diff --git a/packages/views/editor/attachment.test.tsx b/packages/views/editor/attachment.test.tsx
index d122b2263c..d18beff574 100644
--- a/packages/views/editor/attachment.test.tsx
+++ b/packages/views/editor/attachment.test.tsx
@@ -335,7 +335,7 @@ describe("Attachment — image dispatch", () => {
     // through to the durable markdown_url instead.
     configStore.setState({ cdnDomain: "cdn.example.test", cdnSigned: true });
     const id = "11111111-2222-3333-4444-555555555555";
-    const markdownUrl = `https://multica-api.copilothub.ai/api/attachments/${id}/download`;
+    const markdownUrl = `/api/attachments/${id}/download`;
     const att = makeRecord({
       id,
       url: "https://cdn.example.test/uploads/ws/shot.png",
@@ -362,6 +362,44 @@ describe("Attachment — image dispatch", () => {
     expect(getAttachmentMock).not.toHaveBeenCalled();
   });
 
+  it("re-signs a cross-origin API image URL in the web editor", async () => {
+    // The web app normally uses the same-origin /api proxy, so getBaseUrl is
+    // empty. A self-hosted server can still persist an absolute markdown_url
+    // on a different origin, though. Native <img> loading cannot rely on the
+    // app session cookie being accepted by that host, while an authenticated
+    // metadata request can return a freshly signed storage URL.
+    configStore.setState({ cdnDomain: "cdn.example.test", cdnSigned: true });
+    const id = "11111111-2222-3333-4444-555555555555";
+    const markdownUrl = `https://api.example.test/api/attachments/${id}/download`;
+    const signed =
+      "https://cdn.example.test/uploads/ws/shot.png?Signature=fresh&Key-Pair-Id=K";
+    resolverState.attachments = [
+      makeRecord({
+        id,
+        url: "https://cdn.example.test/uploads/ws/shot.png",
+        markdown_url: markdownUrl,
+        download_url: `/api/attachments/${id}/download`,
+      }),
+    ];
+    getAttachmentMock.mockResolvedValue(makeRecord({ id, download_url: signed }));
+
+    renderWithQuery(
+      <Attachment
+        attachment={{
+          kind: "url",
+          url: markdownUrl,
+          filename: "shot.png",
+          forceKind: "image",
+        }}
+      />,
+    );
+
+    await waitFor(() => {
+      expect(document.querySelector("img")?.getAttribute("src")).toBe(signed);
+    });
+    expect(getAttachmentMock).toHaveBeenCalledWith(id);
+  });
+
   it("re-signs the inline media URL through getAttachment on token-mode clients (MUL-3254)", async () => {
     // Desktop / mobile webview: file:// document origin, Bearer-token auth.
     // The auth-gated /api/attachments/<id>/download endpoint 401s as a
diff --git a/packages/views/editor/attachment.tsx b/packages/views/editor/attachment.tsx
index 534579d057..ceaeb537be 100644
--- a/packages/views/editor/attachment.tsx
+++ b/packages/views/editor/attachment.tsx
@@ -321,11 +321,12 @@ const RESIGN_STALE_MS = 20 * 60 * 1000;
 // endpoint (e.g. a reopened issue draft, whose persisted record deliberately
 // strips the short-lived signed `download_url`). That endpoint needs
 // credentials: web loads it because the session cookie rides on the <img>
-// request (same-site), but Desktop's file:// renderer and the mobile webview
-// are cross-site — no cookie is attached and the Bearer token cannot be put
-// on a native resource fetch, so the image 401s. Those clients are exactly
-// the ones with a non-empty `api.getBaseUrl()` (no same-origin /api proxy),
-// which is the existing platform signal `absolutizeMediaURL` keys off.
+// request when it is genuinely same-origin. Desktop's file:// renderer, the
+// mobile webview, and split-origin web deployments cannot rely on that: no
+// cookie is attached and the Bearer token cannot be put on a native resource
+// fetch, so the image 401s. Desktop/mobile expose a non-empty
+// `api.getBaseUrl()`; web can also hit this path when the server emits an
+// absolute markdown URL whose origin differs from the current page.
 //
 // For them, fetch fresh attachment metadata through the authenticated API —
 // the same re-sign the click-time download path already does — and swap in
@@ -338,11 +339,21 @@ function useResignedInlineMediaURL(
 ): string {
   const idFromPickedUrl = attachmentIdFromDownloadURL(pickedUrl);
   const resignAttachmentId = attachmentId ?? idFromPickedUrl;
+  const isCrossOriginWebURL = (() => {
+    if (!/^https?:\/\//i.test(pickedUrl) || typeof window === "undefined") {
+      return false;
+    }
+    try {
+      return new URL(pickedUrl).origin !== window.location.origin;
+    } catch {
+      return false;
+    }
+  })();
   const needsResign =
     !!resignAttachmentId &&
     !!pickedUrl &&
     idFromPickedUrl !== undefined &&
-    (api.getBaseUrl?.() ?? "") !== "";
+    ((api.getBaseUrl?.() ?? "") !== "" || isCrossOriginWebURL);
 
   const { data: fresh } = useQuery({
     queryKey: ["attachment-inline-resign", resignAttachmentId],