fix(providers): name the failing phase of a stalled OpenAI call, and reject a failed generation

.claude/rules/sim-ui-copy.md

@@ -0,0 +1,46 @@
+---
+paths:
+  - "apps/sim/**/*.tsx"
+  - "apps/sim/components/emcn/**"
+---
+
+# UI Copy
+
+**Do not add subtitles, helper text, or descriptive copy beneath headings, labels, cards, or settings by default.** Prefer one concise, self-explanatory heading or label. Only add supporting copy when the user explicitly asks for it, or when it is necessary to prevent misunderstanding or error — and never use it to restate the heading.
+
+This applies to product surfaces: settings rows, modals, panels, cards, list rows, empty states, form fields, and section headers. Marketing surfaces (`app/(landing)`, docs) are governed by `constitution.md` instead.
+
+**Carve-out — settings section metadata.** `SettingsNavigationItem.description` in `components/settings/navigation.ts` stays required, and `SettingsPanel` keeps rendering it as the page subtitle. Settings sections are reached through a nav list where the description is the only thing distinguishing adjacent sections, so it earns its place by the "prevents misunderstanding" test. Keep those descriptions verb-first and one line, per `sim-settings-pages.md`. Everything else on a settings page — inline `<p>` blurbs under section headings, field hints, modal bodies, row subtitles — follows the default rule above.
+
+## The default is no description
+
+```tsx
+// ✗ Bad — the subtitle restates the heading
+<h3>API Keys</h3>
+<p className='text-[var(--text-muted)] text-caption'>Manage your API keys.</p>
+
+// ✗ Bad — decorative filler under a field label
+<ChipModalField title='Workspace name' hint='The name of your workspace.' />
+
+// ✓ Good — the label carries the whole meaning
+<h3>API Keys</h3>
+<ChipModalField title='Workspace name' />
+```
+
+If a heading needs a subtitle to be understood, the heading is wrong. Fix the heading — don't append a second line.
+
+## When supporting copy earns its place
+
+Keep (or add) a description only when it carries information the label cannot, and its absence would cause a mistake:
+
+- **Irreversible or destructive consequences** — "Deleting this workspace removes every workflow and log. This cannot be undone."
+- **A non-obvious format, unit, or bound** — "Comma-separated. Max 50 domains.", "Cost per 1M input tokens."
+- **A security or access implication** — "This key is shown once and grants full workspace access."
+- **A state the user cannot otherwise see** — "Inherited from your organization's policy."
+- **Instructional copy that advances a flow** — "We sent a 6-digit code to you@example.com."
+
+Everything else — restatements, "Manage your X", "Configure your Y", feature blurbs, encouragement — gets deleted.
+
+## Component APIs
+
+Description/hint slots on shared components are **optional**, never required, and must reserve no layout space when omitted. A component that forces every consumer to supply a subtitle forces every consumer to violate this rule. When adding a new shared component, ship it without a description slot and add one only once a real caller meets the bar above.

.cursor/rules/sim-ui-copy.mdc

@@ -0,0 +1,44 @@
+---
+description: UI copy conventions — no default subtitles or helper text under headings, labels, cards, or settings
+globs: ["apps/sim/**/*.tsx"]
+---
+# UI Copy
+
+**Do not add subtitles, helper text, or descriptive copy beneath headings, labels, cards, or settings by default.** Prefer one concise, self-explanatory heading or label. Only add supporting copy when the user explicitly asks for it, or when it is necessary to prevent misunderstanding or error — and never use it to restate the heading.
+
+This applies to product surfaces: settings rows, modals, panels, cards, list rows, empty states, form fields, and section headers. Marketing surfaces (`app/(landing)`, docs) are governed by `constitution.mdc` instead.
+
+**Carve-out — settings section metadata.** `SettingsNavigationItem.description` in `components/settings/navigation.ts` stays required, and `SettingsPanel` keeps rendering it as the page subtitle. Settings sections are reached through a nav list where the description is the only thing distinguishing adjacent sections. Everything else on a settings page — inline `<p>` blurbs under section headings, field hints, modal bodies, row subtitles — follows the default rule above.
+
+## The default is no description
+
+```tsx
+// ✗ Bad — the subtitle restates the heading
+<h3>API Keys</h3>
+<p className='text-[var(--text-muted)] text-caption'>Manage your API keys.</p>
+
+// ✗ Bad — decorative filler under a field label
+<ChipModalField title='Workspace name' hint='The name of your workspace.' />
+
+// ✓ Good — the label carries the whole meaning
+<h3>API Keys</h3>
+<ChipModalField title='Workspace name' />
+```
+
+If a heading needs a subtitle to be understood, the heading is wrong. Fix the heading — don't append a second line.
+
+## When supporting copy earns its place
+
+Keep (or add) a description only when it carries information the label cannot, and its absence would cause a mistake:
+
+- **Irreversible or destructive consequences** — "Deleting this workspace removes every workflow and log. This cannot be undone."
+- **A non-obvious format, unit, or bound** — "Comma-separated. Max 50 domains.", "Cost per 1M input tokens."
+- **A security or access implication** — "This key is shown once and grants full workspace access."
+- **A state the user cannot otherwise see** — "Inherited from your organization's policy."
+- **Instructional copy that advances a flow** — "We sent a 6-digit code to you@example.com."
+
+Everything else — restatements, "Manage your X", "Configure your Y", feature blurbs, encouragement — gets deleted.
+
+## Component APIs
+
+Description/hint slots on shared components are **optional**, never required, and must reserve no layout space when omitted. A component that forces every consumer to supply a subtitle forces every consumer to violate this rule. When adding a new shared component, ship it without a description slot and add one only once a real caller meets the bar above.

apps/sim/executor/handlers/agent/agent-handler.test.ts

@@ -979,6 +979,49 @@ describe('AgentBlockHandler', () => {
       )
     })
 
+    /**
+     * A stalled model call reaches here as the runtime's own `TimeoutError`, whose bare
+     * message ("The operation timed out.") names nothing. It must become a Sim-level
+     * message WITHOUT discarding the phase detail the provider attached — that detail is
+     * the only thing distinguishing "never answered" from "body never completed".
+     */
+    it('maps a provider TimeoutError to a Sim message while keeping the phase detail', async () => {
+      const inputs = { model: 'gpt-4o', userPrompt: 'hi', apiKey: 'test-api-key' }
+      mockGetProviderFromModel.mockReturnValue('openai')
+
+      // Faithful to production: providers rewrap the transport failure in a
+      // ProviderError, which overwrites `name` — so only the cause still classifies it.
+      const transport = new Error(
+        'The operation timed out. [phase=reading-response-body elapsedMs=60001 status=200 contentLength=32116]'
+      )
+      transport.name = 'TimeoutError'
+      const wrapped = new Error(transport.message, { cause: transport })
+      wrapped.name = 'ProviderError'
+      mockExecuteProviderRequest.mockRejectedValueOnce(wrapped)
+
+      const error = await handler.execute(mockContext, mockBlock, inputs).catch((e) => e)
+
+      expect(error.message).toContain('Provider request timed out')
+      expect(error.message).toContain('phase=reading-response-body')
+      expect(error.message).toContain('status=200')
+    })
+
+    it('maps a provider AbortError the same way', async () => {
+      const inputs = { model: 'gpt-4o', userPrompt: 'hi', apiKey: 'test-api-key' }
+      mockGetProviderFromModel.mockReturnValue('openai')
+
+      const aborted = new Error('aborted [phase=awaiting-response-headers elapsedMs=12]')
+      aborted.name = 'AbortError'
+      const wrapped = new Error(aborted.message, { cause: aborted })
+      wrapped.name = 'ProviderError'
+      mockExecuteProviderRequest.mockRejectedValueOnce(wrapped)
+
+      const error = await handler.execute(mockContext, mockBlock, inputs).catch((e) => e)
+
+      expect(error.message).toContain('Provider request timed out')
+      expect(error.message).toContain('phase=awaiting-response-headers')
+    })
+
     it('should handle streaming responses with text/event-stream content type', async () => {
       const mockStreamBody = new ReadableStream({
         start(controller) {

apps/sim/executor/handlers/agent/agent-handler.ts

@@ -71,6 +71,22 @@ import { getToolAsync } from '@/tools/utils.server'
 
 const logger = createLogger('AgentBlockHandler')
 
+/**
+ * True when a failure originated from a transport deadline or abort, at any depth of the
+ * cause chain.
+ *
+ * Providers rewrap transport failures (`ProviderError` overwrites `name`), so a check on
+ * the top-level `name` alone misses every wrapped case. Bounded to a short walk so a
+ * self-referential cause cannot loop.
+ */
+function isTransportTimeout(error: unknown): boolean {
+  for (let current = error, depth = 0; current instanceof Error && depth < 5; depth++) {
+    if (current.name === 'AbortError' || current.name === 'TimeoutError') return true
+    current = current.cause
+  }
+  return false
+}
+
 /**
  * Handler for Agent blocks that process LLM requests with optional tools.
  */
@@ -1299,8 +1315,15 @@ export class AgentBlockHandler implements BlockHandler {
       timestamp: new Date().toISOString(),
     })
 
-    if (error.name === 'AbortError') {
-      throw new Error('Provider request timed out - the API took too long to respond')
+    /**
+     * The original message is appended rather than replaced: providers annotate it with
+     * the request phase they died in, which is the only thing separating a request that
+     * was never answered from one whose body stalled.
+     */
+    if (isTransportTimeout(error)) {
+      throw new Error(
+        `Provider request timed out - the API took too long to respond (${error.message})`
+      )
     }
     if (error.name === 'TypeError' && error.message.includes('fetch')) {
       throw new Error(