diff --git a/apps/backend/src/app/api/latest/internal/external-db-sync/poller/route.ts b/apps/backend/src/app/api/latest/internal/external-db-sync/poller/route.ts
index e78b0c9ea..dfcd36941 100644
--- a/apps/backend/src/app/api/latest/internal/external-db-sync/poller/route.ts
+++ b/apps/backend/src/app/api/latest/internal/external-db-sync/poller/route.ts
@@ -47,6 +47,7 @@ export const GET = createSmartRouteHandler({
     const startTime = performance.now();
     const maxDurationMs = 3 * 60 * 1000;
     const pollIntervalMs = 50;
+    const staleClaimIntervalMinutes = 5;
 
     let totalRequestsProcessed = 0;
     async function claimPendingRequests(): Promise<OutgoingRequest[]> {
@@ -58,6 +59,7 @@ export const GET = createSmartRouteHandler({
             SELECT id
             FROM "OutgoingRequest"
             WHERE "startedFulfillingAt" IS NULL
+              OR "startedFulfillingAt" < NOW() - (${staleClaimIntervalMinutes} * INTERVAL '1 minute')
             ORDER BY "createdAt"
             LIMIT 100
             FOR UPDATE SKIP LOCKED
@@ -67,11 +69,22 @@ export const GET = createSmartRouteHandler({
         return rows;
       });
     }
+    async function deleteOutgoingRequest(id: string): Promise<void> {
+      await retryTransaction(globalPrismaClient, async (tx) => {
+        await tx.outgoingRequest.delete({ where: { id } });
+      });
+    }
+    async function releaseOutgoingRequest(id: string): Promise<void> {
+      await retryTransaction(globalPrismaClient, async (tx) => {
+        await tx.outgoingRequest.updateMany({
+          where: { id, startedFulfillingAt: { not: null } },
+          data: { startedFulfillingAt: null },
+        });
+      });
+    }
     async function processRequests(requests: OutgoingRequest[]): Promise<number> {
-      let processed = 0;
-
-      for (const request of requests) {
-        try {
+      const results = await Promise.allSettled(
+        requests.map(async (request) => {
           // Prisma JsonValue doesn't carry a precise shape for this JSON blob.
           const options = request.qstashOptions as any;
           const baseUrl = getEnvVariable("NEXT_PUBLIC_STACK_API_URL");
@@ -94,13 +107,21 @@ export const GET = createSmartRouteHandler({
             body: options.body,
           });
 
+          await deleteOutgoingRequest(request.id);
+        }),
+      );
+
+      let processed = 0;
+      for (const [index, result] of results.entries()) {
+        if (result.status === "fulfilled") {
           processed++;
-        } catch (error) {
-          captureError(
-            `poller-iteration-error`,
-            error,
-          );
+          continue;
         }
+        captureError(
+          "poller-iteration-error",
+          result.reason,
+        );
+        await releaseOutgoingRequest(requests[index].id);
       }
 
       return processed;
diff --git a/apps/e2e/tests/backend/endpoints/api/v1/external-db-sync-advanced.test.ts b/apps/e2e/tests/backend/endpoints/api/v1/external-db-sync-advanced.test.ts
index b7e39aa29..b0c6413f0 100644
--- a/apps/e2e/tests/backend/endpoints/api/v1/external-db-sync-advanced.test.ts
+++ b/apps/e2e/tests/backend/endpoints/api/v1/external-db-sync-advanced.test.ts
@@ -329,7 +329,7 @@ describe.sequential('External DB Sync - Advanced Tests', () => {
     const res = await client.query(`SELECT * FROM "users" WHERE "primary_email" = $1`, ['special@example.com']);
     expect(res.rows.length).toBe(1);
     expect(res.rows[0].display_name).toBe(specialName);
-  });
+  }, TEST_TIMEOUT);
 
   /**
    * What it does:
diff --git a/apps/e2e/tests/backend/endpoints/api/v1/external-db-sync-basics.test.ts b/apps/e2e/tests/backend/endpoints/api/v1/external-db-sync-basics.test.ts
index 3c114e675..b366a47c1 100644
--- a/apps/e2e/tests/backend/endpoints/api/v1/external-db-sync-basics.test.ts
+++ b/apps/e2e/tests/backend/endpoints/api/v1/external-db-sync-basics.test.ts
@@ -288,7 +288,7 @@ describe.sequential('External DB Sync - Basic Tests', () => {
     `);
     expect(tableCheck.rows[0].exists).toBe(true);
     await verifyInExternalDb(client, 'auto-create@example.com', 'Auto Create User');
-  });
+  }, TEST_TIMEOUT);
 
   /**
    * What it does: