From c15735dd8894f829ce396c922ce4b5a48073f05a Mon Sep 17 00:00:00 2001
From: maria <maria@kuuro.net>
Date: Wed, 2 Sep 2026 01:19:48 -0400
Subject: [PATCH] fix(chat): replace failed tools with thinking (#9165)

Co-authored-by: maria-rcks <254055478+maria-rcks@users.noreply.github.com>
---
 .../components/chat/MessagesTimeline.logic.test.ts    |  9 ++++++++-
 .../web/src/components/chat/MessagesTimeline.logic.ts | 11 ++++++++---
 2 files changed, 16 insertions(+), 4 deletions(-)

diff --git a/apps/web/src/components/chat/MessagesTimeline.logic.test.ts b/apps/web/src/components/chat/MessagesTimeline.logic.test.ts
index 83d55e285e986539f9df3ca3f765078120ba7c11..de6632093047799e2a06bd2d45865b0a62f09370 100644
--- a/apps/web/src/components/chat/MessagesTimeline.logic.test.ts
+++ b/apps/web/src/components/chat/MessagesTimeline.logic.test.ts
@@ -1411,7 +1411,9 @@ describe("deriveMessagesTimelineRows", () => {
   );
 
   it("reuses one activity row for initial thinking and the latest tool", () => {
-    const deriveRows = (toolLifecycleStatus: "inProgress" | "completed" | "declined" | null) =>
+    const deriveRows = (
+      toolLifecycleStatus: "inProgress" | "completed" | "failed" | "declined" | null,
+    ) =>
       deriveMessagesTimelineRows({
         timelineEntries:
           toolLifecycleStatus === null
@@ -1430,6 +1432,7 @@ describe("deriveMessagesTimelineRows", () => {
                     requestKind: "command",
                     tone: "tool" as const,
                     toolLifecycleStatus,
+                    ...(toolLifecycleStatus === "inProgress" ? { detail: "exit code 1" } : {}),
                   },
                 },
               ],
@@ -1448,6 +1451,7 @@ describe("deriveMessagesTimelineRows", () => {
     const initialRows = deriveRows(null);
     const runningRows = deriveRows("inProgress");
     const completedRows = deriveRows("completed");
+    const failedRows = deriveRows("failed");
     const declinedRows = deriveRows("declined");
     const initialActivityRow = initialRows.find((row) => row.id === "live-activity-row");
     const runningActivityRow = runningRows.find((row) => row.id === "live-activity-row");
@@ -1456,11 +1460,14 @@ describe("deriveMessagesTimelineRows", () => {
     expect(initialActivityRow).toMatchObject({ kind: "thinking" });
     expect(runningActivityRow).toMatchObject({ kind: "work-live", active: true });
     expect(completedActivityRow).toMatchObject({ kind: "work-live", active: true });
+    expect(failedRows.some((row) => row.kind === "work-live")).toBe(false);
+    expect(failedRows.at(-1)).toMatchObject({ kind: "thinking", id: "live-activity-row" });
     expect(declinedRows.find((row) => row.kind === "work-live")).toMatchObject({ active: false });
     expect(declinedRows.at(-1)).toMatchObject({ kind: "thinking", id: "live-activity-row" });
     expect(initialRows.filter((row) => row.id === "live-activity-row")).toHaveLength(1);
     expect(runningRows.filter((row) => row.id === "live-activity-row")).toHaveLength(1);
     expect(completedRows.filter((row) => row.id === "live-activity-row")).toHaveLength(1);
+    expect(failedRows.filter((row) => row.id === "live-activity-row")).toHaveLength(1);
     expect(declinedRows.filter((row) => row.id === "live-activity-row")).toHaveLength(1);
   });
 
diff --git a/apps/web/src/components/chat/MessagesTimeline.logic.ts b/apps/web/src/components/chat/MessagesTimeline.logic.ts
index 41ec77b1eb5a843d493a9801c09ffe42069d5718..7cea3803827daad14d62e6e40510dcf36ed9ebb5 100644
--- a/apps/web/src/components/chat/MessagesTimeline.logic.ts
+++ b/apps/web/src/components/chat/MessagesTimeline.logic.ts
@@ -691,13 +691,18 @@ export function deriveMessagesTimelineRows(input: {
   const latestRunningToolEntry = visibleActiveToolEntries.findLast((entry) =>
     workEntryIsActiveTurnActivity(entry.entry),
   );
+  const latestToolFailed =
+    latestRunningToolEntry === undefined &&
+    latestVisibleToolEntry !== undefined &&
+    latestVisibleToolEntry.entry.toolLifecycleStatus !== "declined" &&
+    workEntryDisplayIndicatesToolFailure(latestVisibleToolEntry.entry);
   const latestToolKeepsActivityLive =
     latestRunningToolEntry !== undefined ||
     (latestVisibleToolEntry !== undefined &&
       workEntryIndicatesToolSuccess(latestVisibleToolEntry.entry));
   const activeWorkPlacementEntryId = latestVisibleToolEntry?.id;
   const activeWorkRow =
-    activeWorkAnchor && latestVisibleToolEntry
+    activeWorkAnchor && latestVisibleToolEntry && !latestToolFailed
       ? (() => {
           const groupId = workGroupId(activeWorkAnchor.id, activeWorkAnchor.entry);
           return {
@@ -715,7 +720,7 @@ export function deriveMessagesTimelineRows(input: {
         })()
       : null;
   const activeWorkEntryIds = new Set(
-    activeWorkRow === null ? [] : activeToolEntries.map((entry) => entry.id),
+    activeWorkRow !== null || latestToolFailed ? activeToolEntries.map((entry) => entry.id) : [],
   );
   const appendWorkingRow = () => {
     nextRows.push({
@@ -912,7 +917,7 @@ export function deriveMessagesTimelineRows(input: {
   if (input.isWorking && activeTurnHeaderIndex === input.timelineEntries.length) {
     appendWorkingRow();
   }
-  if (input.isWorking && !hasActivityRow) {
+  if (input.isWorking && (!hasActivityRow || latestToolFailed)) {
     nextRows.push({
       kind: "thinking",
       id: LIVE_ACTIVITY_ROW_ID,
-- 
2.54.0