Surface scheduled retry cancel failures

Co-Authored-By: Paperclip <noreply@paperclip.ing>

server/src/__tests__/issue-comment-reopen-routes.test.ts

@@ -635,6 +635,40 @@ describe.sequential("issue comment reopen routes", () => {
     ));
   });
 
+  it("does not move scheduled-retry issues to todo when POST comment retry cancellation fails", async () => {
+    const issue = {
+      ...makeIssue("in_progress"),
+      executionRunId: "retry-run-1",
+    };
+    mockIssueService.getById.mockResolvedValue(issue);
+    mockIssueService.getCurrentScheduledRetry.mockResolvedValue({
+      runId: "retry-run-1",
+      status: "scheduled_retry",
+      agentId: "22222222-2222-4222-8222-222222222222",
+      agentName: "CodexCoder",
+      retryOfRunId: "source-run-1",
+      scheduledRetryAt: new Date("2026-05-18T14:00:00.000Z"),
+      scheduledRetryAttempt: 1,
+      scheduledRetryReason: "transient_failure",
+      error: null,
+      errorCode: null,
+    });
+    mockHeartbeatService.cancelRun.mockRejectedValue(new Error("cancel failed"));
+
+    const res = await request(await installActor(createApp()))
+      .post("/api/issues/11111111-1111-4111-8111-111111111111/comments")
+      .send({ body: "I added the missing detail; please continue." });
+
+    expect(res.status).toBe(500);
+    expect(mockHeartbeatService.cancelRun).toHaveBeenCalledWith("retry-run-1");
+    expect(mockIssueService.update).not.toHaveBeenCalled();
+    expect(mockIssueService.addComment).not.toHaveBeenCalled();
+    expect(mockLogActivity).not.toHaveBeenCalledWith(
+      expect.anything(),
+      expect.objectContaining({ action: "issue.updated" }),
+    );
+  });
+
   it("keeps ordinary in-progress POST human comments in progress when no scheduled retry exists", async () => {
     const issue = makeIssue("in_progress");
     mockIssueService.getById.mockResolvedValue(issue);
@@ -874,6 +908,40 @@ describe.sequential("issue comment reopen routes", () => {
     ));
   });
 
+  it("does not move scheduled-retry issues to todo when PATCH comment retry cancellation fails", async () => {
+    const issue = {
+      ...makeIssue("in_progress"),
+      executionRunId: "retry-run-1",
+    };
+    mockIssueService.getById.mockResolvedValue(issue);
+    mockIssueService.getCurrentScheduledRetry.mockResolvedValue({
+      runId: "retry-run-1",
+      status: "scheduled_retry",
+      agentId: "22222222-2222-4222-8222-222222222222",
+      agentName: "CodexCoder",
+      retryOfRunId: "source-run-1",
+      scheduledRetryAt: new Date("2026-05-18T14:00:00.000Z"),
+      scheduledRetryAttempt: 1,
+      scheduledRetryReason: "transient_failure",
+      error: null,
+      errorCode: null,
+    });
+    mockHeartbeatService.cancelRun.mockRejectedValue(new Error("cancel failed"));
+
+    const res = await request(await installActor(createApp()))
+      .patch("/api/issues/11111111-1111-4111-8111-111111111111")
+      .send({ comment: "Retry window is over; please continue." });
+
+    expect(res.status).toBe(500);
+    expect(mockHeartbeatService.cancelRun).toHaveBeenCalledWith("retry-run-1");
+    expect(mockIssueService.update).not.toHaveBeenCalled();
+    expect(mockIssueService.addComment).not.toHaveBeenCalled();
+    expect(mockLogActivity).not.toHaveBeenCalledWith(
+      expect.anything(),
+      expect.objectContaining({ action: "issue.updated" }),
+    );
+  });
+
   it("rejects non-assignee agent PATCH comments on closed issues", async () => {
     mockIssueService.getById.mockResolvedValue(makeIssue("done"));
     mockIssueService.addComment.mockResolvedValue({

server/src/routes/issues.ts

@@ -912,11 +912,11 @@ export function issueRoutes(
       });
       return cancelledRunId;
     } catch (err) {
-      logger.warn(
+      logger.error(
         { err, issueId: input.issue.id, runId: scheduledRetryRunId },
         "failed to cancel scheduled retry superseded by issue comment",
       );
-      return null;
+      throw err;
     }
   }
 
@@ -3534,6 +3534,18 @@ export function issueRoutes(
     ) {
       updateFields.status = "todo";
     }
+    let cancelledScheduledRetryRunId: string | null = null;
+    if (
+      commentBody &&
+      shouldResumeInProgressScheduledRetry &&
+      updateFields.status === "todo"
+    ) {
+      cancelledScheduledRetryRunId = await cancelScheduledRetrySupersededByComment({
+        scheduledRetryRunId: scheduledRetryForHumanComment?.runId,
+        issue: existing,
+        actor,
+      });
+    }
     if (req.body.executionPolicy !== undefined) {
       updateFields.executionPolicy = applyActorMonitorScheduledBy(
         normalizeIssueExecutionPolicy(req.body.executionPolicy),
@@ -3792,13 +3804,6 @@ export function issueRoutes(
       previous.status !== undefined &&
       existing.status === "in_progress" &&
       issue.status === "todo";
-    const cancelledScheduledRetryRunId = scheduledRetrySupersededByComment
-      ? await cancelScheduledRetrySupersededByComment({
-          scheduledRetryRunId: scheduledRetryForHumanComment?.runId,
-          issue,
-          actor,
-        })
-      : null;
     const statusChangedFromBlockedToTodo =
       existing.status === "blocked" &&
       issue.status === "todo" &&
@@ -5125,22 +5130,22 @@ export function issueRoutes(
       effectiveMoveToTodoRequested &&
       (isClosed || (isBlocked && !hasUnresolvedFirstClassBlockers) || shouldResumeInProgressScheduledRetry)
     ) {
+      scheduledRetrySupersededByComment = shouldResumeInProgressScheduledRetry && issue.status === "in_progress";
+      cancelledScheduledRetryRunId = scheduledRetrySupersededByComment
+        ? await cancelScheduledRetrySupersededByComment({
+            scheduledRetryRunId: scheduledRetryForHumanComment?.runId,
+            issue,
+            actor,
+          })
+        : null;
       const reopenedIssue = await svc.update(id, { status: "todo" });
       if (!reopenedIssue) {
         res.status(404).json({ error: "Issue not found" });
         return;
       }
       reopened = isClosed || (isBlocked && !hasUnresolvedFirstClassBlockers);
-      scheduledRetrySupersededByComment = shouldResumeInProgressScheduledRetry && issue.status === "in_progress";
       reopenFromStatus = reopened ? issue.status : null;
       currentIssue = reopenedIssue;
-      cancelledScheduledRetryRunId = scheduledRetrySupersededByComment
-        ? await cancelScheduledRetrySupersededByComment({
-            scheduledRetryRunId: scheduledRetryForHumanComment?.runId,
-            issue: currentIssue,
-            actor,
-          })
-        : null;
 
       await logActivity(db, {
         companyId: currentIssue.companyId,