Fix continuation recovery escalation gating

server/src/__tests__/heartbeat-process-recovery.test.ts

@@ -308,6 +308,9 @@ describeEmbeddedPostgres("heartbeat orphaned process recovery", () => {
     runStatus: "failed" | "timed_out" | "cancelled" | "succeeded";
     retryReason?: "assignment_recovery" | "issue_continuation_needed" | null;
     assignToUser?: boolean;
+    runErrorCode?: string | null;
+    runError?: string | null;
+    resultJson?: Record<string, unknown> | null;
   }) {
     const companyId = randomUUID();
     const agentId = randomUUID();
@@ -348,7 +351,10 @@ describeEmbeddedPostgres("heartbeat orphaned process recovery", () => {
       runId,
       claimedAt: now,
       finishedAt: new Date("2026-03-19T00:05:00.000Z"),
-      error: input.runStatus === "succeeded" ? null : "run failed before issue advanced",
+      error:
+        input.runStatus === "succeeded"
+          ? null
+          : (input.runError ?? "run failed before issue advanced"),
     });
 
     await db.insert(heartbeatRuns).values({
@@ -370,8 +376,15 @@ describeEmbeddedPostgres("heartbeat orphaned process recovery", () => {
       startedAt: now,
       finishedAt: new Date("2026-03-19T00:05:00.000Z"),
       updatedAt: new Date("2026-03-19T00:05:00.000Z"),
-      errorCode: input.runStatus === "succeeded" ? null : "process_lost",
-      error: input.runStatus === "succeeded" ? null : "run failed before issue advanced",
+      errorCode:
+        input.runStatus === "succeeded"
+          ? null
+          : (input.runErrorCode ?? "process_lost"),
+      error:
+        input.runStatus === "succeeded"
+          ? null
+          : (input.runError ?? "run failed before issue advanced"),
+      resultJson: input.resultJson ?? null,
     });
 
     await db.insert(issues).values({
@@ -632,6 +645,10 @@ describeEmbeddedPostgres("heartbeat orphaned process recovery", () => {
       status: "in_progress",
       runStatus: "failed",
       retryReason: "issue_continuation_needed",
+      runErrorCode: "adapter_failed",
+      resultJson: {
+        summary: "OpenAI API request failed with 429 rate_limit_exceeded",
+      },
     });
     const heartbeat = heartbeatService(db);
 
@@ -646,6 +663,31 @@ describeEmbeddedPostgres("heartbeat orphaned process recovery", () => {
     const comments = await db.select().from(issueComments).where(eq(issueComments.issueId, issueId));
     expect(comments).toHaveLength(1);
     expect(comments[0]?.body).toContain("retried continuation");
+    expect(comments[0]?.body).toContain(
+      "Latest failure summary: adapter_failed: OpenAI API request failed with 429 rate_limit_exceeded",
+    );
+  });
+
+  it("does not block stranded in-progress work after a successful continuation retry", async () => {
+    const { issueId } = await seedStrandedIssueFixture({
+      status: "in_progress",
+      runStatus: "succeeded",
+      retryReason: "issue_continuation_needed",
+    });
+    const heartbeat = heartbeatService(db);
+
+    const result = await heartbeat.reconcileStrandedAssignedIssues();
+    expect(result.dispatchRequeued).toBe(0);
+    expect(result.continuationRequeued).toBe(0);
+    expect(result.escalated).toBe(0);
+    expect(result.skipped).toBe(1);
+    expect(result.issueIds).toEqual([]);
+
+    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);
   });
 
   it("does not reconcile user-assigned work through the agent stranded-work recovery path", async () => {

server/src/services/heartbeat.ts

@@ -92,6 +92,7 @@ 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 FAILED_CONTINUATION_RECOVERY_STATUSES = new Set(["failed", "timed_out", "cancelled"]);
 const SESSIONED_LOCAL_ADAPTERS = new Set([
   "claude_local",
   "codex_local",
@@ -519,6 +520,12 @@ function readNonEmptyString(value: unknown): string | null {
   return typeof value === "string" && value.trim().length > 0 ? value : null;
 }
 
+function readFirstSummaryLine(value: unknown): string | null {
+  const text = readNonEmptyString(value);
+  if (!text) return null;
+  return text.split(/\r?\n/, 1)[0]?.trim() ?? null;
+}
+
 function normalizeLedgerBillingType(value: unknown): BillingType {
   const raw = readNonEmptyString(value);
   switch (raw) {
@@ -2768,6 +2775,42 @@ export function heartbeatService(db: Db) {
     return queued;
   }
 
+  function didContinuationRecoveryFail(
+    latestRun: typeof heartbeatRuns.$inferSelect | null,
+    latestRetryReason: string | null,
+  ) {
+    return Boolean(
+      latestRun &&
+        latestRetryReason === "issue_continuation_needed" &&
+        FAILED_CONTINUATION_RECOVERY_STATUSES.has(latestRun.status),
+    );
+  }
+
+  function formatLatestRunFailureSummary(latestRun: typeof heartbeatRuns.$inferSelect | null) {
+    if (!latestRun) return null;
+
+    const latestSummary = summarizeHeartbeatRunResultJson(latestRun.resultJson);
+    const summaryLine =
+      readFirstSummaryLine(latestSummary?.summary) ??
+      readFirstSummaryLine(latestSummary?.result) ??
+      readFirstSummaryLine(latestSummary?.message) ??
+      readFirstSummaryLine(latestSummary?.error) ??
+      readFirstSummaryLine(latestRun.error);
+    const errorCode = readNonEmptyString(latestRun.errorCode);
+
+    if (errorCode && summaryLine) return `${errorCode}: ${summaryLine}`;
+    return summaryLine ?? errorCode;
+  }
+
+  function buildStrandedAssignedIssueComment(input: {
+    baseComment: string;
+    latestRun: typeof heartbeatRuns.$inferSelect | null;
+  }) {
+    const failureSummary = formatLatestRunFailureSummary(input.latestRun);
+    if (!failureSummary) return input.baseComment;
+    return `${input.baseComment}\n\nLatest failure summary: ${failureSummary}`;
+  }
+
   async function escalateStrandedAssignedIssue(input: {
     issue: typeof issues.$inferSelect;
     previousStatus: "todo" | "in_progress";
@@ -2861,9 +2904,12 @@ export function heartbeatService(db: Db) {
             issue,
             previousStatus: "todo",
             latestRun,
-            comment:
-              "Paperclip automatically retried dispatch for this assigned `todo` issue after a lost wake/run, " +
-              "but it still has no live execution path. Moving it to `blocked` so it is visible for intervention.",
+            comment: buildStrandedAssignedIssueComment({
+              latestRun,
+              baseComment:
+                "Paperclip automatically retried dispatch for this assigned `todo` issue after a lost wake/run, " +
+                "but it still has no live execution path. Moving it to `blocked` so it is visible for intervention.",
+            }),
           });
           if (updated) {
             result.escalated += 1;
@@ -2891,15 +2937,18 @@ export function heartbeatService(db: Db) {
         continue;
       }
 
-      if (latestRetryReason === "issue_continuation_needed") {
+      if (didContinuationRecoveryFail(latestRun, latestRetryReason)) {
         const updated = await escalateStrandedAssignedIssue({
           issue,
           previousStatus: "in_progress",
           latestRun,
-          comment:
-            "Paperclip automatically retried continuation for this assigned `in_progress` issue after its live " +
-            "execution disappeared, but it still has no live execution path. Moving it to `blocked` so it is " +
-            "visible for intervention.",
+          comment: buildStrandedAssignedIssueComment({
+            latestRun,
+            baseComment:
+              "Paperclip automatically retried continuation for this assigned `in_progress` issue after its live " +
+              "execution disappeared, but it still has no live execution path. Moving it to `blocked` so it is " +
+              "visible for intervention.",
+          }),
         });
         if (updated) {
           result.escalated += 1;
@@ -2910,6 +2959,11 @@ export function heartbeatService(db: Db) {
         continue;
       }
 
+      if (latestRetryReason === "issue_continuation_needed" && latestRun?.status === "succeeded") {
+        result.skipped += 1;
+        continue;
+      }
+
       const queued = await enqueueStrandedIssueRecovery({
         issueId: issue.id,
         agentId,