diff --git a/server/src/__tests__/heartbeat-process-recovery.test.ts b/server/src/__tests__/heartbeat-process-recovery.test.ts
index 5d907470fa4..0bd61ba0422 100644
--- a/server/src/__tests__/heartbeat-process-recovery.test.ts
+++ b/server/src/__tests__/heartbeat-process-recovery.test.ts
@@ -651,6 +651,39 @@ describeEmbeddedPostgres("heartbeat orphaned process recovery", () => {
     expect(comments[0]?.body).toContain("Latest retry failure: `process_lost` - run failed before issue advanced.");
   });
 
+  it("re-enqueues continuation when the latest automatic continuation succeeded without closing the issue", async () => {
+    const { agentId, issueId, runId } = await seedStrandedIssueFixture({
+      status: "in_progress",
+      runStatus: "succeeded",
+      retryReason: "issue_continuation_needed",
+    });
+    const heartbeat = heartbeatService(db);
+
+    const result = await heartbeat.reconcileStrandedAssignedIssues();
+    expect(result.continuationRequeued).toBe(1);
+    expect(result.escalated).toBe(0);
+    expect(result.issueIds).toEqual([issueId]);
+
+    const issue = await db.select().from(issues).where(eq(issues.id, issueId)).then((rows) => rows[0] ?? null);
+    expect(issue?.status).toBe("in_progress");
+
+    const comments = await db.select().from(issueComments).where(eq(issueComments.issueId, issueId));
+    expect(comments).toHaveLength(0);
+
+    const runs = await db
+      .select()
+      .from(heartbeatRuns)
+      .where(eq(heartbeatRuns.agentId, agentId));
+    expect(runs).toHaveLength(2);
+
+    const retryRun = runs.find((row) => row.id !== runId);
+    expect(retryRun?.id).toBeTruthy();
+    expect((retryRun?.contextSnapshot as Record<string, unknown>)?.retryReason).toBe("issue_continuation_needed");
+    if (retryRun) {
+      await waitForRunToSettle(heartbeat, retryRun.id);
+    }
+  });
+
   it("does not reconcile user-assigned work through the agent stranded-work recovery path", async () => {
     const { issueId, runId } = await seedStrandedIssueFixture({
       status: "todo",
diff --git a/server/src/services/heartbeat.ts b/server/src/services/heartbeat.ts
index 02d108bb658..af9c568697d 100644
--- a/server/src/services/heartbeat.ts
+++ b/server/src/services/heartbeat.ts
@@ -94,6 +94,7 @@ const MAX_INLINE_WAKE_COMMENT_BODY_CHARS = 4_000;
 const MAX_INLINE_WAKE_COMMENT_BODY_TOTAL_CHARS = 12_000;
 const execFile = promisify(execFileCallback);
 const ACTIVE_HEARTBEAT_RUN_STATUSES = ["queued", "running"] as const;
+const UNSUCCESSFUL_HEARTBEAT_RUN_TERMINAL_STATUSES = ["failed", "cancelled", "timed_out"] as const;
 const SESSIONED_LOCAL_ADAPTERS = new Set([
   "claude_local",
   "codex_local",
@@ -681,6 +682,22 @@ function summarizeRunFailureForIssueComment(
   return null;
 }
 
+function didAutomaticRecoveryFail(
+  latestRun: Pick<typeof heartbeatRuns.$inferSelect, "status" | "contextSnapshot"> | null,
+  expectedRetryReason: "assignment_recovery" | "issue_continuation_needed",
+) {
+  if (!latestRun) return false;
+
+  const latestContext = parseObject(latestRun.contextSnapshot);
+  const latestRetryReason = readNonEmptyString(latestContext.retryReason);
+  return (
+    latestRetryReason === expectedRetryReason &&
+    UNSUCCESSFUL_HEARTBEAT_RUN_TERMINAL_STATUSES.includes(
+      latestRun.status as (typeof UNSUCCESSFUL_HEARTBEAT_RUN_TERMINAL_STATUSES)[number],
+    )
+  );
+}
+
 function normalizeLedgerBillingType(value: unknown): BillingType {
   const raw = readNonEmptyString(value);
   switch (raw) {
@@ -3037,16 +3054,13 @@ export function heartbeatService(db: Db) {
       }
 
       const latestRun = await getLatestIssueRun(issue.companyId, issue.id);
-      const latestContext = parseObject(latestRun?.contextSnapshot);
-      const latestRetryReason = readNonEmptyString(latestContext.retryReason);
-
       if (issue.status === "todo") {
         if (!latestRun || latestRun.status === "succeeded") {
           result.skipped += 1;
           continue;
         }
 
-        if (latestRetryReason === "assignment_recovery") {
+        if (didAutomaticRecoveryFail(latestRun, "assignment_recovery")) {
           const failureSummary = summarizeRunFailureForIssueComment(latestRun);
           const updated = await escalateStrandedAssignedIssue({
             issue,
@@ -3083,7 +3097,7 @@ export function heartbeatService(db: Db) {
         continue;
       }
 
-      if (latestRetryReason === "issue_continuation_needed") {
+      if (didAutomaticRecoveryFail(latestRun, "issue_continuation_needed")) {
         const failureSummary = summarizeRunFailureForIssueComment(latestRun);
         const updated = await escalateStrandedAssignedIssue({
           issue,