feat(mothership): enrich opaque tool errors with actionable context

Bare AbortSignal.timeout / abort messages ("The operation timed out.")
reaching the model-facing tool result now carry the tool name, elapsed
time, and the may-have-landed honesty with a verify-before-retry
suggestion. Informative messages pass through untouched.

Claude-Session: https://claude.ai/code/session_01CgaxNAaeD3taGdghbXn17w

Author: Sg312

apps/sim/lib/mothership/request/tools/enrich-error.test.ts

@@ -0,0 +1,30 @@
+/**
+ * @vitest-environment node
+ */
+import { describe, expect, it } from 'vitest'
+import { enrichOpaqueToolError } from '@/lib/mothership/request/tools/executor'
+
+describe('enrichOpaqueToolError', () => {
+  it('wraps the bare AbortSignal.timeout message with tool context', () => {
+    const out = enrichOpaqueToolError(
+      'The operation timed out.',
+      'run_workflow',
+      Date.now() - 90_000
+    )
+    expect(out).toContain('run_workflow timed out after ~90s')
+    expect(out).toContain('read the affected resource back')
+  })
+
+  it('wraps bare abort messages', () => {
+    expect(enrichOpaqueToolError('This operation was aborted', 'run_code', undefined)).toContain(
+      'run_code timed out'
+    )
+  })
+
+  it('leaves informative messages untouched', () => {
+    const informative =
+      "Tool 'run_code' timed out after 300s on the Sim executor and was abandoned."
+    expect(enrichOpaqueToolError(informative, 'run_code', Date.now())).toBe(informative)
+    expect(enrichOpaqueToolError('Invalid API key', 'sim_cli', Date.now())).toBe('Invalid API key')
+  })
+})

apps/sim/lib/mothership/request/tools/executor.ts

@@ -267,6 +267,32 @@ export function pendingToolWaitBudgetMs(
   return toolWatchdogTimeoutMs(toolCall?.name)
 }
 
+/**
+ * Bare timeout/abort messages (AbortSignal.timeout's "The operation timed out.",
+ * a DOMException's "This operation was aborted") strip everything the model
+ * needs to reason about the failure. Name the tool, the elapsed time, and the
+ * honest uncertainty; leave every informative message untouched.
+ */
+export function enrichOpaqueToolError(
+  message: string,
+  toolName: string,
+  startTimeMs: number | undefined
+): string {
+  if (
+    !/^(the operation timed out\.?|this operation was aborted\.?|timeout|aborted)$/i.test(
+      message.trim()
+    )
+  ) {
+    return message
+  }
+  const elapsed = startTimeMs ? ` after ~${Math.round((Date.now() - startTimeMs) / 1000)}s` : ''
+  return (
+    `${toolName} timed out${elapsed} inside its handler ("${message}"). ` +
+    'The operation may or may not have landed — read the affected resource back before ' +
+    'retrying, and prefer a narrower invocation if this was a heavy call.'
+  )
+}
+
 class ToolExecutionTimeoutError extends Error {
   constructor(toolName: string, timeoutMs: number) {
     super(
@@ -880,7 +906,11 @@ async function executeToolAndReportInner(
       ...(terminalData !== undefined ? { data: terminalData } : {}),
     })
   } catch (error) {
-    const thrownMessage = toError(error).message
+    const thrownMessage = enrichOpaqueToolError(
+      toError(error).message,
+      toolCall.name,
+      toolCall.startTime
+    )
     const projection = inspectToolResultForCopilot(
       { success: false, error: thrownMessage },
       toolExecutionContext.resolvedSecretTraceRegistry,