diff --git a/apps/sim/lib/workflows/comparison/compare.test.ts b/apps/sim/lib/workflows/comparison/compare.test.ts
index d78be67c55d..63811a90dc5 100644
--- a/apps/sim/lib/workflows/comparison/compare.test.ts
+++ b/apps/sim/lib/workflows/comparison/compare.test.ts
@@ -386,6 +386,39 @@ describe('hasWorkflowChanged', () => {
       expect(hasWorkflowChanged(unset, withErrorFlag(false))).toBe(false)
       expect(hasWorkflowChanged(unset, withErrorFlag(true))).toBe(true)
     })
+
+    /**
+     * `setBlockErrorEnabled` leaves existing error edges in place, so a block can
+     * hold `errorEnabled: false` with a connected error edge. Only the deployed
+     * side is backfilled (`materializeDeploymentState`), so reading the flag alone
+     * makes that block differ from itself, and redeploying cannot clear it — the
+     * snapshot stores the live `false` that the next read backfills to `true`.
+     */
+    const withErrorEdge = (errorEnabled: boolean) =>
+      createWorkflowState({
+        blocks: {
+          block1: { ...createBlock('block1'), errorEnabled },
+          block2: createBlock('block2'),
+        },
+        edges: [
+          { id: 'e1', source: 'block1', sourceHandle: 'error', target: 'block2' },
+        ] as WorkflowState['edges'],
+      })
+
+    it.concurrent('treats a live error edge as the flag being on', () => {
+      expect(hasWorkflowChanged(withErrorEdge(false), withErrorEdge(true))).toBe(false)
+      expect(hasWorkflowChanged(withErrorEdge(true), withErrorEdge(false))).toBe(false)
+    })
+
+    it.concurrent('reports no modified block when only the backfilled flag differs', () => {
+      const summary = generateWorkflowDiffSummary(withErrorEdge(false), withErrorEdge(true))
+      expect(summary.hasChanges).toBe(false)
+      expect(summary.modifiedBlocks).toEqual([])
+    })
+
+    it.concurrent('still detects the flag turning on when no error edge exists', () => {
+      expect(hasWorkflowChanged(withErrorFlag(true), withErrorFlag(false))).toBe(true)
+    })
   })
 
   describe('SubBlock Changes', () => {
diff --git a/apps/sim/lib/workflows/comparison/compare.ts b/apps/sim/lib/workflows/comparison/compare.ts
index b2a3d300960..e030e1b13aa 100644
--- a/apps/sim/lib/workflows/comparison/compare.ts
+++ b/apps/sim/lib/workflows/comparison/compare.ts
@@ -1,5 +1,9 @@
 import { createLogger } from '@sim/logger'
-import { blockRetryEquals } from '@sim/workflow-types/workflow'
+import {
+  blockRetryEquals,
+  collectErrorSourceBlockIds,
+  resolveEffectiveErrorEnabled,
+} from '@sim/workflow-types/workflow'
 import type { WorkflowState } from '@/stores/workflows/workflow/types'
 import {
   extractBlockFieldsForComparison,
@@ -132,6 +136,8 @@ export function generateWorkflowDiffSummary(
   const previousBlocks = previousState.blocks || {}
   const currentBlockIds = new Set(Object.keys(currentBlocks))
   const previousBlockIds = new Set(Object.keys(previousBlocks))
+  const currentErrorSources = collectErrorSourceBlockIds(currentState.edges)
+  const previousErrorSources = collectErrorSourceBlockIds(previousState.edges)
 
   for (const id of currentBlockIds) {
     if (!previousBlockIds.has(id)) {
@@ -173,6 +179,25 @@ export function generateWorkflowDiffSummary(
       subBlocks: previousSubBlocks,
     } = extractBlockFieldsForComparison(previousBlock)
 
+    /**
+     * Outside the structural gate below: the flag alone can match while the edges
+     * disagree, and reading it alone pins a block with a stale `errorEnabled: false`
+     * and a live error edge to "needs redeploy" forever.
+     */
+    const currentErrorEnabled = resolveEffectiveErrorEnabled(currentBlock, id, currentErrorSources)
+    const previousErrorEnabled = resolveEffectiveErrorEnabled(
+      previousBlock,
+      id,
+      previousErrorSources
+    )
+    if (currentErrorEnabled !== previousErrorEnabled) {
+      changes.push({
+        field: 'errorEnabled',
+        oldValue: previousErrorEnabled,
+        newValue: currentErrorEnabled,
+      })
+    }
+
     const normalizedCurrentBlock = { ...currentRest, data: currentDataRest, subBlocks: undefined }
     const normalizedPreviousBlock = {
       ...previousRest,
@@ -196,12 +221,8 @@ export function generateWorkflowDiffSummary(
           newValue: currentBlock.enabled,
         })
       }
-      const blockFields = [
-        'horizontalHandles',
-        'advancedMode',
-        'triggerMode',
-        'errorEnabled',
-      ] as const
+      /** `errorEnabled` is compared above, against the edges as well as the flag. */
+      const blockFields = ['horizontalHandles', 'advancedMode', 'triggerMode'] as const
       for (const field of blockFields) {
         if (!!currentBlock[field] !== !!previousBlock[field]) {
           changes.push({
diff --git a/apps/sim/lib/workflows/persistence/utils.ts b/apps/sim/lib/workflows/persistence/utils.ts
index c9313ef325d..9150443d5d2 100644
--- a/apps/sim/lib/workflows/persistence/utils.ts
+++ b/apps/sim/lib/workflows/persistence/utils.ts
@@ -17,7 +17,10 @@ import {
 import { saveWorkflowToNormalizedTables as saveWorkflowToNormalizedTablesRaw } from '@sim/workflow-persistence/save'
 import type { DbOrTx, NormalizedWorkflowData } from '@sim/workflow-persistence/types'
 import type { BlockState, Loop, Parallel, WorkflowState } from '@sim/workflow-types/workflow'
-import { normalizeWorkflowEdgeHandles } from '@sim/workflow-types/workflow'
+import {
+  collectErrorSourceBlockIds,
+  normalizeWorkflowEdgeHandles,
+} from '@sim/workflow-types/workflow'
 import type { InferSelectModel } from 'drizzle-orm'
 import { and, desc, eq, inArray, lt, sql } from 'drizzle-orm'
 import { LRUCache } from 'lru-cache'
@@ -181,18 +184,18 @@ async function materializeDeploymentState(
    */
   const edges = normalizeWorkflowEdgeHandles(state.edges)
 
-  /*
+  /**
    * An error edge means the error output is on. Every version before the toggle
    * drew that port unconditionally, so a snapshot with such an edge was taken
    * from a block that had the output — and the migration backfilling the flag
    * only reaches the live tables, never a version's frozen jsonb. Without this
    * the deployed side reads `false` against a live `true` and every workflow
-   * deployed before the toggle asks to be redeployed once. Same rule as
-   * `workflow-block.tsx` applies at render time; neither may read the flag alone.
+   * deployed before the toggle asks to be redeployed once. This backfills only
+   * the deployed side, so change detection must apply `resolveEffectiveErrorEnabled`
+   * to the live side too — reading the raw flag there compares a block against
+   * itself forever. Same rule the block renderers apply; none may read the flag alone.
    */
-  const errorSourceBlockIds = new Set(
-    edges.filter((edge) => edge.sourceHandle === 'error').map((edge) => edge.source)
-  )
+  const errorSourceBlockIds = collectErrorSourceBlockIds(edges)
   const blocks: DeployedWorkflowData['blocks'] = {}
   for (const [blockId, block] of Object.entries(migratedBlocks)) {
     blocks[blockId] =
diff --git a/packages/workflow-types/src/workflow.ts b/packages/workflow-types/src/workflow.ts
index b1ba622d14e..0d1b19729af 100644
--- a/packages/workflow-types/src/workflow.ts
+++ b/packages/workflow-types/src/workflow.ts
@@ -342,6 +342,8 @@ export type WorkflowConnectionSide = (typeof WORKFLOW_CONNECTION_SIDES)[number]
 export const WORKFLOW_SOURCE_HANDLE_ID = 'source'
 /** The one input handle every block that accepts a connection exposes. */
 export const WORKFLOW_TARGET_HANDLE_ID = 'target'
+/** The output handle a block's error branch leaves through. */
+export const WORKFLOW_ERROR_HANDLE_ID = 'error'
 
 /**
  * Side-anchored handle ids (`source-right`, `target-left`, …) briefly existed
@@ -387,6 +389,45 @@ export function normalizeWorkflowEdgeTargetHandle(
   return canonical
 }
 
+/**
+ * Collects the ids of blocks an error edge leaves, canonicalizing handles first
+ * so the set is the same however the edge list was loaded.
+ */
+export function collectErrorSourceBlockIds(
+  edges: readonly WorkflowEdgeHandles[] | null | undefined
+): Set<string> {
+  const sources = new Set<string>()
+  for (const edge of edges || []) {
+    if (normalizeWorkflowEdgeSourceHandle(edge.sourceHandle) === WORKFLOW_ERROR_HANDLE_ID) {
+      sources.add(edge.source)
+    }
+  }
+  return sources
+}
+
+/**
+ * Whether a block's error output is on, read from the edges as well as the flag.
+ *
+ * An error edge means the port is live whatever the flag says: `setBlockErrorEnabled`
+ * leaves existing error edges in place, and both block renderers draw the port on
+ * `errorEnabled || hasErrorConnection`, so a block can sit at `errorEnabled: false`
+ * with a connected error edge indefinitely. The executor never reads the flag at
+ * all — the edge alone decides routing — so the two spellings are one state.
+ *
+ * Every reader that compares or materializes a block must apply this rule rather
+ * than the flag alone. Applying it on one side only is what pinned a workflow to
+ * "needs redeploy" with nothing to deploy: change detection read a backfilled
+ * `true` against a live `false`, and redeploying snapshotted the live `false` that
+ * the next read backfilled straight back to `true`.
+ */
+export function resolveEffectiveErrorEnabled(
+  block: Pick<BlockState, 'errorEnabled'>,
+  blockId: string,
+  errorSourceBlockIds: ReadonlySet<string>
+): boolean {
+  return Boolean(block.errorEnabled) || errorSourceBlockIds.has(blockId)
+}
+
 /**
  * Canonicalizes a whole edge list, for the readers that bypass
  * `loadWorkflowFromNormalizedTables` — deployment-version blobs, run