diff --git a/apps/sim/background/cleanup-logs-files.test.ts b/apps/sim/background/cleanup-logs-files.test.ts
new file mode 100644
index 00000000000..ebcb62fbc23
--- /dev/null
+++ b/apps/sim/background/cleanup-logs-files.test.ts
@@ -0,0 +1,111 @@
+/**
+ * @vitest-environment node
+ */
+
+import { dbChainMockFns, resetDbChainMock, schemaMock } from '@sim/testing'
+import { beforeEach, describe, expect, it, vi } from 'vitest'
+
+const { mockDeleteFiles, mockDeleteFileMetadata } = vi.hoisted(() => ({
+  mockDeleteFiles: vi.fn(),
+  mockDeleteFileMetadata: vi.fn(),
+}))
+
+vi.mock('@trigger.dev/sdk', () => ({
+  task: vi.fn((config) => config),
+  queue: vi.fn((config) => config),
+}))
+vi.mock('@/lib/billing/cleanup-dispatcher', () => ({ runCleanupWithLimits: vi.fn() }))
+vi.mock('@/lib/execution/payloads/large-value-metadata', () => ({
+  LIVE_PAUSED_REFERENCE_STATUSES: ['paused', 'partially_resumed', 'cancelling'],
+  markLargeValuesDeleted: vi.fn(),
+  pruneLargeValueMetadata: vi.fn(async () => ({
+    referencesDeleted: 0,
+    dependenciesDeleted: 0,
+    tombstonesDeleted: 0,
+  })),
+  unreferencedLargeValuePredicate: vi.fn(),
+}))
+vi.mock('@/lib/logs/execution/snapshot/service', () => ({
+  snapshotService: { cleanupOrphanedSnapshots: vi.fn() },
+}))
+vi.mock('@/lib/uploads', () => ({
+  isUsingCloudStorage: vi.fn(() => true),
+  StorageService: { deleteFiles: mockDeleteFiles },
+}))
+vi.mock('@/lib/uploads/server/metadata', () => ({
+  deleteFileMetadata: mockDeleteFileMetadata,
+}))
+
+import { createCleanupBudgets } from '@/lib/cleanup/limits'
+import { runCleanupLogs } from '@/background/cleanup-logs'
+
+const payload = {
+  label: 'free/1',
+  plan: 'free' as const,
+  retentionHours: 720,
+  workspaceIds: ['workspace-1'],
+}
+const rows = [
+  { id: 'log-1', files: [{ key: 'file-a' }, { key: 'file-b' }] },
+  { id: 'log-2', files: [{ key: 'file-c' }] },
+]
+
+describe('bounded log cleanup file failures', () => {
+  beforeEach(() => {
+    vi.clearAllMocks()
+    resetDbChainMock()
+    dbChainMockFns.limit.mockResolvedValueOnce(rows)
+    dbChainMockFns.returning.mockResolvedValueOnce(rows.map(({ id }) => ({ id })))
+    mockDeleteFiles.mockImplementation(async (keys: string[]) => ({
+      deleted: keys.length,
+      failed: [],
+    }))
+    mockDeleteFileMetadata.mockResolvedValue(true)
+  })
+
+  it.each([
+    {
+      name: 'the storage request throws',
+      fail: () => mockDeleteFiles.mockRejectedValueOnce(new Error('storage unavailable')),
+    },
+    {
+      name: 'storage returns a partial failure',
+      fail: () =>
+        mockDeleteFiles.mockResolvedValueOnce({
+          deleted: 1,
+          failed: [{ key: 'file-b', error: 'storage unavailable' }],
+        }),
+    },
+    {
+      name: 'metadata deletion throws',
+      fail: () => mockDeleteFileMetadata.mockRejectedValueOnce(new Error('database unavailable')),
+    },
+  ])('keeps the entire log batch retryable when $name', async ({ fail }) => {
+    fail()
+    const budgets = createCleanupBudgets({ workflowLogs: 2 })
+
+    await expect(runCleanupLogs(payload, budgets)).rejects.toThrow('Log file cleanup failed')
+
+    expect(dbChainMockFns.delete).not.toHaveBeenCalled()
+    expect(mockDeleteFiles).toHaveBeenCalledTimes(1)
+    expect(budgets.workflowLogs.remaining).toBe(0)
+
+    dbChainMockFns.limit.mockResolvedValueOnce(rows)
+    await runCleanupLogs(payload, createCleanupBudgets({ workflowLogs: 2 }))
+
+    expect(mockDeleteFiles).toHaveBeenNthCalledWith(2, ['file-a', 'file-b'], 'execution')
+    expect(mockDeleteFiles).toHaveBeenNthCalledWith(3, ['file-c'], 'execution')
+    expect(dbChainMockFns.delete).toHaveBeenCalledExactlyOnceWith(schemaMock.workflowExecutionLogs)
+  })
+
+  it('deletes log rows only after every file and its metadata succeeds', async () => {
+    await runCleanupLogs(payload, createCleanupBudgets({ workflowLogs: 2 }))
+
+    expect(mockDeleteFiles).toHaveBeenCalledTimes(2)
+    expect(mockDeleteFileMetadata).toHaveBeenCalledTimes(3)
+    expect(dbChainMockFns.delete).toHaveBeenCalledExactlyOnceWith(schemaMock.workflowExecutionLogs)
+    const deleteOrder = dbChainMockFns.delete.mock.invocationCallOrder[0]
+    expect(mockDeleteFiles.mock.invocationCallOrder.at(-1)).toBeLessThan(deleteOrder)
+    expect(mockDeleteFileMetadata.mock.invocationCallOrder.at(-1)).toBeLessThan(deleteOrder)
+  })
+})
diff --git a/apps/sim/background/cleanup-logs.ts b/apps/sim/background/cleanup-logs.ts
index e46127a8e6a..c26b2f2a76d 100644
--- a/apps/sim/background/cleanup-logs.ts
+++ b/apps/sim/background/cleanup-logs.ts
@@ -429,6 +429,7 @@ async function cleanupWorkflowExecutionLogs(
     onBatch: async (rows) => {
       for (const row of rows) {
         await deleteExecutionFiles(row.files, fileStats)
+        if (budget && fileStats.filesDeleteFailed) throw new Error('Log file cleanup failed')
       }
     },
     batchSize: WORKFLOW_LOG_CLEANUP_BATCH_SIZE,
@@ -486,7 +487,6 @@ export async function runCleanupLogs(
   logger.info(
     `[${label}] workflow_execution_logs files: ${workflowResults.filesDeleted}/${workflowResults.filesTotal} deleted, ${workflowResults.filesDeleteFailed} failed`
   )
-  if (budgets && workflowResults.filesDeleteFailed) throw new Error('Log file cleanup failed')
   const largeValueResults = await cleanupLargeExecutionValues(
     workspaceIds,
     retentionDate,