fix(providers): retry transient failures on OpenAI Responses and Gemini

apps/sim/lib/core/errors/provider-quota.ts

@@ -0,0 +1,19 @@
+/**
+ * True when a provider rejection body reports an exhausted balance rather than a rate
+ * limit. OpenAI returns 429 for both, but only a rate limit reopens: a spent account
+ * stands until someone adds credit, so retrying it cannot succeed.
+ */
+export function isQuotaExhaustionBody(errorText: string): boolean {
+  try {
+    const body = JSON.parse(errorText) as { error?: { type?: string; code?: string } }
+    const type = body.error?.type
+    const code = body.error?.code
+    return (
+      type === 'insufficient_quota' ||
+      code === 'insufficient_quota' ||
+      code === 'credit_balance_exhausted'
+    )
+  } catch {
+    return false
+  }
+}

apps/sim/lib/core/errors/retryable-infrastructure.ts

@@ -97,6 +97,19 @@ export function isRetryableInfrastructureError(error: unknown): boolean {
   return Boolean(describeRetryableInfrastructureError(error))
 }
 
+/**
+ * A network-level failure only — a dropped, refused, or timed-out socket anywhere in the
+ * cause chain. Narrower than {@link isRetryableInfrastructureError}: database and application
+ * codes are excluded, so a caller replaying a billed request never mistakes one for a socket.
+ */
+export function isRetryableNetworkError(error: unknown): boolean {
+  return getErrorChain(error).some(
+    (candidate) =>
+      (typeof candidate.code === 'string' && RETRYABLE_NETWORK_ERROR_CODES.has(candidate.code)) ||
+      (typeof candidate.errno === 'string' && RETRYABLE_NETWORK_ERROR_CODES.has(candidate.errno))
+  )
+}
+
 /**
  * A retryable infrastructure failure raised strictly BEFORE the guarded
  * operation performed any effect (no workflow block ran, no mutation

apps/sim/lib/embeddings/client.ts

@@ -11,6 +11,7 @@ import {
   wireFallback,
 } from '@/lib/core/config/env-capabilities'
 import { isHosted } from '@/lib/core/config/env-flags'
+import { isQuotaExhaustionBody } from '@/lib/core/errors/provider-quota'
 import {
   ProviderQuotaExhaustedError,
   recordProviderCooldown,
@@ -254,26 +255,6 @@ export function isBYOKEmbeddingCredentialRejection(error: unknown): error is Emb
   )
 }
 
-/**
- * True when a rejection body reports an exhausted balance rather than a rate
- * limit. OpenAI returns 429 for both, but only a rate limit reopens: a spent
- * account stands until someone adds credit, so retrying it cannot succeed.
- */
-function isQuotaExhaustionBody(errorText: string): boolean {
-  try {
-    const body = JSON.parse(errorText) as { error?: { type?: string; code?: string } }
-    const type = body.error?.type
-    const code = body.error?.code
-    return (
-      type === 'insufficient_quota' ||
-      code === 'insufficient_quota' ||
-      code === 'credit_balance_exhausted'
-    )
-  } catch {
-    return false
-  }
-}
-
 /** Reads a bounded provider body for internal diagnostics and quota classification. */
 async function readEmbeddingErrorBody(response: Response, signal?: AbortSignal): Promise<string> {
   try {

apps/sim/providers/anthropic/index.ts

@@ -4,6 +4,7 @@ import type { StreamingExecution } from '@/executor/types'
 import { executeAnthropicProviderRequest } from '@/providers/anthropic/core'
 import { getCachedProviderClient } from '@/providers/client-cache'
 import { getProviderDefaultModel, getProviderModels } from '@/providers/models'
+import { PROVIDER_MAX_RETRIES } from '@/providers/transport'
 import type { ProviderConfig, ProviderRequest, ProviderResponse } from '@/providers/types'
 
 const logger = createLogger('AnthropicProvider')
@@ -24,7 +25,10 @@ export const anthropicProvider: ProviderConfig = {
       providerLabel: 'Anthropic',
       createClient: (apiKey) => {
         const cacheKey = `anthropic::${apiKey}`
-        return getCachedProviderClient(cacheKey, () => new Anthropic({ apiKey }))
+        return getCachedProviderClient(
+          cacheKey,
+          () => new Anthropic({ apiKey, maxRetries: PROVIDER_MAX_RETRIES })
+        )
       },
       logger,
     })

apps/sim/providers/azure-anthropic/index.ts

@@ -6,6 +6,7 @@ import type { StreamingExecution } from '@/executor/types'
 import { executeAnthropicProviderRequest } from '@/providers/anthropic/core'
 import { getCachedProviderClient } from '@/providers/client-cache'
 import { getProviderDefaultModel, getProviderModels } from '@/providers/models'
+import { PROVIDER_MAX_RETRIES } from '@/providers/transport'
 import type { ProviderConfig, ProviderRequest, ProviderResponse } from '@/providers/types'
 
 const logger = createLogger('AzureAnthropicProvider')
@@ -79,6 +80,7 @@ export const azureAnthropicProvider: ProviderConfig = {
             new Anthropic({
               baseURL,
               apiKey,
+              maxRetries: PROVIDER_MAX_RETRIES,
               ...(pinnedFetch ? { fetch: pinnedFetch } : {}),
               defaultHeaders: {
                 'anthropic-version': anthropicVersion,

apps/sim/providers/azure-openai/index.ts

@@ -48,6 +48,7 @@ import { createStreamingExecution } from '@/providers/streaming-execution'
 import { isAbortError, parseToolArguments } from '@/providers/streaming-tool-loop-shared'
 import { adaptOpenAIChatToolSchema } from '@/providers/tool-schema-adapter'
 import { enrichLastModelSegmentFromChatCompletions } from '@/providers/trace-enrichment'
+import { openAICompatTransport } from '@/providers/transport'
 import type {
   FunctionCallResponse,
   ProviderConfig,
@@ -97,6 +98,7 @@ async function executeChatCompletionsRequest(
     apiKey: request.apiKey!,
     apiVersion: azureApiVersion,
     endpoint: azureEndpoint,
+    ...openAICompatTransport(),
     ...(pinnedFetch ? { fetch: pinnedFetch } : {}),
   })
 

apps/sim/providers/conversation-generation-coverage.test.ts

@@ -21,13 +21,55 @@ function insideNamedAncestor(node: ts.Node, name: string): boolean {
 }
 
 function preparedPayload(node: ts.Node): boolean {
+  if (ts.isIdentifier(node)) return preparedBinding(node)
   return (
     ts.isAwaitExpression(node) &&
     ts.isCallExpression(node.expression) &&
     node.expression.expression.getText() === 'prepareConversationGeneration'
   )
 }
 
+/**
+ * Whether the nearest declaration of `identifier` is a `const` bound to a prepared payload.
+ * Retried sends prepare once and replay the binding, since preparing can itself call a model
+ * to compact history. The nearest declaration decides, so an inner shadow must be prepared too.
+ */
+function preparedBinding(identifier: ts.Identifier): boolean {
+  const declares = (name: ts.BindingName): boolean =>
+    ts.isIdentifier(name)
+      ? name.text === identifier.text
+      : name.elements.some((element) => !ts.isOmittedExpression(element) && declares(element.name))
+  for (let scope = identifier.parent; scope; scope = scope.parent) {
+    if (ts.isFunctionLike(scope) && scope.parameters.some((parameter) => declares(parameter.name)))
+      return false
+    if (
+      ts.isCatchClause(scope) &&
+      scope.variableDeclaration &&
+      declares(scope.variableDeclaration.name)
+    )
+      return false
+    if (
+      (ts.isForStatement(scope) || ts.isForInStatement(scope) || ts.isForOfStatement(scope)) &&
+      scope.initializer &&
+      ts.isVariableDeclarationList(scope.initializer) &&
+      scope.initializer.declarations.some((declaration) => declares(declaration.name))
+    )
+      return false
+    if (!ts.isBlock(scope) && !ts.isSourceFile(scope)) continue
+    for (const statement of scope.statements) {
+      if (!ts.isVariableStatement(statement)) continue
+      const declaration = statement.declarationList.declarations.find((d) => declares(d.name))
+      if (!declaration) continue
+      return (
+        Boolean(statement.declarationList.flags & ts.NodeFlags.Const) &&
+        declaration.initializer !== undefined &&
+        preparedPayload(declaration.initializer)
+      )
+    }
+  }
+  return false
+}
+
 describe('provider generation context coverage', () => {
   it('guards every model SDK send, shared stream callback, retry and finalizer', () => {
     const uncovered: string[] = []
@@ -60,7 +102,7 @@ describe('provider generation context coverage', () => {
             file.endsWith('/openai-compat/streaming-tool-loop.ts')
           ) {
             argument = 0
-          } else if (callee === 'JSON.stringify' && insideNamedAncestor(node, 'postOnce')) {
+          } else if (callee === 'JSON.stringify' && insideNamedAncestor(node, 'post')) {
             argument = 0
           }
           if (argument !== undefined) {

apps/sim/providers/gemini/core.test.ts

@@ -1,4 +1,8 @@
-import type { GenerateContentParameters, GenerateContentResponse } from '@google/genai'
+import {
+  ApiError,
+  type GenerateContentParameters,
+  type GenerateContentResponse,
+} from '@google/genai'
 import { providersMock } from '@sim/testing/mocks/providers.mock'
 import {
   providersConversationHistoryMock,
@@ -142,6 +146,25 @@ describe('Vertex Gemini request compatibility', () => {
     }
   )
 
+  /** The SDK's own retry is off (it would replace every error message), so ours must run. */
+  it('replays a transient server error before reporting it', async () => {
+    vi.useFakeTimers()
+    try {
+      const generateContent = vi
+        .fn()
+        .mockRejectedValueOnce(new ApiError({ message: 'Internal error', status: 500 }))
+        .mockResolvedValue(textTurn())
+
+      const pending = run('vertex/gemini-3.8-flash', generateContent)
+      await vi.runAllTimersAsync()
+
+      await expect(pending).resolves.toMatchObject({ content: 'answer' })
+      expect(generateContent).toHaveBeenCalledTimes(2)
+    } finally {
+      vi.useRealTimers()
+    }
+  })
+
   it('prices Vertex-only catalog entries using the namespaced model ID', async () => {
     const generateContent = vi.fn().mockResolvedValue(textTurn())
     const result = await run('vertex/gemini-3.8-flash', generateContent)

apps/sim/providers/gemini/core.ts

@@ -32,11 +32,13 @@ import {
   ensureStructResponse,
   extractAllFunctionCallParts,
   extractTextContent,
+  geminiRetryDelayMs,
   mapToThinkingBudget,
   mapToThinkingLevel,
   supportsDisablingGemini25Thinking,
 } from '@/providers/google/utils'
 import { getModelCapabilities, isKnownModelId } from '@/providers/models'
+import { withProviderRetry } from '@/providers/retry'
 import { executeProviderTool } from '@/providers/runtime-context'
 import { createSettledAgentEventStream } from '@/providers/stream-events'
 import { createStreamingExecution } from '@/providers/streaming-execution'
@@ -962,6 +964,12 @@ export async function executeGeminiRequest(
   }
 
   const logger = createLogger(providerType === 'google' ? 'GoogleProvider' : 'VertexProvider')
+  const retryOptions = {
+    logger,
+    label: providerType === 'google' ? 'Gemini' : 'Vertex AI',
+    abortSignal: request.abortSignal,
+    retryAfterMs: geminiRetryDelayMs,
+  }
 
   logger.info(`Preparing ${providerType} Gemini request`, {
     model,
@@ -1148,12 +1156,14 @@ export async function executeGeminiRequest(
     if (shouldStream) {
       logger.info('Handling Gemini streaming response')
 
-      const streamGenerator = await ai.models.generateContentStream(
-        await prepareConversationGeneration(request, 'gemini', {
-          model,
-          contents,
-          config: geminiConfig,
-        })
+      const streamPayload = await prepareConversationGeneration(request, 'gemini', {
+        model,
+        contents,
+        config: geminiConfig,
+      })
+      const streamGenerator = await withProviderRetry(
+        () => ai.models.generateContentStream(streamPayload),
+        retryOptions
       )
       const firstResponseTime = Date.now() - initialCallTime
 
@@ -1202,12 +1212,14 @@ export async function executeGeminiRequest(
     }
 
     // Non-streaming request
-    const response = await ai.models.generateContent(
-      await prepareConversationGeneration(request, 'gemini', {
-        model,
-        contents,
-        config: geminiConfig,
-      })
+    const responsePayload = await prepareConversationGeneration(request, 'gemini', {
+      model,
+      contents,
+      config: geminiConfig,
+    })
+    const response = await withProviderRetry(
+      () => ai.models.generateContent(responsePayload),
+      retryOptions
     )
     if (!extractAllFunctionCallParts(response.candidates?.[0]).length) {
       await captureProviderConversationStep(
@@ -1256,12 +1268,14 @@ export async function executeGeminiRequest(
       }
 
       const finalStartTime = Date.now()
-      const finalResponse = await ai.models.generateContent(
-        await prepareConversationGeneration(request, 'gemini', {
-          model,
-          contents: currentState.contents,
-          config: finalConfig,
-        })
+      const finalResponsePayload = await prepareConversationGeneration(request, 'gemini', {
+        model,
+        contents: currentState.contents,
+        config: finalConfig,
+      })
+      const finalResponse = await withProviderRetry(
+        () => ai.models.generateContent(finalResponsePayload),
+        retryOptions
       )
       if (!extractAllFunctionCallParts(finalResponse.candidates?.[0]).length) {
         await captureProviderConversationStep(
@@ -1375,12 +1389,14 @@ export async function executeGeminiRequest(
 
         /** Resolve the final turn, then project its settled answer when streaming was requested. */
         const nextModelStartTime = Date.now()
-        const nextResponse = await ai.models.generateContent(
-          await prepareConversationGeneration(request, 'gemini', {
-            model,
-            contents: state.contents,
-            config: nextConfig,
-          })
+        const nextResponsePayload = await prepareConversationGeneration(request, 'gemini', {
+          model,
+          contents: state.contents,
+          config: nextConfig,
+        })
+        const nextResponse = await withProviderRetry(
+          () => ai.models.generateContent(nextResponsePayload),
+          retryOptions
         )
         if (!extractAllFunctionCallParts(nextResponse.candidates?.[0]).length) {
           await captureProviderConversationStep(

apps/sim/providers/gemini/streaming-tool-loop.ts

@@ -37,7 +37,9 @@ import {
   cleanSchemaForGemini,
   convertUsageMetadata,
   ensureStructResponse,
+  geminiRetryDelayMs,
 } from '@/providers/google/utils'
+import { withProviderRetry } from '@/providers/retry'
 import { executeProviderTool } from '@/providers/runtime-context'
 import type { AgentStreamEvent, ToolCallEndStatus } from '@/providers/stream-events'
 import {
@@ -309,15 +311,22 @@ export function createGeminiStreamingToolLoopStream(
                 )
 
             const modelStart = Date.now()
-            const streamGenerator = await ai.models.generateContentStream(
-              await prepareConversationGeneration(request, 'gemini', {
-                model,
-                contents,
-                config: {
-                  ...turnConfig,
-                  abortSignal: loopAbortController.signal,
-                },
-              })
+            const turnPayload = await prepareConversationGeneration(request, 'gemini', {
+              model,
+              contents,
+              config: {
+                ...turnConfig,
+                abortSignal: loopAbortController.signal,
+              },
+            })
+            const streamGenerator = await withProviderRetry(
+              () => ai.models.generateContentStream(turnPayload),
+              {
+                logger,
+                label: 'Gemini',
+                abortSignal: loopAbortController.signal,
+                retryAfterMs: geminiRetryDelayMs,
+              }
             )
 
             const drained = await drainGeminiTurn(