diff --git a/apps/web/src/components/chat/MessagesTimeline.test.tsx b/apps/web/src/components/chat/MessagesTimeline.test.tsx
index 2dacb5bd359605e913fe8ad1d45637cc906d4fea..42a12e60827a6f8bfcdede38a34b80417c80cd1a 100644
--- a/apps/web/src/components/chat/MessagesTimeline.test.tsx
+++ b/apps/web/src/components/chat/MessagesTimeline.test.tsx
@@ -1473,7 +1473,7 @@ describe("MessagesTimeline", () => {
       />,
     );
 
-    expect(markup).toContain("lucide-x");
+    expect(markup).toContain("lucide-circle-alert");
     expect(markup).toContain('aria-label="Tool call failed"');
     // Ordinary tool failures render muted, not red.
     expect(markup).not.toContain("text-destructive");
@@ -1511,7 +1511,7 @@ describe("MessagesTimeline", () => {
       />,
     );
 
-    expect(markup).toContain("lucide-x");
+    expect(markup).toContain("lucide-circle-alert");
     expect(markup).toContain("text-destructive");
   });
 });
diff --git a/apps/web/src/components/chat/MessagesTimeline.tsx b/apps/web/src/components/chat/MessagesTimeline.tsx
index b207ebc73689038bc1a539f66a0da86cc2d72a1e..2a220c87e1b03a599aa26ab40ee6de65aa6b679f 100644
--- a/apps/web/src/components/chat/MessagesTimeline.tsx
+++ b/apps/web/src/components/chat/MessagesTimeline.tsx
@@ -1579,7 +1579,7 @@ function LiveActivityContent({
   announceFailure?: boolean;
   highlighted?: boolean;
 }) {
-  const resolvedIconName = failed ? "x" : iconName;
+  const resolvedIconName = failed ? "circle-alert" : iconName;
 
   return (
     <div
@@ -2554,7 +2554,7 @@ const PlainWorkEntryRow = memo(function PlainWorkEntryRow(props: {
   const showWarningIndicator = workEntry.sourceActivityKind === "runtime.warning";
   const showFailedIndicator = workEntryDisplayIndicatesToolFailure(workEntry);
   const entryIconName =
-    showWarningIndicator || showFailedIndicator ? "x" : workEntryIconName(workEntry);
+    showWarningIndicator || showFailedIndicator ? "circle-alert" : workEntryIconName(workEntry);
   const displayText = workEntryPreview(workEntry, workspaceRoot) ?? toolWorkEntryHeading(workEntry);
   const expandedBody = buildToolCallExpandedBody(workEntry, workspaceRoot);
   const canExpand = expandedBody !== null;