diff --git a/apps/sim/background/schedule-execution.ts b/apps/sim/background/schedule-execution.ts
index 4c240e5f1e..0ee2b07f2f 100644
--- a/apps/sim/background/schedule-execution.ts
+++ b/apps/sim/background/schedule-execution.ts
@@ -1,3 +1,4 @@
+import { trace } from '@opentelemetry/api'
 import {
   db,
   jobExecutionLogs,
@@ -947,16 +948,28 @@ export async function executeScheduleJob(payload: ScheduleExecutionPayload) {
         )
       }
     } catch (error: unknown) {
-      if (isRetryableInfrastructureError(error)) {
-        await retryScheduleAfterInfraFailure({ payload, requestId, claimedAt, error })
-        return
-      }
+      try {
+        if (isRetryableInfrastructureError(error)) {
+          await retryScheduleAfterInfraFailure({ payload, requestId, claimedAt, error })
+          return
+        }
 
-      logger.error(`[${requestId}] Error processing schedule ${payload.scheduleId}`, error)
-      await releaseClaim(
-        now,
-        `Failed to release schedule ${payload.scheduleId} after unhandled error`
-      )
+        logger.error(`[${requestId}] Error processing schedule ${payload.scheduleId}`, error)
+        await releaseClaim(
+          now,
+          `Failed to release schedule ${payload.scheduleId} after unhandled error`
+        )
+      } catch (recoveryError: unknown) {
+        // A secondary failure during error recovery (e.g. a transient DB blip while
+        // releasing the claim or scheduling an infra retry) must not fault the run. The
+        // claim expires on its TTL and the next tick re-claims the schedule. Record the
+        // exception on the span so it stays visible in traces without faulting the run.
+        logger.error(
+          `[${requestId}] Failed to recover schedule ${payload.scheduleId} after error`,
+          recoveryError
+        )
+        trace.getActiveSpan()?.recordException(toError(recoveryError))
+      }
     }
   })
 }
diff --git a/apps/sim/background/webhook-execution.test.ts b/apps/sim/background/webhook-execution.test.ts
index 620c073ac0..7a75dc3e4f 100644
--- a/apps/sim/background/webhook-execution.test.ts
+++ b/apps/sim/background/webhook-execution.test.ts
@@ -2,17 +2,110 @@
  * @vitest-environment node
  */
 
+import {
+  dbChainMock,
+  dbChainMockFns,
+  executionPreprocessingMock,
+  executionPreprocessingMockFns,
+  loggingSessionMock,
+  loggingSessionMockFns,
+} from '@sim/testing'
 import { beforeEach, describe, expect, it, vi } from 'vitest'
 
-const { mockResolveWebhookRecordProviderConfig } = vi.hoisted(() => ({
+const {
+  mockResolveWebhookRecordProviderConfig,
+  mockExecuteWorkflowCore,
+  mockWasExecutionFinalizedByCore,
+  mockRecordException,
+  mockGetActiveSpan,
+} = vi.hoisted(() => ({
   mockResolveWebhookRecordProviderConfig: vi.fn(),
+  mockExecuteWorkflowCore: vi.fn(),
+  mockWasExecutionFinalizedByCore: vi.fn(),
+  mockRecordException: vi.fn(),
+  mockGetActiveSpan: vi.fn(),
 }))
 
+vi.mock('@opentelemetry/api', () => ({
+  trace: { getActiveSpan: mockGetActiveSpan },
+}))
+
+vi.mock('@sim/db', () => dbChainMock)
+vi.mock('@/lib/execution/preprocessing', () => executionPreprocessingMock)
+vi.mock('@/lib/logs/execution/logging-session', () => loggingSessionMock)
+
 vi.mock('@/lib/webhooks/env-resolver', () => ({
   resolveWebhookRecordProviderConfig: mockResolveWebhookRecordProviderConfig,
 }))
 
-import { resolveWebhookExecutionProviderConfig } from './webhook-execution'
+vi.mock('@/lib/workflows/executor/execution-core', () => ({
+  executeWorkflowCore: mockExecuteWorkflowCore,
+  wasExecutionFinalizedByCore: mockWasExecutionFinalizedByCore,
+}))
+
+vi.mock('@/lib/core/idempotency', () => ({
+  IdempotencyService: { createWebhookIdempotencyKey: vi.fn(() => 'idempotency-key') },
+  webhookIdempotency: {
+    executeWithIdempotency: vi.fn(
+      (_provider: string, _key: string, operation: () => Promise<unknown>) => operation()
+    ),
+  },
+}))
+
+vi.mock('@/lib/workflows/persistence/utils', () => ({
+  loadDeployedWorkflowState: vi.fn(async () => ({
+    blocks: {},
+    edges: [],
+    loops: {},
+    parallels: {},
+    deploymentVersionId: 'deployment-1',
+  })),
+}))
+
+vi.mock('@/lib/webhooks/providers', () => ({
+  getProviderHandler: vi.fn(() => ({})),
+}))
+
+vi.mock('@/lib/logs/execution/trace-spans/trace-spans', () => ({
+  buildTraceSpans: vi.fn(() => ({ traceSpans: [] })),
+}))
+
+vi.mock('@/lib/core/execution-limits', () => ({
+  createTimeoutAbortController: vi.fn(() => ({
+    signal: new AbortController().signal,
+    cleanup: vi.fn(),
+    isTimedOut: () => false,
+    timeoutMs: 120_000,
+  })),
+  getTimeoutErrorMessage: vi.fn(() => 'timed out'),
+}))
+
+vi.mock('@/lib/workflows/executor/pause-persistence', () => ({
+  handlePostExecutionPauseState: vi.fn(),
+}))
+
+vi.mock('@/lib/webhooks/attachment-processor', () => ({
+  WebhookAttachmentProcessor: class {},
+}))
+
+vi.mock('@/app/api/auth/oauth/utils', () => ({
+  resolveOAuthAccountId: vi.fn(),
+}))
+
+vi.mock('@/executor/execution/snapshot', () => ({
+  ExecutionSnapshot: class {},
+}))
+
+vi.mock('@/tools/safe-assign', () => ({ safeAssign: vi.fn() }))
+
+vi.mock('@/blocks', () => ({ getBlock: vi.fn(() => null) }))
+
+vi.mock('@/triggers', () => ({
+  getTrigger: vi.fn(),
+  isTriggerValid: vi.fn(() => false),
+}))
+
+import { executeWebhookJob, resolveWebhookExecutionProviderConfig } from './webhook-execution'
 
 describe('resolveWebhookExecutionProviderConfig', () => {
   beforeEach(() => {
@@ -66,3 +159,64 @@ describe('resolveWebhookExecutionProviderConfig', () => {
     )
   })
 })
+
+describe('executeWebhookJob fault vs error handling', () => {
+  const payload = {
+    webhookId: 'webhook-1',
+    workflowId: 'workflow-1',
+    userId: 'user-1',
+    executionId: 'execution-1',
+    requestId: 'request-1',
+    provider: 'gmail',
+    body: { message: 'hello' },
+    headers: {},
+    path: '/webhook',
+    workspaceId: 'workspace-1',
+  }
+
+  beforeEach(() => {
+    vi.clearAllMocks()
+    executionPreprocessingMockFns.mockPreprocessExecution.mockResolvedValue({
+      success: true,
+      workflowRecord: { workspaceId: 'workspace-1', userId: 'user-1', variables: {} },
+      executionTimeout: { async: 120_000 },
+    })
+    mockResolveWebhookRecordProviderConfig.mockImplementation(async (record) => record)
+    dbChainMockFns.limit.mockResolvedValue([{ id: 'webhook-1' }])
+    mockGetActiveSpan.mockReturnValue({ recordException: mockRecordException })
+  })
+
+  it('completes the run (does not throw) when the failure was finalized by core', async () => {
+    mockExecuteWorkflowCore.mockRejectedValue(
+      new Error('Gmail 2 is missing required fields: Label')
+    )
+    mockWasExecutionFinalizedByCore.mockReturnValue(true)
+
+    const result = await executeWebhookJob(payload)
+
+    expect(result).toMatchObject({
+      success: false,
+      workflowId: 'workflow-1',
+      executionId: 'execution-1',
+      provider: 'gmail',
+    })
+    expect(loggingSessionMockFns.mockWaitForPostExecution).toHaveBeenCalled()
+    // User/workflow errors are already recorded by core — the catch must not re-log them.
+    expect(loggingSessionMockFns.mockSafeCompleteWithError).not.toHaveBeenCalled()
+    // The error is still recorded on the run span so it stays visible in traces.
+    expect(mockRecordException).toHaveBeenCalledWith(
+      expect.objectContaining({ message: 'Gmail 2 is missing required fields: Label' })
+    )
+  })
+
+  it('faults the run (re-throws) when the failure was not finalized by core', async () => {
+    mockExecuteWorkflowCore.mockRejectedValue(new Error('Workflow state not found'))
+    mockWasExecutionFinalizedByCore.mockReturnValue(false)
+
+    await expect(executeWebhookJob(payload)).rejects.toThrow('Workflow state not found')
+    // waitForPostExecution must run on every path so the finalized-by-core signal is always reliable.
+    expect(loggingSessionMockFns.mockWaitForPostExecution).toHaveBeenCalled()
+    // Pipeline/infra errors are recorded here before re-throwing to fault the trigger.dev run.
+    expect(loggingSessionMockFns.mockSafeCompleteWithError).toHaveBeenCalled()
+  })
+})
diff --git a/apps/sim/background/webhook-execution.ts b/apps/sim/background/webhook-execution.ts
index 1753813d84..41048f9208 100644
--- a/apps/sim/background/webhook-execution.ts
+++ b/apps/sim/background/webhook-execution.ts
@@ -1,3 +1,4 @@
+import { trace } from '@opentelemetry/api'
 import { db } from '@sim/db'
 import { account, webhook } from '@sim/db/schema'
 import { createLogger, runWithRequestContext } from '@sim/logger'
@@ -616,8 +617,27 @@ async function executeWebhookJobInternal(
       provider: payload.provider,
     })
 
+    // The finalized flag is set inside a fire-and-forget post-execution promise; await it so the
+    // signal is reliable and the failure is fully persisted before we decide fault vs error.
+    await loggingSession.waitForPostExecution()
+
+    // A failure inside workflow execution (block error, provider 4xx, missing required field, etc.)
+    // is finalized by core and already recorded in the execution logs. That is a user/workflow error,
+    // not a trigger.dev job fault — complete the run normally so we don't fire a false alert. Errors
+    // that were not finalized came from the webhook pipeline itself, so we re-throw to fault below.
     if (wasExecutionFinalizedByCore(error, executionId)) {
-      throw error
+      // Record the exception on the run span so it stays visible in traces without
+      // marking the span as ERROR — that status is what faults the trigger.dev run.
+      trace.getActiveSpan()?.recordException(toError(error))
+
+      return {
+        success: false,
+        workflowId: payload.workflowId,
+        executionId,
+        output: hasExecutionResult(error) ? error.executionResult.output : {},
+        executedAt: new Date().toISOString(),
+        provider: payload.provider,
+      }
     }
 
     try {