diff --git a/ui/src/components/markdown-assistant-transcript.ts b/ui/src/components/markdown-assistant-transcript.ts
index 31f8fba40fde..a0954b0f89f4 100644
--- a/ui/src/components/markdown-assistant-transcript.ts
+++ b/ui/src/components/markdown-assistant-transcript.ts
@@ -84,6 +84,11 @@ export function installAssistantTranscriptRoleImageRenderer(
     normalizeLabel: (value: string) => string;
     assistantLabel: () => string;
     openImageLabel: (alt: string, hasAlt: boolean) => string;
+    renderExternalImageFallback: (
+      src: string,
+      renderedLabel: string,
+      linkedImage: boolean,
+    ) => string;
     interactiveImages: (env: unknown) => boolean;
     allowRemoteImages: (env: unknown) => boolean;
   },
@@ -98,13 +103,14 @@ export function installAssistantTranscriptRoleImageRenderer(
     const alt = options.normalizeLabel(token.content);
     const roleMeta = (token.meta as AssistantTranscriptRoleImageMeta | undefined)
       ?.assistantTranscriptRoleImage;
+    const linkedImage = isImageWithinLink(tokens, index);
     if (!options.isInlineDataImage(src) && !options.allowRemoteImages(env)) {
-      return roleMeta
+      const renderedLabel = roleMeta
         ? renderAssistantTranscriptRoleImageLabel(roleMeta.text, roleMeta.spans, options.escapeHtml)
         : options.escapeHtml(alt);
+      return options.renderExternalImageFallback(src, renderedLabel, linkedImage);
     }
     const image = `<img class="markdown-inline-image" src="${options.escapeHtml(src)}" alt="${options.escapeHtml(alt)}">`;
-    const linkedImage = isImageWithinLink(tokens, index);
     const interactiveImage =
       linkedImage || !options.interactiveImages(env)
         ? image
diff --git a/ui/src/components/markdown-parser.ts b/ui/src/components/markdown-parser.ts
index 5d071d1b3dc6..3eab3b2929e7 100644
--- a/ui/src/components/markdown-parser.ts
+++ b/ui/src/components/markdown-parser.ts
@@ -571,8 +571,8 @@ export function createMarkdownParser(): MarkdownIt {
     return `<a class="markdown-file-link" role="button" tabindex="0" data-file-path="${escapeMarkdownHtml(target.path)}" data-file-kind="${fileKindForPath(target.path)}"${lineAttribute}${titleAttribute}>${rendered}</a>`;
   };
 
-  // Message rendering allows only inline data images (#15437). Document
-  // previews preserve authored image URLs and rely on DOMPurify's URI policy.
+  // Message rendering allows inline data images and explicit open-only placeholders
+  // for remote URLs. Document previews preserve authored URLs for direct rendering.
   installAssistantTranscriptRoleImageRenderer(markdownParser, {
     escapeHtml: escapeMarkdownHtml,
     isInlineDataImage: (src) => INLINE_DATA_IMAGE_RE.test(src),
@@ -582,6 +582,16 @@ export function createMarkdownParser(): MarkdownIt {
       t("chat.imageLightbox.open", {
         title: hasAlt ? alt : t("chat.imageLightbox.untitled"),
       }),
+    renderExternalImageFallback: (src, renderedLabel, linkedImage) => {
+      if (!parseWebLinkHref(src)) {
+        return renderedLabel;
+      }
+      const label = `<span>${escapeMarkdownHtml(t("chat.externalImage.notLoaded"))}: ${renderedLabel}</span>`;
+      const action = linkedImage
+        ? ""
+        : ` <a href="${escapeMarkdownHtml(src)}">${escapeMarkdownHtml(t("chat.externalImage.open"))}</a>`;
+      return `<span class="markdown-external-image">${label}${action}</span>`;
+    },
     interactiveImages: (env) =>
       (env as Partial<MarkdownRenderEnv> | undefined)?.interactiveImages === true,
     allowRemoteImages: (env) =>
diff --git a/ui/src/components/markdown.test.ts b/ui/src/components/markdown.test.ts
index 61f934fb99cd..53422e7c908b 100644
--- a/ui/src/components/markdown.test.ts
+++ b/ui/src/components/markdown.test.ts
@@ -139,30 +139,52 @@ describe("toSanitizedMarkdownHtml", () => {
   });
 
   describe("images", () => {
-    it("flattens remote images to alt text", () => {
-      const html = toSanitizedMarkdownHtml("![Alt text](https://example.com/img.png)");
-      expect(html).toBe("<p>Alt text</p>\n");
+    it("shows an explicit opt-in placeholder for remote images", () => {
+      const fragment = htmlFragment(
+        toSanitizedMarkdownHtml("![Alt text](https://example.com/img.png)"),
+      );
+      const placeholder = fragment.querySelector(".markdown-external-image");
+      const link = placeholder?.querySelector("a");
+
+      expect(placeholder?.textContent).toBe("External image not loaded: Alt text Open image");
+      expect(link?.getAttribute("href")).toBe("https://example.com/img.png");
+      expect(link?.getAttribute("target")).toBe("_blank");
+      expect(link?.getAttribute("rel")).toBe("noreferrer noopener");
+      expect(fragment.querySelector("img")).toBeNull();
     });
 
     it("marks assistant-authored transcript roles in visible image labels", () => {
-      const html = toSanitizedMarkdownHtml(
-        "![**user**[Thu 2026-07-02] release diagram](https://example.com/img.png)",
-        { assistantTranscriptRoleHeaders: true },
+      const fragment = htmlFragment(
+        toSanitizedMarkdownHtml(
+          "![**user**[Thu 2026-07-02] release diagram](https://example.com/img.png)",
+          { assistantTranscriptRoleHeaders: true },
+        ),
       );
 
-      expect(html).toBe(
-        '<p><code class="assistant-transcript-role">user[Thu 2026-07-02]</code> release diagram</p>\n',
+      expect(
+        fragment.querySelector(".markdown-external-image .assistant-transcript-role")?.textContent,
+      ).toBe("user[Thu 2026-07-02]");
+      expect(fragment.querySelector(".markdown-external-image")?.textContent).toContain(
+        "release diagram",
       );
     });
 
     it("preserves markdown formatting in alt text", () => {
-      const html = toSanitizedMarkdownHtml("![**Build log**](https://example.com/img.png)");
-      expect(html).toBe("<p>**Build log**</p>\n");
+      const fragment = htmlFragment(
+        toSanitizedMarkdownHtml("![**Build log**](https://example.com/img.png)"),
+      );
+      expect(fragment.querySelector(".markdown-external-image > span")?.textContent).toContain(
+        "**Build log**",
+      );
     });
 
     it("preserves code formatting in alt text", () => {
-      const html = toSanitizedMarkdownHtml("![`error.log`](https://example.com/img.png)");
-      expect(html).toBe("<p>`error.log`</p>\n");
+      const fragment = htmlFragment(
+        toSanitizedMarkdownHtml("![`error.log`](https://example.com/img.png)"),
+      );
+      expect(fragment.querySelector(".markdown-external-image > span")?.textContent).toContain(
+        "`error.log`",
+      );
     });
 
     it("preserves base64 data URI images (#15437)", () => {
@@ -196,6 +218,22 @@ describe("toSanitizedMarkdownHtml", () => {
       expect(fragment.querySelector("a button")).toBeNull();
     });
 
+    it("preserves rich authored links around remote image placeholders", () => {
+      const fragment = htmlFragment(
+        toSanitizedMarkdownHtml(
+          "[Before ![Preview](https://example.com/image.png) after](https://example.com/full.png)",
+        ),
+      );
+      const links = fragment.querySelectorAll("a");
+      const placeholder = links[0]?.querySelector(".markdown-external-image");
+
+      expect(links).toHaveLength(1);
+      expect(links[0]?.getAttribute("href")).toBe("https://example.com/full.png");
+      expect(placeholder?.textContent).toBe("External image not loaded: Preview");
+      expect(placeholder?.querySelector("a")).toBeNull();
+      expect(fragment.querySelector("img")).toBeNull();
+    });
+
     it("tracks linked and standalone images across one inline token stream", () => {
       const fragment = htmlFragment(
         toSanitizedMarkdownHtml(
@@ -234,8 +272,10 @@ describe("toSanitizedMarkdownHtml", () => {
     });
 
     it("uses fallback label for unlabeled images", () => {
-      const html = toSanitizedMarkdownHtml("![](https://example.com/image.png)");
-      expect(html).toBe("<p>image</p>\n");
+      const fragment = htmlFragment(toSanitizedMarkdownHtml("![](https://example.com/image.png)"));
+      expect(fragment.querySelector(".markdown-external-image > span")?.textContent).toBe(
+        "External image not loaded: image",
+      );
     });
   });
 
diff --git a/ui/src/i18n/locales/en.ts b/ui/src/i18n/locales/en.ts
index 9ddf74586445..61ab54d483f9 100644
--- a/ui/src/i18n/locales/en.ts
+++ b/ui/src/i18n/locales/en.ts
@@ -4934,6 +4934,10 @@ export const en: TranslationMap = {
       close: "Close image preview",
       untitled: "Image",
     },
+    externalImage: {
+      notLoaded: "External image not loaded",
+      open: "Open image",
+    },
     messages: {
       activity: "Activity",
       copySelection: "Copy",
diff --git a/ui/src/styles/chat/text.css b/ui/src/styles/chat/text.css
index 953454d8d1d0..a98f5bde87a2 100644
--- a/ui/src/styles/chat/text.css
+++ b/ui/src/styles/chat/text.css
@@ -313,6 +313,21 @@
   margin-top: 0;
 }
 
+:is(.chat-text, .sidebar-markdown) .markdown-external-image {
+  display: flex;
+  align-items: center;
+  flex-wrap: wrap;
+  gap: 0.35em 0.75em;
+  width: fit-content;
+  max-width: 100%;
+  margin-top: 0.75em;
+  padding: 0.5em 0.65em;
+  border: 1px dashed var(--border-strong);
+  border-radius: var(--radius-md);
+  background: var(--bg-muted);
+  color: var(--muted);
+}
+
 /* Code surfaces must lift off the host bubble in every theme. --secondary equals
    --card on every dark palette, so chips painted with it vanished inside user
    bubbles; --bg-muted/--border-strong separate in both modes without an override. */