sessions/${encodeURIComponent(sessionId)}/markdown-image-grants`,
+    {
+      method: 'POST',
+      headers: { 'content-type': 'application/json' },
+      body: JSON.stringify({ directory, messageId, sources }),
+      signal,
+    },
+  );
+  if (!response.ok) throw new Error(`Unable to prepare images (${response.status})`);
+  const payload = await response.json() as {
+    results?: Array<{
+      source?: string;
+      status?: string;
+      path?: string;
+      outsideFileGrant?: string;
+      expiresAt?: number;
+    }>;
+  };
+  const prepared = new Map<string, PreparedMarkdownImage>();
+  for (const result of payload.results ?? []) {
+    if (!result.source) continue;
+    if (result.status === 'ready' && result.path) {
+      prepared.set(result.source, {
+        status: 'ready',
+        path: result.path,
+        outsideFileGrant: result.outsideFileGrant,
+        expiresAt: result.expiresAt,
+      });
+    } else if (result.status === 'missing') {
+      prepared.set(result.source, { status: 'missing' });
+    } else {
+      prepared.set(result.source, { status: 'error' });
+    }
+  }
+  for (const source of sources) {
+    if (!prepared.has(source)) prepared.set(source, { status: 'error' });
+  }
+  while (cache.size >= MAX_PREPARE_CACHE_ENTRIES) cache.delete(cache.keys().next().value!);
+  const allReady = [...prepared.values()].every((value) => value.status === 'ready');
+  const grantExpiry = Math.min(...[...prepared.values()]
+    .filter((value): value is Extract<PreparedMarkdownImage, { status: 'ready' }> => value.status === 'ready')
+    .map((value) => value.expiresAt ?? Number.POSITIVE_INFINITY));
+  cache.set(key, {
+    result: prepared,
+    expiresAt: allReady ? grantExpiry : Date.now() + NON_READY_CACHE_MS,
+  });
+  return prepared;
+};
+
 export const resolveMarkdownImageSource = async (
   source: string,
-  directory: string,
   signal: AbortSignal,
 ): Promise<string> => {
-  if (signal.aborted) throw new DOMException('Image load aborted', 'AbortError');
+  throwIfAborted(signal);
   if (/^(?:https?:)?\/\//i.test(source)) return source;
-
   if (/^data:image\/(?:png|jpeg|gif|webp);base64,/i.test(source)) {
     await validateDataImage(source);
-    if (signal.aborted) throw new DOMException('Image load aborted', 'AbortError');
+    throwIfAborted(signal);
     return source;
   }
-
-  const localPath = parseLocalImagePath(source);
-  const absolutePath = toAbsoluteFilePath(directory, localPath);
-  if (!directory || !localPath || !isFilePathWithinDirectory(absolutePath, directory)) {
-    throw new Error('Image path is outside the active workspace');
-  }
-
-  const statResponse = await runtimeFetch('/api/fs/stat', {
-    query: { path: absolutePath, directory, optional: 'true' },
-    signal,
-  });
-  if (!statResponse.ok) throw new Error(`Unable to inspect image (${statResponse.status})`);
-  const stat = await statResponse.json() as { isFile?: boolean; size?: number };
-  if (!stat.isFile) throw new Error('Image path is not a file');
-  if (typeof stat.size === 'number' && stat.size > MAX_MARKDOWN_IMAGE_BYTES) {
-    throw new Error('Image is too large');
-  }
-
-  const response = await runtimeFetch('/api/fs/raw', {
-    query: { path: absolutePath, directory },
-    signal,
-  });
-  if (!response.ok) throw new Error(`Unable to load image (${response.status})`);
-
-  const mimeType = (response.headers.get('content-type') ?? '').split(';', 1)[0]?.toLowerCase() ?? '';
-  const contentLength = Number(response.headers.get('content-length'));
-  if (Number.isFinite(contentLength) && contentLength > MAX_MARKDOWN_IMAGE_BYTES) {
-    throw new Error('Image is too large');
-  }
-
-  const blob = await response.blob();
-  await validateImageBlob(blob, mimeType);
-  return blobToDataUrl(blob);
+  throw new Error('Local image has not been prepared');
 };
+
+export const getPreparedMarkdownImageUrl = (
+  image: Extract<PreparedMarkdownImage, { status: 'ready' }>,
+  directory: string,
+): string => getRuntimeUrlResolver().authenticatedAsset(
+  '/api/fs/raw',
+  {
+    path: image.path,
+    directory,
+    allowOutsideWorkspace: image.outsideFileGrant ? 'true' : undefined,
+    outsideFileGrant: image.outsideFileGrant,
+  },
+  );
diff --git a/packages/ui/src/components/chat/message/MessageBody.tsx b/packages/ui/src/components/chat/message/MessageBody.tsx
index 7199edfc..44e53291 100644
--- a/packages/ui/src/components/chat/message/MessageBody.tsx
+++ b/packages/ui/src/components/chat/message/MessageBody.tsx
@@ -1876,7 +1876,6 @@ const AssistantMessageBody = React.memo(({
                             chatRenderMode={chatRenderMode}
                             onContentChange={onContentChange}
                             onShowPopup={onShowPopup}
-                            enableMarkdownImages={isMessageCompleted}
                         />
                     </div>
                 );
@@ -2031,7 +2030,6 @@ const AssistantMessageBody = React.memo(({
         collapsedPreviewCount,
         expandedTools,
         isMobile,
-        isMessageCompleted,
         isActivityOwnerMessage,
         isSortedRenderMode,
         lastRenderableTextPartIndex,
@@ -2244,6 +2242,8 @@ const AssistantMessageBody = React.memo(({
                 </div>
                 <MessageFilesDisplay files={parts} onShowPopup={onShowPopup} />
                 <MarkdownImageGallery
+                    sessionId={sessionId}
+                    messageId={messageId}
                     contents={finalizedAssistantMarkdownContents}
                     onShowPopup={onShowPopup}
                 />
diff --git a/packages/ui/src/components/chat/message/parts/AssistantTextPart.tsx b/packages/ui/src/components/chat/message/parts/AssistantTextPart.tsx
index cfcbbaa7..74b34b24 100644
--- a/packages/ui/src/components/chat/message/parts/AssistantTextPart.tsx
+++ b/packages/ui/src/components/chat/message/parts/AssistantTextPart.tsx
@@ -19,7 +19,6 @@ interface AssistantTextPartProps {
     chatRenderMode?: 'sorted' | 'live';
     onContentChange?: (reason?: ContentChangeReason, messageId?: string) => void;
     onShowPopup?: (content: ToolPopupContent) => void;
-    enableMarkdownImages?: boolean;
 }
 
 const AssistantTextPart: React.FC<AssistantTextPartProps> = ({
@@ -28,7 +27,6 @@ const AssistantTextPart: React.FC<AssistantTextPartProps> = ({
     streamPhase,
     chatRenderMode = 'live',
     onShowPopup,
-    enableMarkdownImages = false,
 }) => {
     // Use part directly from props — parent provides the latest version from the store.
     // No store subscription here to avoid re-render cascade from unrelated delta events.
@@ -103,7 +101,6 @@ const AssistantTextPart: React.FC<AssistantTextPartProps> = ({
                 disableStreamAnimation={chatRenderMode === 'sorted'}
                 variant={part.type === 'reasoning' ? 'reasoning' : 'assistant'}
                 enableFileReferences={isFinalized}
-                enableLocalImages={enableMarkdownImages && !isStreaming && part.type === 'text'}
                 onShowPopup={onShowPopup}
             />
         </div>
diff --git a/packages/ui/src/components/chat/message/parts/DOCUMENTATION.md b/packages/ui/src/components/chat/message/parts/DOCUMENTATION.md
index fb23b92a..3034a28f 100644
--- a/packages/ui/src/components/chat/message/parts/DOCUMENTATION.md
+++ b/packages/ui/src/components/chat/message/parts/DOCUMENTATION.md
@@ -55,23 +55,30 @@ Use this doc when you ask an agent to change tool/header/description behavior.
   HTML is sanitized as defense in depth, with script and style elements
   forbidden, so message content cannot inject active DOM or application-wide
   CSS into any runtime surface.
-- Final assistant Markdown collects HTTP(S), embedded, and workspace-local
+- Final assistant Markdown rendering is independent from image gallery
+  extraction: gallery presence never changes the chat body. Assistant image
+  syntax consistently renders as a shared image icon followed by its filename,
+  without loading the image in the body; tool and simple Markdown retain normal
+  inline image rendering. The gallery separately collects HTTP(S), embedded, and workspace-local
   PNG/JPEG/GIF/WebP image candidates into one 100px thumbnail gallery in the
   message-completion area after all message text and above the turn's changed
   files. Each muted filename caption includes the shared image-file icon.
-  HTTP(S) images keep their browser URL. Embedded and workspace-local images
-  are limited to 10 MiB, validated as PNG/JPEG/GIF/WebP, and local paths are
-  fetched through the active runtime before conversion to data URLs. Local
-  Markdown links whose target has one of
-  those image suffixes stay links in the text and open the same existing
-  full-screen image preview as the gallery; image syntax does not insert a
-  large inline image. A
+  HTTP(S) images keep their browser URL. Embedded and workspace-local gallery
+  images are limited to 10 MiB and validated as PNG/JPEG/GIF/WebP. Local paths
+  reuse the existing authenticated `/api/fs/raw` asset URL. Chat
+  Markdown uses the assistant image-label policy without gallery-specific
+  link rewriting, completion-state switching, or hidden placeholders. A
   completed assistant message hydrates at most 12 unique image candidates,
   including persisted text parts that omit their optional part-level end time.
-  Thumbnail assets begin loading only when their gallery items approach the
-  viewport, so mounted historical messages do not eagerly read every image.
+  A gallery approaching the viewport prepares all local candidates in one
+  message-level request, while each asset URL loads only when its own thumbnail
+  approaches the viewport. Mounted historical messages therefore do not
+  eagerly read every image.
   Gallery clicks do not introduce or alter preview chrome: desktop and mobile
   both reuse the pre-existing attachment image preview overlay.
+  Workspace-external images receive the existing path-bound `outsideFileGrant`
+  only when the server verifies the exact source in the owning assistant
+  message and the real file is inside OpenCode's dedicated temporary directory.
 - `read` and `skill` are **static navigation tools** and render via `StaticToolRow`.
 - Every other tool, including search/fetch, OpenCode built-ins, custom tools, plugins, and MCP tools, is **expandable** and renders through `ToolPart`.
 - The managed `openchamber` plugin tool uses the expandable path and hides its broad protocol input. The plugin supplies the selected action's human description as the native tool title; the UI renders that metadata without owning an action map. The full versioned result envelope renders through the same neutral JSON summary/tree/raw views as other tools, without a tool-specific output card.
diff --git a/packages/ui/src/index.css b/packages/ui/src/index.css
index 585cddba..b5969d69 100644
--- a/packages/ui/src/index.css
+++ b/packages/ui/src/index.css
@@ -1151,12 +1151,6 @@ html:not(.dark) .chat-scroll {
   color: var(--markdown-link-hover, var(--primary));
 }
 
-[data-openchamber-finalized-assistant-images="true"] [data-openchamber-markdown-image-placeholder="true"],
-[data-openchamber-finalized-assistant-images="true"] p:has(> [data-openchamber-markdown-image-placeholder="true"]:only-child),
-[data-openchamber-finalized-assistant-images="true"] li:has(> [data-openchamber-markdown-image-placeholder="true"]:only-child) {
-  display: none;
-}
-
 .markdown-content [data-openchamber-file-link="true"] {
   color: var(--markdown-link, var(--primary));
   cursor: pointer;
diff --git a/packages/vscode/src/DOCUMENTATION.md b/packages/vscode/src/DOCUMENTATION.md
index 69fd0a4a..2b80c63b 100644
--- a/packages/vscode/src/DOCUMENTATION.md
+++ b/packages/vscode/src/DOCUMENTATION.md
@@ -45,6 +45,7 @@ The webview CSP permits `blob:` only for `worker-src` so shared UI parsers can r
 
 - `bridge-localfs-proxy-runtime.ts`
   - Local `/api/fs/read` and `/api/fs/raw` proxy helpers and shared proxy utility helpers.
+  - Returns an explicit unsupported response for server-owned Markdown image grants instead of forwarding them to OpenCode.
 
 - `bridge-proxy-runtime.ts`
   - Proxy route handlers (`api:proxy`, `api:session:message`) with injected helper dependencies.
diff --git a/packages/vscode/src/bridge-localfs-proxy-runtime.test.js b/packages/vscode/src/bridge-localfs-proxy-runtime.test.js
index 02cdf654..617eac7a 100644
--- a/packages/vscode/src/bridge-localfs-proxy-runtime.test.js
+++ b/packages/vscode/src/bridge-localfs-proxy-runtime.test.js
@@ -37,6 +37,14 @@ mock.module('vscode', () => ({
 const { tryHandleLocalFsProxy } = await import('./bridge-localfs-proxy-runtime');
 
 describe('bridge local fs proxy', () => {
+  it('does not forward server-owned Markdown image grant routes to OpenCode', async () => {
+    const response = await tryHandleLocalFsProxy('POST', '/api/openchamber/sessions/ses_1/markdown-image-grants');
+
+    expect(response?.status).toBe(501);
+    expect(Buffer.from(response?.bodyBase64 ?? '', 'base64').toString('utf8'))
+      .toContain('not supported in the VS Code runtime');
+  });
+
   it('returns a quiet optional stat miss for missing files', async () => {
     const response = await tryHandleLocalFsProxy('GET', '/api/fs/stat?path=%2Fmissing.ts&optional=true');
 
diff --git a/packages/vscode/src/bridge-localfs-proxy-runtime.ts b/packages/vscode/src/bridge-localfs-proxy-runtime.ts
index d0439071..ba1f3093 100644
--- a/packages/vscode/src/bridge-localfs-proxy-runtime.ts
+++ b/packages/vscode/src/bridge-localfs-proxy-runtime.ts
@@ -56,6 +56,9 @@ export const tryHandleLocalFsProxy = async (method: string, requestPath: string)
   }
 
   const fsProxyPath = normalizeFsProxyPath(parsed.pathname);
+  if (/^\/api\/openchamber\/sessions\/[^/]+\/markdown-image-grants$/.test(parsed.pathname)) {
+    return buildProxyJsonError(501, 'Markdown image grants are not supported in the VS Code runtime');
+  }
   if (!fsProxyPath) {
     return null;
   }
diff --git a/packages/web/server/lib/markdown-image-grants/DOCUMENTATION.md b/packages/web/server/lib/markdown-image-grants/DOCUMENTATION.md
new file mode 100644
index 00000000..f92603fe
--- /dev/null
+++ b/packages/web/server/lib/markdown-image-grants/DOCUMENTATION.md
@@ -0,0 +1,30 @@
+# Markdown Image Grants
+
+## Purpose
+
+This module lets the Markdown image gallery display images that an assistant
+explicitly referenced from OpenCode's temporary directory when the UI is on a
+different machine.
+
+## Contract
+
+- Chat Markdown rendering is independent: assistant image syntax renders as an
+  icon and filename, while the gallery only reads finalized Markdown to collect
+  image candidates.
+- `POST /api/openchamber/sessions/:sessionId/markdown-image-grants` prepares up to 12
+  local images in one message-level request. The server fetches the assistant
+  message once and verifies every exact image source before reading files.
+- Relative and workspace-contained absolute paths resolve against the active
+  directory. Other absolute paths are accepted only inside
+  `os.tmpdir()/opencode` after `realpath` resolution.
+- PNG, JPEG, GIF, and WebP files are signature-checked and limited to 10 MiB.
+- Prepare requests inspect only file metadata and signatures. Workspace images
+  reuse the existing authenticated `/api/fs/raw` asset route directly. Images
+  under `os.tmpdir()/opencode` receive the existing path-bound `raw`
+  `outsideFileGrant`; this module does not add another asset lifetime, copy, or
+  storage layer. Missing files return per-source results so the gallery can
+  remove only those items.
+
+The routes are OpenChamber-owned and must be registered before the generic
+OpenCode proxy. Web, Electron, hosted mobile, and Capacitor use the shared
+server implementation. VS Code returns an explicit unsupported response.
diff --git a/packages/web/server/lib/markdown-image-grants/routes.js b/packages/web/server/lib/markdown-image-grants/routes.js
new file mode 100644
index 00000000..8225666a
--- /dev/null
+++ b/packages/web/server/lib/markdown-image-grants/routes.js
@@ -0,0 +1,215 @@
+import express from 'express';
+import { constants as fsConstants } from 'node:fs';
+import { mintOutsideFileGrant } from '../fs/routes.js';
+
+const MAX_IMAGE_BYTES = 10 * 1024 * 1024;
+const MAX_IMAGE_SOURCES = 12;
+
+const asString = (value) => typeof value === 'string' ? value.trim() : '';
+
+const isWithin = (target, root, path) => {
+  const relative = path.relative(root, target);
+  return relative === '' || (!relative.startsWith('..') && !path.isAbsolute(relative));
+};
+
+const parseFileSource = (source) => {
+  if (/^file:\/\//i.test(source)) {
+    try {
+      const url = new URL(source);
+      if (url.protocol !== 'file:' || (url.host && url.host !== 'localhost')) return '';
+      const pathname = decodeURIComponent(url.pathname);
+      return /^\/[A-Za-z]:\//.test(pathname) ? pathname.slice(1) : pathname;
+    } catch {
+      return '';
+    }
+  }
+  const pathname = source.split(/[?#]/, 1)[0] || '';
+  try {
+    return decodeURIComponent(pathname);
+  } catch {
+    return pathname;
+  }
+};
+
+const hasImageSignature = (bytes) => {
+  if (bytes.length >= 8
+    && bytes[0] === 0x89 && bytes.subarray(1, 4).toString('ascii') === 'PNG'
+    && bytes[4] === 0x0d && bytes[5] === 0x0a && bytes[6] === 0x1a && bytes[7] === 0x0a) return true;
+  if (bytes.length >= 3 && bytes[0] === 0xff && bytes[1] === 0xd8 && bytes[2] === 0xff) return true;
+  const header = bytes.subarray(0, 12).toString('ascii');
+  return header.startsWith('GIF87a')
+    || header.startsWith('GIF89a')
+    || (header.startsWith('RIFF') && header.slice(8, 12) === 'WEBP');
+};
+
+const markdownImageSources = (message) => {
+  const sources = new Set();
+  for (const part of Array.isArray(message?.parts) ? message.parts : []) {
+    if (part?.type !== 'text' || typeof part.text !== 'string') continue;
+    // Code examples must never authorize file access, even when they contain image syntax.
+    let fenced = false;
+    for (const line of part.text.split('\n')) {
+      if (/^\s{0,3}(?:```|~~~)/.test(line)) {
+        fenced = !fenced;
+        continue;
+      }
+      if (fenced) continue;
+      const visible = line.replace(/`+[^`]*`+/g, '');
+      const pattern = /(?<!\\)!\[[^\]]*]\(\s*(?:<([^>\n]+)>|([^\s)\n]+))/g;
+      let match = pattern.exec(visible);
+      while (match) {
+        sources.add(match[1] || match[2]);
+        match = pattern.exec(visible);
+      }
+    }
+  }
+  return sources;
+};
+
+const fetchMessage = async ({ sessionId, messageId, directory, buildOpenCodeUrl, getOpenCodeAuthHeaders }) => {
+  const url = new URL(buildOpenCodeUrl(
+    `/session/${encodeURIComponent(sessionId)}/message/${encodeURIComponent(messageId)}`,
+    '',
+  ));
+  url.searchParams.set('directory', directory);
+  const response = await fetch(url, {
+    headers: {
+      accept: 'application/json',
+      'x-opencode-directory': directory,
+      ...getOpenCodeAuthHeaders(),
+    },
+    signal: AbortSignal.timeout(10_000),
+  });
+  if (response.status === 404) return null;
+  if (!response.ok) throw new Error(`OpenCode returned ${response.status}`);
+  const message = await response.json().catch(() => null);
+  return message?.info && Array.isArray(message.parts) ? message : null;
+};
+
+const inspectImage = async ({ source, directory, approvedTempRoot, fsPromises, path }) => {
+  const parsed = parseFileSource(source);
+  if (!parsed) return { status: 'error' };
+  const sourcePath = path.isAbsolute(parsed) ? parsed : path.resolve(directory, parsed);
+  const workspaceRoot = path.resolve(directory);
+  const outsideWorkspace = !isWithin(path.resolve(sourcePath), workspaceRoot, path);
+  const root = outsideWorkspace ? approvedTempRoot : workspaceRoot;
+
+  try {
+    // Resolve symlinks before comparing roots; lexical prefixes are not an authorization boundary.
+    const [canonicalRoot, canonicalPath] = await Promise.all([
+      fsPromises.realpath(root),
+      fsPromises.realpath(sourcePath),
+    ]);
+    if (!isWithin(canonicalPath, canonicalRoot, path)) return { status: 'error' };
+    const handle = await fsPromises.open(canonicalPath, fsConstants.O_RDONLY | fsConstants.O_NOFOLLOW);
+    try {
+      const stats = await handle.stat();
+      if (!stats.isFile() || stats.size > MAX_IMAGE_BYTES) return { status: 'error' };
+      const header = Buffer.alloc(12);
+      const { bytesRead } = await handle.read(header, 0, header.length, 0);
+      if (!hasImageSignature(header.subarray(0, bytesRead))) return { status: 'error' };
+      return {
+        status: 'ready',
+        path: outsideWorkspace ? canonicalPath : path.resolve(sourcePath),
+        outsideWorkspace,
+      };
+    } finally {
+      await handle.close();
+    }
+  } catch (error) {
+    if (error?.code === 'ENOENT') return { status: 'missing' };
+    if (error?.code === 'EACCES' || error?.code === 'EPERM' || error?.code === 'ELOOP') {
+      return { status: 'error' };
+    }
+    throw error;
+  }
+};
+
+export const registerMarkdownImageGrantRoutes = (app, dependencies) => {
+  const {
+    fsPromises,
+    path,
+    os,
+    crypto,
+    validateDirectoryPath,
+    buildOpenCodeUrl,
+    getOpenCodeAuthHeaders,
+    approvedTempRoot = path.join(os.tmpdir(), 'opencode'),
+  } = dependencies;
+
+  app.post(
+    '/api/openchamber/sessions/:sessionId/markdown-image-grants',
+    express.json({ limit: '32kb' }),
+    async (req, res) => {
+      const sessionId = asString(req.params.sessionId);
+      const messageId = asString(req.body?.messageId);
+      const sources = Array.isArray(req.body?.sources)
+        ? [...new Set(req.body.sources.map(asString).filter(Boolean))]
+        : [];
+      if (!sessionId || !messageId || sources.length === 0 || sources.length > MAX_IMAGE_SOURCES) {
+        return res.status(400).json({ error: 'sessionId, messageId, and 1-12 sources are required' });
+      }
+      const validatedDirectory = await validateDirectoryPath(asString(req.body?.directory));
+      if (!validatedDirectory.ok) {
+        return res.status(400).json({ error: validatedDirectory.error || 'Invalid directory' });
+      }
+
+      try {
+        const message = await fetchMessage({
+          sessionId,
+          messageId,
+          directory: validatedDirectory.directory,
+          buildOpenCodeUrl,
+          getOpenCodeAuthHeaders,
+        });
+        if (!message || message.info?.id !== messageId || message.info?.role !== 'assistant') {
+          return res.status(404).json({ error: 'Assistant message not found' });
+        }
+        // Assistant text is authoritative: a remote client cannot mint grants for unreferenced paths.
+        const referenced = markdownImageSources(message);
+        const results = [];
+        for (const source of sources) {
+          if (!referenced.has(source)) {
+            results.push({ source, status: 'error' });
+            continue;
+          }
+          try {
+            const inspected = await inspectImage({
+              source,
+              directory: validatedDirectory.directory,
+              approvedTempRoot,
+              fsPromises,
+              path,
+            });
+            if (inspected.status !== 'ready') {
+              results.push({ source, status: inspected.status });
+              continue;
+            }
+            // Reuse the existing path-bound raw-file grant instead of creating another asset lifecycle.
+            const grant = inspected.outsideWorkspace
+              ? await mintOutsideFileGrant(inspected.path, {
+                scopes: ['raw'],
+                fsPromises,
+                path,
+                crypto,
+              })
+              : null;
+            results.push({
+              source,
+              status: 'ready',
+              path: inspected.path,
+              outsideFileGrant: grant?.outsideFileGrant,
+              expiresAt: grant?.expiresAt,
+            });
+          } catch {
+            results.push({ source, status: 'error' });
+          }
+        }
+        return res.json({ results });
+      } catch (error) {
+        console.warn('[MarkdownImageGrants] failed to prepare images:', error?.message || error);
+        return res.status(503).json({ error: 'Failed to prepare session images' });
+      }
+    },
+  );
+};
diff --git a/packages/web/server/lib/markdown-image-grants/routes.test.js b/packages/web/server/lib/markdown-image-grants/routes.test.js
new file mode 100644
index 00000000..3a08c691
--- /dev/null
+++ b/packages/web/server/lib/markdown-image-grants/routes.test.js
@@ -0,0 +1,175 @@
+import { afterEach, describe, expect, it, vi } from 'vitest';
+import express from 'express';
+import request from 'supertest';
+import crypto from 'node:crypto';
+import fs from 'node:fs/promises';
+import os from 'node:os';
+import path from 'node:path';
+import { registerMarkdownImageGrantRoutes } from './routes.js';
+
+const PNG = Buffer.from(
+  'iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUlEQVR42mP8z8DwHwAFBQIAX8jx0gAAAABJRU5ErkJggg==',
+  'base64',
+);
+const roots = [];
+
+afterEach(async () => {
+  vi.unstubAllGlobals();
+  await Promise.all(roots.splice(0).map((root) => fs.rm(root, { recursive: true, force: true })));
+});
+
+const createFixture = async ({ sources, markdown } = {}) => {
+  const root = await fs.mkdtemp(path.join(os.tmpdir(), 'openchamber-session-assets-'));
+  roots.push(root);
+  const approvedTempRoot = path.join(root, 'opencode');
+  const directory = path.join(root, 'workspace');
+  await Promise.all([
+    fs.mkdir(approvedTempRoot, { recursive: true }),
+    fs.mkdir(directory, { recursive: true }),
+  ]);
+  const defaultPath = path.join(approvedTempRoot, 'image.png');
+  await fs.writeFile(defaultPath, PNG);
+  const requestedSources = sources ?? [new URL(`file://${defaultPath}`).toString()];
+  const text = markdown ?? requestedSources.map((source) => `![image](${source})`).join('\n');
+  const fetchMock = vi.fn(async () => new Response(JSON.stringify({
+    info: { id: 'msg_1', role: 'assistant' },
+    parts: [{ type: 'text', text }],
+  }), { status: 200, headers: { 'content-type': 'application/json' } }));
+  vi.stubGlobal('fetch', fetchMock);
+
+  let fullReadCount = 0;
+  const app = express();
+  registerMarkdownImageGrantRoutes(app, {
+    fsPromises: {
+      ...fs,
+      readFile: async (...args) => {
+        fullReadCount += 1;
+        return fs.readFile(...args);
+      },
+    },
+    path,
+    os,
+    crypto,
+    approvedTempRoot,
+    validateDirectoryPath: async (candidate) => candidate === directory
+      ? { ok: true, directory }
+      : { ok: false, error: 'Invalid directory' },
+    buildOpenCodeUrl: (route) => `http://opencode.test${route}`,
+    getOpenCodeAuthHeaders: () => ({ authorization: 'Basic test' }),
+  });
+  return {
+    app,
+    approvedTempRoot,
+    directory,
+    fetchMock,
+    fullReadCount: () => fullReadCount,
+    root,
+    sources: requestedSources,
+  };
+};
+
+const prepare = (app, directory, sources) => request(app)
+  .post('/api/openchamber/sessions/ses_1/markdown-image-grants')
+  .send({ directory, messageId: 'msg_1', sources })
+  .expect(200);
+
+describe('session image assets', () => {
+  it('prepares workspace and OpenCode temporary images with one message fetch', async () => {
+    const fixture = await createFixture({ sources: ['workspace.png'] });
+    await fs.writeFile(path.join(fixture.directory, 'workspace.png'), PNG);
+    const temporaryPath = path.join(fixture.approvedTempRoot, 'temporary.png');
+    await fs.writeFile(temporaryPath, PNG);
+    const temporarySource = new URL(`file://${temporaryPath}`).toString();
+    fixture.fetchMock.mockResolvedValueOnce(new Response(JSON.stringify({
+      info: { id: 'msg_1', role: 'assistant' },
+      parts: [{ type: 'text', text: `![workspace](workspace.png)\n![temporary](${temporarySource})` }],
+    }), { status: 200, headers: { 'content-type': 'application/json' } }));
+
+    const response = await prepare(fixture.app, fixture.directory, ['workspace.png', temporarySource]);
+
+    expect(fixture.fetchMock).toHaveBeenCalledTimes(1);
+    expect(fixture.fullReadCount()).toBe(0);
+    expect(response.body.results).toHaveLength(2);
+    const canonicalTemporaryPath = await fs.realpath(temporaryPath);
+    expect(response.body.results[0]).toEqual({
+      source: 'workspace.png',
+      status: 'ready',
+      path: path.join(fixture.directory, 'workspace.png'),
+    });
+    expect(response.body.results[1]).toEqual(expect.objectContaining({
+      source: temporarySource,
+      status: 'ready',
+      path: canonicalTemporaryPath,
+      outsideFileGrant: expect.any(String),
+      expiresAt: expect.any(Number),
+    }));
+  });
+
+  it('returns partial results without letting one missing image block valid images', async () => {
+    const fixture = await createFixture({ sources: ['present.png', 'deleted.png'] });
+    await fs.writeFile(path.join(fixture.directory, 'present.png'), PNG);
+
+    const response = await prepare(fixture.app, fixture.directory, fixture.sources);
+
+    expect(response.body.results).toEqual([
+      expect.objectContaining({ source: 'present.png', status: 'ready' }),
+      { source: 'deleted.png', status: 'missing' },
+    ]);
+  });
+
+  it('resolves encoded workspace paths without treating query or fragment text as a filename', async () => {
+    const source = 'screen%20shot.png?version=1#preview';
+    const fixture = await createFixture({ sources: [source] });
+    await fs.writeFile(path.join(fixture.directory, 'screen shot.png'), PNG);
+
+    const response = await prepare(fixture.app, fixture.directory, fixture.sources);
+
+    expect(response.body.results).toEqual([
+      expect.objectContaining({ source, status: 'ready' }),
+    ]);
+  });
+
+  it('rejects a source that the message does not reference', async () => {
+    const fixture = await createFixture({ markdown: 'No image here.' });
+    const response = await prepare(fixture.app, fixture.directory, fixture.sources);
+    expect(response.body.results).toEqual([{ source: fixture.sources[0], status: 'error' }]);
+  });
+
+  it('does not authorize image syntax inside fenced or inline code', async () => {
+    const fixture = await createFixture({
+      markdown: '```md\n![fenced](FENCED)\n```\n`![inline](INLINE)`',
+    });
+    const sources = ['FENCED', 'INLINE'];
+
+    const response = await prepare(fixture.app, fixture.directory, sources);
+
+    expect(response.body.results).toEqual(sources.map((source) => ({ source, status: 'error' })));
+  });
+
+  it('rejects paths outside the workspace and approved temporary root', async () => {
+    const fixture = await createFixture();
+    const outsidePath = path.join(fixture.root, 'outside.png');
+    await fs.writeFile(outsidePath, PNG);
+    const source = new URL(`file://${outsidePath}`).toString();
+    fixture.fetchMock.mockResolvedValueOnce(new Response(JSON.stringify({
+      info: { id: 'msg_1', role: 'assistant' },
+      parts: [{ type: 'text', text: `![outside](${source})` }],
+    }), { status: 200, headers: { 'content-type': 'application/json' } }));
+
+    const response = await prepare(fixture.app, fixture.directory, [source]);
+    expect(response.body.results).toEqual([{ source, status: 'error' }]);
+  });
+
+  it('rejects non-image bytes and symlink escapes per source', async () => {
+    const fixture = await createFixture({ sources: ['invalid.png', 'linked.png'] });
+    await fs.writeFile(path.join(fixture.directory, 'invalid.png'), 'not an image');
+    await fs.writeFile(path.join(fixture.root, 'outside.png'), PNG);
+    await fs.symlink(path.join(fixture.root, 'outside.png'), path.join(fixture.directory, 'linked.png'));
+
+    const response = await prepare(fixture.app, fixture.directory, fixture.sources);
+    expect(response.body.results).toEqual([
+      { source: 'invalid.png', status: 'error' },
+      { source: 'linked.png', status: 'error' },
+    ]);
+  });
+});
diff --git a/packages/web/server/lib/opencode/feature-routes-runtime.js b/packages/web/server/lib/opencode/feature-routes-runtime.js
index cfa66d2f..90c15f1b 100644
--- a/packages/web/server/lib/opencode/feature-routes-runtime.js
+++ b/packages/web/server/lib/opencode/feature-routes-runtime.js
@@ -15,6 +15,7 @@ import { registerProjectIconRoutes } from './project-icon-routes.js';
 import { registerScheduledTaskRoutes } from '../scheduled-tasks/routes.js';
 import { registerOpenChamberSessionRoutes } from '../openchamber-sessions/routes.js';
 import { registerOpenChamberControlRoutes } from '../openchamber-control/routes.js';
+import { registerMarkdownImageGrantRoutes } from '../markdown-image-grants/routes.js';
 import { registerSkillRoutes } from './skill-routes.js';
 import { registerPluginRoutes } from './plugin-routes.js';
 import { getNpmInfo, clearCache as clearNpmCache } from './npm-registry.js';
@@ -190,6 +191,16 @@ export const createFeatureRoutesRuntime = (dependencies) => {
 
     registerOpenChamberControlRoutes(app, { controlService: openChamberControlService });
 
+    registerMarkdownImageGrantRoutes(app, {
+      fsPromises,
+      path,
+      os,
+      crypto,
+      validateDirectoryPath,
+      buildOpenCodeUrl,
+      getOpenCodeAuthHeaders,
+    });
+
     registerConfigEntityRoutes(app, {
       resolveProjectDirectory,
       resolveOptionalProjectDirectory,