diff --git a/hub/src/web/server.ts b/hub/src/web/server.ts
index 6cb156cc..b4dbf4eb 100644
--- a/hub/src/web/server.ts
+++ b/hub/src/web/server.ts
@@ -234,7 +234,7 @@ export async function startWebServer(options: {
         hostname: configuration.listenHost,
         port: configuration.listenPort,
         idleTimeout: Math.max(30, socketHandler.idleTimeout),
-        maxRequestBodySize: socketHandler.maxRequestBodySize,
+        maxRequestBodySize: Math.max(socketHandler.maxRequestBodySize, 68 * 1024 * 1024),
         websocket: socketHandler.websocket,
         fetch: (req, server) => {
             const url = new URL(req.url)
diff --git a/web/src/components/AssistantChat/AttachmentItem.tsx b/web/src/components/AssistantChat/AttachmentItem.tsx
index 4f7e2668..af08ff4f 100644
--- a/web/src/components/AssistantChat/AttachmentItem.tsx
+++ b/web/src/components/AssistantChat/AttachmentItem.tsx
@@ -43,7 +43,8 @@ export function AttachmentItem() {
                     <ErrorIcon />
                 </span>
             ) : null}
-            <span className="max-w-[150px] truncate">{name}</span>
+            <span className={`max-w-[150px] truncate ${isError ? 'text-red-500 line-through' : ''}`}>{name}</span>
+            {isError ? <span className="text-xs text-red-500 whitespace-nowrap">Upload failed</span> : null}
             <AttachmentPrimitive.Remove
                 className="ml-auto flex h-5 w-5 items-center justify-center rounded text-[var(--app-hint)] transition-colors hover:text-[var(--app-fg)]"
                 aria-label="Remove attachment"