diff --git a/apps/sim/background/schedule-execution.ts b/apps/sim/background/schedule-execution.ts
index 4c6b1a9cba8..a786cefd14e 100644
--- a/apps/sim/background/schedule-execution.ts
+++ b/apps/sim/background/schedule-execution.ts
@@ -7,7 +7,7 @@ import {
   workflowSchedule,
 } from '@sim/db'
 import { createLogger, runWithRequestContext } from '@sim/logger'
-import { toError } from '@sim/utils/errors'
+import { describeError, toError } from '@sim/utils/errors'
 import { generateId } from '@sim/utils/id'
 import { backoffWithJitter } from '@sim/utils/retry'
 import { task } from '@trigger.dev/sdk'
@@ -156,7 +156,7 @@ async function applyScheduleUpdate(
 
     return updatedRows.length > 0
   } catch (error) {
-    logger.error(`[${requestId}] ${context}`, error)
+    logger.error(`[${requestId}] ${context}`, error, { cause: describeError(error) })
     throw error
   }
 }
@@ -530,7 +530,13 @@ async function runWorkflowExecution({
       }
     }
 
-    logger.error(`[${requestId}] Early failure in scheduled workflow ${payload.workflowId}`, error)
+    logger.error(
+      `[${requestId}] Early failure in scheduled workflow ${payload.workflowId}`,
+      error,
+      {
+        cause: describeError(error),
+      }
+    )
 
     if (wasExecutionFinalizedByCore(error, executionId)) {
       throw error
@@ -950,7 +956,9 @@ export async function executeScheduleJob(payload: ScheduleExecutionPayload) {
           return
         }
 
-        logger.error(`[${requestId}] Error processing schedule ${payload.scheduleId}`, error)
+        logger.error(`[${requestId}] Error processing schedule ${payload.scheduleId}`, error, {
+          cause: describeError(error),
+        })
         await releaseClaim(
           now,
           `Failed to release schedule ${payload.scheduleId} after unhandled error`
diff --git a/apps/sim/background/workflow-column-execution.ts b/apps/sim/background/workflow-column-execution.ts
index 53c337842fa..9f617cd5144 100644
--- a/apps/sim/background/workflow-column-execution.ts
+++ b/apps/sim/background/workflow-column-execution.ts
@@ -1,12 +1,13 @@
 import { db } from '@sim/db'
 import { workflow as workflowTable } from '@sim/db/schema'
 import { createLogger, runWithRequestContext } from '@sim/logger'
-import { toError } from '@sim/utils/errors'
+import { describeError, toError } from '@sim/utils/errors'
 import { sleep } from '@sim/utils/helpers'
 import { generateId } from '@sim/utils/id'
 import { backoffWithJitter } from '@sim/utils/retry'
 import { task } from '@trigger.dev/sdk'
 import { eq } from 'drizzle-orm'
+import { isRetryableInfrastructureError } from '@/lib/core/errors/retryable-infrastructure'
 import { createTimeoutAbortController } from '@/lib/core/execution-limits'
 import { RateLimiter } from '@/lib/core/rate-limiter/rate-limiter'
 import { preprocessExecution } from '@/lib/execution/preprocessing'
@@ -597,8 +598,8 @@ async function runWorkflowAndWriteTerminal(
           })
           .catch((err) => {
             logger.warn(
-              `Per-block partial write failed (table=${tableId} row=${rowId} group=${groupId}):`,
-              err
+              `Per-block partial write failed (table=${tableId} row=${rowId} group=${groupId})`,
+              { cause: describeError(err), retryable: isRetryableInfrastructureError(err) }
             )
           })
       }
@@ -720,7 +721,12 @@ async function runWorkflowAndWriteTerminal(
       const message = toError(err).message
       logger.error(
         `Workflow group cell execution failed (table=${tableId} row=${rowId} group=${groupId})`,
-        { error: message, executionId }
+        {
+          error: message,
+          executionId,
+          cause: describeError(err),
+          retryable: isRetryableInfrastructureError(err),
+        }
       )
       terminalWritten = true
       await writeChain.catch(() => {})
@@ -735,7 +741,11 @@ async function runWorkflowAndWriteTerminal(
           blockErrors,
         })
       } catch (writeErr) {
-        logger.error('Also failed to write error state', { error: toError(writeErr).message })
+        logger.error('Also failed to write error state', {
+          error: toError(writeErr).message,
+          cause: describeError(writeErr),
+          retryable: isRetryableInfrastructureError(writeErr),
+        })
       }
       return 'error'
     }
diff --git a/apps/sim/lib/logs/execution/logging-session.ts b/apps/sim/lib/logs/execution/logging-session.ts
index 09bfd2348ca..a0fd011dc7d 100644
--- a/apps/sim/lib/logs/execution/logging-session.ts
+++ b/apps/sim/lib/logs/execution/logging-session.ts
@@ -1,8 +1,9 @@
 import { db } from '@sim/db'
 import { workflowExecutionLogs } from '@sim/db/schema'
 import { createLogger } from '@sim/logger'
-import { toError } from '@sim/utils/errors'
+import { describeError, toError } from '@sim/utils/errors'
 import { and, eq, sql } from 'drizzle-orm'
+import { isRetryableInfrastructureError } from '@/lib/core/errors/retryable-infrastructure'
 import { executionLogger } from '@/lib/logs/execution/logger'
 import {
   calculateCostSummary,
@@ -177,6 +178,8 @@ export class LoggingSession {
     } catch (error) {
       logger.error(`Failed to persist last started block for execution ${this.executionId}:`, {
         error: toError(error).message,
+        cause: describeError(error),
+        retryable: isRetryableInfrastructureError(error),
       })
     }
   }
@@ -193,6 +196,8 @@ export class LoggingSession {
     } catch (error) {
       logger.error(`Failed to persist last completed block for execution ${this.executionId}:`, {
         error: toError(error).message,
+        cause: describeError(error),
+        retryable: isRetryableInfrastructureError(error),
       })
     }
   }
@@ -411,6 +416,8 @@ export class LoggingSession {
         executionId: this.executionId,
         error: toError(error).message,
         stack: error instanceof Error ? error.stack : undefined,
+        cause: describeError(error),
+        retryable: isRetryableInfrastructureError(error),
       })
       throw error
     }
@@ -1057,7 +1064,11 @@ export class LoggingSession {
       this.completionAttemptFailed = true
       logger.error(
         `[${this.requestId || 'unknown'}] Cost-only fallback also failed for execution ${this.executionId}:`,
-        { error: toError(fallbackError).message }
+        {
+          error: toError(fallbackError).message,
+          cause: describeError(fallbackError),
+          retryable: isRetryableInfrastructureError(fallbackError),
+        }
       )
     }
   }
diff --git a/apps/sim/lib/workflows/executor/pause-persistence.ts b/apps/sim/lib/workflows/executor/pause-persistence.ts
index 2080668cccd..954329ad4fa 100644
--- a/apps/sim/lib/workflows/executor/pause-persistence.ts
+++ b/apps/sim/lib/workflows/executor/pause-persistence.ts
@@ -1,5 +1,6 @@
 import { createLogger } from '@sim/logger'
-import { toError } from '@sim/utils/errors'
+import { describeError, toError } from '@sim/utils/errors'
+import { isRetryableInfrastructureError } from '@/lib/core/errors/retryable-infrastructure'
 import type { LoggingSession } from '@/lib/logs/execution/logging-session'
 import { PauseResumeManager } from '@/lib/workflows/executor/human-in-the-loop-manager'
 import type { ExecutionResult } from '@/executor/types'
@@ -46,6 +47,8 @@ export async function handlePostExecutionPauseState({
         logger.error('Failed to persist pause result', {
           executionId,
           error: toError(pauseError).message,
+          cause: describeError(pauseError),
+          retryable: isRetryableInfrastructureError(pauseError),
         })
         await loggingSession.markAsFailed(
           `Failed to persist pause state: ${toError(pauseError).message}`
@@ -59,6 +62,8 @@ export async function handlePostExecutionPauseState({
       logger.error('Failed to process queued resumes', {
         executionId,
         error: toError(resumeError).message,
+        cause: describeError(resumeError),
+        retryable: isRetryableInfrastructureError(resumeError),
       })
     }
   }
diff --git a/packages/utils/src/errors.test.ts b/packages/utils/src/errors.test.ts
index fa11dc191f9..272c85e53a4 100644
--- a/packages/utils/src/errors.test.ts
+++ b/packages/utils/src/errors.test.ts
@@ -2,7 +2,7 @@
  * @vitest-environment node
  */
 import { describe, expect, it } from 'vitest'
-import { getPostgresErrorCode, toError } from './errors.js'
+import { describeError, getPostgresErrorCode, toError } from './errors.js'
 
 describe('toError', () => {
   it('returns the same Error when given an Error', () => {
@@ -76,3 +76,54 @@ describe('getPostgresErrorCode', () => {
     expect(getPostgresErrorCode(err1)).toBeUndefined()
   })
 })
+
+describe('describeError', () => {
+  it('reports name and message for a plain error, omitting causeChain', () => {
+    const described = describeError(new Error('boom'))
+    expect(described).toEqual({ name: 'Error', message: 'boom' })
+    expect(described.causeChain).toBeUndefined()
+  })
+
+  it('surfaces the deepest cause for a wrapped driver error', () => {
+    const driver = Object.assign(new Error('read ECONNRESET'), {
+      code: 'ECONNRESET',
+      errno: 'ECONNRESET',
+      syscall: 'read',
+    })
+    const wrapped = new Error('Failed query: select ...', { cause: driver })
+    const described = describeError(wrapped)
+    expect(described.message).toBe('read ECONNRESET')
+    expect(described.code).toBe('ECONNRESET')
+    expect(described.errno).toBe('ECONNRESET')
+    expect(described.syscall).toBe('read')
+    expect(described.causeChain).toEqual([
+      'Error: Failed query: select ...',
+      'Error: read ECONNRESET',
+    ])
+  })
+
+  it('always returns the cause for unclassified errors (AbortError)', () => {
+    const aborted = Object.assign(new Error('The operation was aborted'), { name: 'AbortError' })
+    expect(describeError(aborted)).toEqual({
+      name: 'AbortError',
+      message: 'The operation was aborted',
+    })
+  })
+
+  it('falls back to a populated description for non-Error input without throwing', () => {
+    expect(describeError('just a string')).toEqual({ name: 'Error', message: 'just a string' })
+    expect(() => describeError({ weird: true })).not.toThrow()
+  })
+
+  it('stops at depth 10 and does not loop on a cyclic cause', () => {
+    const a = new Error('a')
+    const b = new Error('b')
+    ;(a as { cause?: unknown }).cause = b
+    ;(b as { cause?: unknown }).cause = a
+    let described: ReturnType<typeof describeError> | undefined
+    expect(() => {
+      described = describeError(a)
+    }).not.toThrow()
+    expect(described?.causeChain?.length).toBeLessThanOrEqual(10)
+  })
+})
diff --git a/packages/utils/src/errors.ts b/packages/utils/src/errors.ts
index 48fcee083c3..dc21d57b995 100644
--- a/packages/utils/src/errors.ts
+++ b/packages/utils/src/errors.ts
@@ -39,6 +39,60 @@ export function getPostgresConstraintName(error: unknown): string | undefined {
   return readPgErrorField(error, 'constraint_name') ?? readPgErrorField(error, 'constraint')
 }
 
+export interface DescribedError {
+  name: string
+  message: string
+  code?: string
+  errno?: string
+  syscall?: string
+  /** `"Name: message"` per link in the `.cause` chain, outermost first. Present only when the chain has more than one link. */
+  causeChain?: string[]
+}
+
+/**
+ * Always-on diagnostic view of an error and its `.cause` chain.
+ *
+ * Reports the fields of the DEEPEST `.cause` link, because a wrapped driver
+ * error (e.g. Drizzle's `"Failed query: ..."` wrapping an `ECONNRESET`) carries
+ * the real reason there, not on the outer wrapper. Always returns a populated
+ * object — including for non-`Error` throws and unclassified errors like
+ * `AbortError`. Cycle-safe and depth-bounded.
+ *
+ * Loggers do not serialize the non-enumerable `Error.prototype.cause`, so pass
+ * the result as an explicit structured field rather than the raw error.
+ */
+export function describeError(error: unknown): DescribedError {
+  const chain: Error[] = []
+  const seen = new Set<unknown>()
+  let current: unknown = error
+  while (current instanceof Error && !seen.has(current) && chain.length < 10) {
+    seen.add(current)
+    chain.push(current)
+    current = current.cause
+  }
+
+  if (chain.length === 0) {
+    const normalized = toError(error)
+    return { name: normalized.name, message: normalized.message }
+  }
+
+  const deepest = chain[chain.length - 1] as Error & Record<string, unknown>
+  const asString = (value: unknown): string | undefined =>
+    typeof value === 'string' ? value : undefined
+  const code = asString(deepest.code)
+  const errno = asString(deepest.errno)
+  const syscall = asString(deepest.syscall)
+
+  return {
+    name: deepest.name,
+    message: deepest.message,
+    ...(code ? { code } : {}),
+    ...(errno ? { errno } : {}),
+    ...(syscall ? { syscall } : {}),
+    ...(chain.length > 1 ? { causeChain: chain.map((e) => `${e.name}: ${e.message}`) } : {}),
+  }
+}
+
 function readPgErrorField(error: unknown, field: string): string | undefined {
   const seen = new Set<unknown>()
   let current: unknown = error