diff --git a/src/app/components/message/content/ImageContent.tsx b/src/app/components/message/content/ImageContent.tsx
index 47ece05e1..c085e8479 100644
--- a/src/app/components/message/content/ImageContent.tsx
+++ b/src/app/components/message/content/ImageContent.tsx
@@ -33,6 +33,7 @@ import { useMediaAuthentication } from '../../../hooks/useMediaAuthentication';
 import { ModalWide } from '../../../styles/Modal.css';
 import { validBlurHash } from '../../../utils/blurHash';
 import { useNearViewport } from '../../../hooks/useNearViewport';
+import { whenMediaAuthReady } from '../../../../sw-session';
 
 type RenderViewerProps = {
   src: string;
@@ -115,13 +116,24 @@ export const ImageContent = as<'div', ImageContentProps>(
     const handleLoad = () => {
       setLoad(true);
     };
+    // An image requested before the service worker controls the page goes out
+    // without the access token and fails (first visit, just after an update).
+    // Retry once by itself when that's ready; only then offer "Retry".
+    const [attempt, setAttempt] = useState(0);
+    const autoRetried = useRef(false);
     const handleError = () => {
       setLoad(false);
+      if (!autoRetried.current && !encInfo) {
+        autoRetried.current = true;
+        whenMediaAuthReady().then(() => setAttempt((n) => n + 1));
+        return;
+      }
       setError(true);
     };
 
     const handleRetry = () => {
       setError(false);
+      setAttempt((n) => n + 1);
       loadSrc();
     };
 
@@ -182,7 +194,7 @@ export const ImageContent = as<'div', ImageContentProps>(
           </Box>
         )}
         {srcState.status === AsyncStatus.Success && (
-          <Box className={classNames(css.AbsoluteContainer, blurred && css.Blur)}>
+          <Box key={attempt} className={classNames(css.AbsoluteContainer, blurred && css.Blur)}>
             {renderImage({
               alt: body,
               title: body,
diff --git a/src/sw-session.ts b/src/sw-session.ts
index e4d2672da..a094f45db 100644
--- a/src/sw-session.ts
+++ b/src/sw-session.ts
@@ -9,3 +9,25 @@ export function pushSessionToSW(baseUrl?: string, accessToken?: string, userId?:
     userId,
   });
 }
+
+/**
+ * Resolves once media requests can carry the session: immediately-ish when a
+ * service worker already controls the page, otherwise when one takes control
+ * (first visit / just updated) or after `timeoutMs`. Used to retry a media
+ * load that raced the worker's activation and went out without a token.
+ */
+export function whenMediaAuthReady(timeoutMs = 3000): Promise<void> {
+  return new Promise((resolve) => {
+    const sw = 'serviceWorker' in navigator ? navigator.serviceWorker : undefined;
+    if (!sw || sw.controller) {
+      window.setTimeout(resolve, 500);
+      return;
+    }
+    const done = () => {
+      sw.removeEventListener('controllerchange', done);
+      resolve();
+    };
+    sw.addEventListener('controllerchange', done);
+    window.setTimeout(done, timeoutMs);
+  });
+}