Sequence tools after same-message patches; report tool failures to the room

packages/ai-bot/tests/prompt-construction-test.ts

@@ -2763,6 +2763,115 @@ Attached Files (files with newer versions don't show their content):
     assert.equal(messageText(result[5]).trim(), expected.trim());
   });
 
+  test('a later applied result supersedes an earlier failed result for the same request', async () => {
+    // A tool can fail and then succeed on a user Retry; both result events
+    // stay in the room forever. The prompt must reflect the latest one, or
+    // the model is permanently told the call failed and may re-issue it.
+    const history: DiscreteMatrixEvent[] = [
+      {
+        type: 'm.room.message',
+        room_id: 'room-id-1',
+        sender: '@user:localhost',
+        content: {
+          body: 'set the title',
+          msgtype: APP_BOXEL_MESSAGE_MSGTYPE,
+          format: 'org.matrix.custom.html',
+          data: { context: { tools: [], functions: [] } },
+        },
+        origin_server_ts: 1722242847000,
+        unsigned: { age: 1000, transaction_id: 't0' },
+        event_id: 'user-event-id-1',
+        status: EventStatus.SENT,
+      },
+      {
+        type: 'm.room.message',
+        room_id: 'room-id-1',
+        sender: '@aibot:localhost',
+        content: {
+          body: 'Setting the title',
+          msgtype: APP_BOXEL_MESSAGE_MSGTYPE,
+          format: 'org.matrix.custom.html',
+          data: { context: { functions: [] } },
+          [APP_BOXEL_TOOL_REQUESTS_KEY]: [
+            {
+              id: 'retried-tool-call-id-1',
+              name: 'patchCardInstance',
+              arguments: JSON.stringify({
+                attributes: { description: 'Set the title' },
+              }),
+            },
+          ],
+        },
+        origin_server_ts: 1722242849000,
+        unsigned: { age: 900, transaction_id: 't1' },
+        event_id: 'retried-command-event-id-1',
+        status: EventStatus.SENT,
+      },
+      {
+        type: APP_BOXEL_TOOL_RESULT_EVENT_TYPE,
+        room_id: 'room-id-1',
+        sender: '@user:localhost',
+        content: {
+          'm.relates_to': {
+            event_id: 'retried-command-event-id-1',
+            rel_type: APP_BOXEL_TOOL_RESULT_REL_TYPE,
+            key: 'failed',
+          },
+          msgtype: APP_BOXEL_TOOL_RESULT_WITH_NO_OUTPUT_MSGTYPE,
+          commandRequestId: 'retried-tool-call-id-1',
+          failureReason: 'store exploded',
+          data: { context: { tools: [], functions: [] } },
+        },
+        origin_server_ts: 1722242853000,
+        unsigned: { age: 800, transaction_id: 't2' },
+        event_id: 'failed-result-id-1',
+        status: EventStatus.SENT,
+      },
+      {
+        type: APP_BOXEL_TOOL_RESULT_EVENT_TYPE,
+        room_id: 'room-id-1',
+        sender: '@user:localhost',
+        content: {
+          'm.relates_to': {
+            event_id: 'retried-command-event-id-1',
+            rel_type: APP_BOXEL_TOOL_RESULT_REL_TYPE,
+            key: 'applied',
+          },
+          msgtype: APP_BOXEL_TOOL_RESULT_WITH_NO_OUTPUT_MSGTYPE,
+          commandRequestId: 'retried-tool-call-id-1',
+          data: { context: { tools: [], functions: [] } },
+        },
+        origin_server_ts: 1722242857000,
+        unsigned: { age: 700, transaction_id: 't3' },
+        event_id: 'applied-result-id-1',
+        status: EventStatus.SENT,
+      },
+    ];
+    const result = await buildPromptForModel(
+      history,
+      '@aibot:localhost',
+      [],
+      [],
+      [],
+      fakeMatrixClient,
+    );
+    let toolMessages = result.filter((m) => m.role === 'tool');
+    assert.equal(toolMessages.length, 1, 'one tool message per request');
+    assert.equal(
+      (toolMessages[0] as { tool_call_id?: string }).tool_call_id,
+      'retried-tool-call-id-1',
+    );
+    let content = messageText(toolMessages[0]);
+    assert.true(
+      content.includes('executed'),
+      `the retried call reads as executed, got: ${content}`,
+    );
+    assert.false(
+      content.includes('failed'),
+      `no stale failure text survives the retry, got: ${content}`,
+    );
+  });
+
   test('pairs a pre-rename request/result (legacy wire keys) with the same tool_call_id', async () => {
     // A room whose history predates the command → tool rename replays events
     // with the legacy spellings forever; prompt assembly must pair them

packages/host/app/components/matrix/room-message-tool.gts

@@ -225,6 +225,13 @@ export default class RoomMessageTool extends Component<Signature> {
     return this.matrixService.failedToolState.get(toolRequest.id);
   }
 
+  // Execution failure reported through a room event (as opposed to
+  // failedToolState, which is this tab's in-memory state for a failure it
+  // produced itself).
+  private get failedToolCallState() {
+    return this.args.messageTool.status === 'failed' && !this.failedToolState;
+  }
+
   private get invalidToolCallState() {
     return (
       this.args.messageTool.status === 'invalid' &&
@@ -237,7 +244,11 @@ export default class RoomMessageTool extends Component<Signature> {
   }
 
   private get hasFailedState() {
-    return !!(this.failedToolState || this.didFailCorrectnessCheck);
+    return !!(
+      this.failedToolState ||
+      this.failedToolCallState ||
+      this.didFailCorrectnessCheck
+    );
   }
 
   <template>
@@ -301,6 +312,19 @@ export default class RoomMessageTool extends Component<Signature> {
             <Alert.Messages @messages={{array this.failedToolState.message}} />
             <Alert.Action @action={{@runCommand}} @actionName='Retry' />
           </Alert>
+        {{else if this.failedToolCallState}}
+          <Alert @type='error' as |Alert|>
+            <Alert.Messages
+              @messages={{array
+                (if
+                  @messageTool.failureReason
+                  @messageTool.failureReason
+                  'Tool call failed.'
+                )
+              }}
+            />
+            <Alert.Action @action={{@runCommand}} @actionName='Retry' />
+          </Alert>
         {{else if this.invalidToolCallState}}
           <Alert @type='warning' as |Alert|>
             <Alert.Messages @messages={{array @messageTool.failureReason}} />

packages/host/app/lib/matrix-classes/message-builder.ts

@@ -371,23 +371,33 @@ export default class MessageBuilder {
     message: Message,
     toolRequest: Partial<ToolRequest>,
   ) {
-    let toolResultEvent =
-      this.builderContext.toolResultEvent ??
-      (this.builderContext.events.find((e: any) => {
-        let r = e.content['m.relates_to'];
-        // Correlate the result to its command by commandRequestId (the
-        // globally unique LLM tool-call id), not by the result's
-        // m.relates_to.event_id. A reload strips the m.replace edits and loads
-        // only the original event, so the result's link id — pointing at the
-        // final edit — matches no loaded event. commandRequestId is stable
-        // across edits and present on every one, so it resolves the command on
-        // both the live and reload paths.
-        return (
+    let toolResultEvent = this.builderContext.toolResultEvent;
+    if (!toolResultEvent) {
+      // Correlate the result to its command by commandRequestId (the
+      // globally unique LLM tool-call id), not by the result's
+      // m.relates_to.event_id. A reload strips the m.replace edits and loads
+      // only the original event, so the result's link id — pointing at the
+      // final edit — matches no loaded event. commandRequestId is stable
+      // across edits and present on every one, so it resolves the command on
+      // both the live and reload paths.
+      //
+      // Scan newest-first: a request can have several result events (a
+      // 'failed' first attempt, an 'applied' retry) and the latest one is
+      // the call's actual outcome.
+      let events = this.builderContext.events;
+      for (let i = events.length - 1; i >= 0; i--) {
+        let e = events[i] as any;
+        let r = e.content?.['m.relates_to'];
+        if (
           isToolResultEventType(e.type) &&
           isToolResultRelType(r?.rel_type) &&
           e.content.commandRequestId === toolRequest.id
-        );
-      }) as ToolResultEvent | undefined);
+        ) {
+          toolResultEvent = e as ToolResultEvent;
+          break;
+        }
+      }
+    }
 
     // ai-bot ran this one itself (e.g. readRealmFile), so the host never
     // resolves a command class or runs it. Skip the skill lookup below — it's

packages/host/app/lib/matrix-classes/message-tool.ts

@@ -18,7 +18,7 @@ import type { Message } from './message';
 import type { CardDef } from '@cardstack/base/card-api';
 import type { SerializedFile } from '@cardstack/base/file-api';
 
-type ToolCallStatus = 'applied' | 'ready' | 'applying' | 'invalid';
+type ToolCallStatus = 'applied' | 'ready' | 'applying' | 'invalid' | 'failed';
 
 export default class MessageTool {
   @tracked toolRequest: Partial<ToolRequest>;