Clear stale monitor execution state

src/worker.ts

@@ -8133,8 +8133,30 @@ function isHealthyMaintainerWaitTransition(params: {
 
   return nextStatus === 'in_review'
     && (currentStatus === 'done' || currentStatus === 'in_review')
-    && syncContext.executionState === null
-    && syncContext.executionPolicy !== null;
+    && isClearableMaintainerWaitExecutionState(syncContext.executionState);
+}
+
+function isClearableMaintainerWaitExecutionState(
+  executionState: PaperclipIssueExecutionState | null
+): boolean {
+  if (executionState === null) {
+    return true;
+  }
+
+  if (
+    executionState.currentParticipant !== null ||
+    executionState.returnAssignee !== null ||
+    executionState.currentStageId !== null ||
+    executionState.currentStageIndex !== null ||
+    executionState.currentStageType !== null ||
+    executionState.completedStageIds.length > 0 ||
+    executionState.lastDecisionId ||
+    executionState.lastDecisionOutcome
+  ) {
+    return false;
+  }
+
+  return !executionState.status || executionState.status === 'idle' || executionState.status === 'completed';
 }
 
 function shouldClearCompletedSyncExecutionPolicy(params: {
@@ -12967,6 +12989,28 @@ async function updatePaperclipIssueState(
 
       if (!payloadResult.failure) {
         issueUpdated = true;
+        if (
+          issuePatch.executionState === null &&
+          ctx.issues &&
+          typeof ctx.issues.update === 'function'
+        ) {
+          try {
+            await ctx.issues.update(
+              issueId,
+              { executionState: null } as PaperclipIssueUpdatePatchWithLabels,
+              companyId
+            );
+          } catch (error) {
+            issueUpdated = false;
+            ctx.logger.warn('GitHub sync could not clear Paperclip issue execution state after the local API update. Falling back to direct issue mutation.', {
+              companyId,
+              issueId,
+              paperclipApiBaseUrl,
+              nextStatus,
+              error: getErrorMessage(error)
+            });
+          }
+        }
       }
 
       if (payloadResult.failure && (payloadResult.failure.status ?? response.status) !== 404 && (payloadResult.failure.status ?? response.status) !== 405) {

tests/plugin.spec.ts

@@ -18834,6 +18834,41 @@ test('worker routes non-review-ready GitHub merge state statuses back to active
       mergeStateStatus: 'UNKNOWN',
       expectedStatus: 'in_review' as const,
       expectedReason: /unknown mergeability/
+    },
+    {
+      githubIssueId: 5001,
+      githubIssueNumber: 50,
+      pullRequestNumber: 500,
+      title: 'Triggered monitor wait',
+      initialStatus: 'in_review' as const,
+      initialExecutionState: {
+        status: 'idle',
+        currentStageId: null,
+        currentStageIndex: null,
+        currentStageType: null,
+        currentParticipant: null,
+        returnAssignee: null,
+        completedStageIds: [],
+        lastDecisionId: null,
+        lastDecisionOutcome: null,
+        monitor: {
+          status: 'triggered',
+          nextCheckAt: null,
+          lastTriggeredAt: '2026-04-09T09:10:00.000Z',
+          attemptCount: 1,
+          notes: 'Check GitHub pull request status.',
+          scheduledBy: 'board',
+          kind: 'external_service',
+          serviceName: 'GitHub',
+          externalRef: null,
+          timeoutAt: null,
+          maxAttempts: null,
+          recoveryPolicy: null,
+          clearedAt: null,
+          clearReason: null
+        }
+      },
+      expectedStatus: 'in_review' as const
     }
   ];
 
@@ -18846,9 +18881,16 @@ test('worker routes non-review-ready GitHub merge state statuses back to active
       });
 
       const initialStatus = scenario.initialStatus ?? 'in_review';
-      return created.status === initialStatus
+      const patch: Record<string, unknown> = {
+        ...(created.status === initialStatus ? {} : { status: initialStatus }),
+        ...(scenario.initialExecutionState ? {
+          assigneeAgentId: 'agent-1',
+          executionState: scenario.initialExecutionState
+        } : {})
+      };
+      return Object.keys(patch).length === 0
         ? created
-        : harness.ctx.issues.update(created.id, { status: initialStatus }, 'company-1');
+        : harness.ctx.issues.update(created.id, patch as never, 'company-1');
     })
   );
 
@@ -19010,6 +19052,9 @@ test('worker routes non-review-ready GitHub merge state statuses back to active
         );
       } else {
         assert.equal(issue?.assigneeAgentId ?? null, null);
+        if (scenario.initialExecutionState) {
+          assert.equal(issue?.executionState ?? null, null);
+        }
         const transitionComment = statusTransitionComments.find((comment) => comment.issueId === issue?.id);
         if (scenario.initialStatus === 'done') {
           assert.match(transitionComment?.body ?? '', /from `done` to `in review`/);