From ad4d910aefe296031e42efe0abfec0b6ccdf14ef Mon Sep 17 00:00:00 2001
From: Mohamed Boudra <boudra.moha@gmail.com>
Date: Thu, 15 Oct 2026 16:55:15 +0200
Subject: [PATCH] fix(markdown): retry transient image decode failures

---
 .../src/components/markdown/image-decoding.ts | 18 ++++++++++++++++
 .../app/src/components/markdown/images.ts     | 17 ++++++---------
 .../src/components/markdown/renderer.test.ts  | 21 +++++++++++++++++++
 3 files changed, 45 insertions(+), 11 deletions(-)
 create mode 100644 packages/app/src/components/markdown/image-decoding.ts

diff --git a/packages/app/src/components/markdown/image-decoding.ts b/packages/app/src/components/markdown/image-decoding.ts
new file mode 100644
index 0000000000..9750d7d6c0
--- /dev/null
+++ b/packages/app/src/components/markdown/image-decoding.ts
@@ -0,0 +1,18 @@
+type ImageDecoder = (
+  uri: string,
+  success: (width: number, height: number) => void,
+  failure: (error: unknown) => void,
+) => void;
+
+export function decodeMarkdownImage(uri: string, decode: ImageDecoder): Promise<true> {
+  return new Promise((resolve, reject) => {
+    decode(
+      uri,
+      (width, height) => {
+        if (width > 0 && height > 0) resolve(true);
+        else reject(new Error("Image has no decodable dimensions"));
+      },
+      reject,
+    );
+  });
+}
diff --git a/packages/app/src/components/markdown/images.ts b/packages/app/src/components/markdown/images.ts
index 37559fa3e9..c0832055a6 100644
--- a/packages/app/src/components/markdown/images.ts
+++ b/packages/app/src/components/markdown/images.ts
@@ -15,6 +15,7 @@ import type { DaemonClient } from "@getpaseo/client/internal/daemon-client";
 import type { AttachmentMetadata } from "@/attachments/types";
 import { resolveMarkdownPreviewImageSource } from "./image-source";
 import { prepareMarkdownSource } from "./source";
+import { decodeMarkdownImage } from "./image-decoding";
 
 const urls = createAssistantImageAcquisitionCache<{ uri: string; attachment: AttachmentMetadata }>({
   capacity: 500,
@@ -99,11 +100,15 @@ export function useMarkdownSource(text: string, context: MarkdownImageContext) {
   const decoded = useFetchQueries(
     displayUrls.map((uri, index) => ({
       queryKey: ["markdownImageDecode", occurrenceKey, uri ?? sources[index]],
+      refetchOnReconnect: true,
       enabled: uri !== undefined,
       immutableWhen: () => true,
       dataShape: "value",
       gcTime: 0,
-      queryFn: () => (uri ? canDecodeImage(uri) : Promise.resolve(false)),
+      queryFn: () => {
+        if (!uri) throw new Error("No image URL to decode");
+        return decodeMarkdownImage(uri, Image.getSize);
+      },
     })),
   );
   const unavailableImages = new Set(
@@ -118,13 +123,3 @@ export function useMarkdownSource(text: string, context: MarkdownImageContext) {
     imageSources: Object.fromEntries([...resolved].map(([source, url]) => [url, source])),
   };
 }
-
-function canDecodeImage(uri: string): Promise<boolean> {
-  return new Promise((resolve) => {
-    Image.getSize(
-      uri,
-      (width, height) => resolve(width > 0 && height > 0),
-      () => resolve(false),
-    );
-  });
-}
diff --git a/packages/app/src/components/markdown/renderer.test.ts b/packages/app/src/components/markdown/renderer.test.ts
index 214193d850..560ae23973 100644
--- a/packages/app/src/components/markdown/renderer.test.ts
+++ b/packages/app/src/components/markdown/renderer.test.ts
@@ -1,3 +1,5 @@
+import { QueryClient } from "@tanstack/react-query";
+import { decodeMarkdownImage } from "./image-decoding";
 import { createElement } from "react";
 import { MarkdownRendererFrame } from "./frame";
 import { describe, expect, it } from "vitest";
@@ -348,3 +350,22 @@ it("preserves literal Markdown punctuation in unsupported and failed image label
     ),
   ).toBe(label);
 });
+
+it("retries transient image decoding failures instead of caching an unavailable image", async () => {
+  const client = new QueryClient();
+  let attempts = 0;
+  const decoded = await client.fetchQuery({
+    queryKey: ["markdownImageDecode", "transient.png"],
+    retry: 1,
+    retryDelay: 0,
+    queryFn: () =>
+      decodeMarkdownImage("transient.png", (_uri, success, failure) => {
+        attempts += 1;
+        if (attempts === 1) failure(new Error("temporarily unavailable"));
+        else success(20, 20);
+      }),
+  });
+  expect(decoded).toBe(true);
+  expect(attempts).toBe(2);
+  client.clear();
+});