diff --git a/server/src/__tests__/heartbeat-process-recovery.test.ts b/server/src/__tests__/heartbeat-process-recovery.test.ts
index a2faad9fd81..211f119a110 100644
--- a/server/src/__tests__/heartbeat-process-recovery.test.ts
+++ b/server/src/__tests__/heartbeat-process-recovery.test.ts
@@ -1417,6 +1417,42 @@ describeEmbeddedPostgres("heartbeat orphaned process recovery", () => {
     }
   });
 
+  it("still re-enqueues stranded assigned todo recovery when an old queued wake exists", async () => {
+    const { companyId, agentId, issueId, runId } = await seedStrandedIssueFixture({
+      status: "todo",
+      runStatus: "failed",
+    });
+    await db.insert(agentWakeupRequests).values({
+      companyId,
+      agentId,
+      source: "assignment",
+      triggerDetail: "system",
+      reason: "issue_assigned",
+      payload: { issueId },
+      status: "queued",
+    });
+    const heartbeat = heartbeatService(db);
+
+    const result = await heartbeat.reconcileStrandedAssignedIssues();
+    expect(result.assignmentDispatched).toBe(0);
+    expect(result.dispatchRequeued).toBe(1);
+    expect(result.continuationRequeued).toBe(0);
+    expect(result.escalated).toBe(0);
+    expect(result.issueIds).toEqual([issueId]);
+
+    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?.contextSnapshot as Record<string, unknown>)?.retryReason).toBe("assignment_recovery");
+    if (retryRun) {
+      await waitForRunToSettle(heartbeat, retryRun.id);
+    }
+  });
+
   it("blocks assigned todo work after the one automatic dispatch recovery was already used", async () => {
     const { companyId, agentId, issueId, runId } = await seedStrandedIssueFixture({
       status: "todo",
diff --git a/server/src/services/recovery/service.ts b/server/src/services/recovery/service.ts
index f239195058e..40d12555a9c 100644
--- a/server/src/services/recovery/service.ts
+++ b/server/src/services/recovery/service.ts
@@ -332,7 +332,7 @@ export function recoveryService(db: Db, deps: { enqueueWakeup: RecoveryWakeup })
         .where(
           and(
             eq(agentWakeupRequests.companyId, companyId),
-            inArray(agentWakeupRequests.status, ["queued", "deferred_issue_execution"]),
+            eq(agentWakeupRequests.status, "deferred_issue_execution"),
             sql`${agentWakeupRequests.payload} ->> 'issueId' = ${issueId}`,
           ),
         )
@@ -343,6 +343,21 @@ export function recoveryService(db: Db, deps: { enqueueWakeup: RecoveryWakeup })
     return Boolean(run || deferredWake);
   }
 
+  async function hasQueuedIssueWake(companyId: string, issueId: string) {
+    return db
+      .select({ id: agentWakeupRequests.id })
+      .from(agentWakeupRequests)
+      .where(
+        and(
+          eq(agentWakeupRequests.companyId, companyId),
+          eq(agentWakeupRequests.status, "queued"),
+          sql`${agentWakeupRequests.payload} ->> 'issueId' = ${issueId}`,
+        ),
+      )
+      .limit(1)
+      .then((rows) => Boolean(rows[0]));
+  }
+
   async function enqueueStrandedIssueRecovery(input: {
     issueId: string;
     agentId: string;
@@ -1604,6 +1619,11 @@ export function recoveryService(db: Db, deps: { enqueueWakeup: RecoveryWakeup })
 
       if (issue.status === "todo") {
         if (!latestRun) {
+          if (await hasQueuedIssueWake(issue.companyId, issue.id)) {
+            result.skipped += 1;
+            continue;
+          }
+
           if (await isInvocationBudgetBlocked(issue, agentId)) {
             result.skipped += 1;
             continue;