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 d37ef118d..1c704ea21 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
@@ -20,7 +20,15 @@ const DEFAULT_MAX_DURATION_MS = 3 * 60 * 1000;
 const DIRECT_SYNC_ENV = "STACK_EXTERNAL_DB_SYNC_DIRECT";
 const POLLER_CLAIM_LIMIT_ENV = "STACK_EXTERNAL_DB_SYNC_POLL_CLAIM_LIMIT";
 const DEFAULT_POLL_CLAIM_LIMIT = 1000;
-const STALE_REQUEST_THRESHOLD_MS = 60 * 1000;
+const STALE_CLAIM_INTERVAL_MINUTES = 5;
+
+type ClaimedOutgoingRequest = OutgoingRequest & {
+  wasStale: boolean,
+};
+
+function getClaimedStaleRequestIds(claimedRequests: ClaimedOutgoingRequest[]): string[] {
+  return claimedRequests.filter((request) => request.wasStale).map((request) => request.id);
+}
 
 function parseMaxDurationMs(value: string | undefined): number {
   if (!value) return DEFAULT_MAX_DURATION_MS;
@@ -85,32 +93,63 @@ export const GET = createSmartRouteHandler({
       const startTime = performance.now();
       const maxDurationMs = parseMaxDurationMs(query.maxDurationMs);
       const pollIntervalMs = 50;
-      const staleClaimIntervalMinutes = 5;
       const pollerClaimLimit = getPollerClaimLimit();
 
       span.setAttribute("stack.external-db-sync.max-duration-ms", maxDurationMs);
       span.setAttribute("stack.external-db-sync.poll-interval-ms", pollIntervalMs);
       span.setAttribute("stack.external-db-sync.poller-claim-limit", pollerClaimLimit);
-      span.setAttribute("stack.external-db-sync.stale-claim-minutes", staleClaimIntervalMinutes);
+      span.setAttribute("stack.external-db-sync.stale-claim-minutes", STALE_CLAIM_INTERVAL_MINUTES);
 
       let totalRequestsProcessed = 0;
       let iterationCount = 0;
 
-      async function claimPendingRequests(): Promise<OutgoingRequest[]> {
+      async function claimPendingRequests(): Promise<ClaimedOutgoingRequest[]> {
         return await traceSpan("external-db-sync.poller.claimPendingRequests", async (claimSpan) => {
-          const requests = await globalPrismaClient.$queryRaw<OutgoingRequest[]>`
-              UPDATE "OutgoingRequest"
-              SET "startedFulfillingAt" = NOW()
-              WHERE "id" IN (
-                SELECT id
-                FROM "OutgoingRequest"
-                WHERE "startedFulfillingAt" IS NULL
-                LIMIT ${pollerClaimLimit}
-                FOR UPDATE SKIP LOCKED
-              )
-              RETURNING *;
-            `;
+          const requests = await retryTransaction(globalPrismaClient, async (tx) => {
+            const claimTime = new Date();
+            const reclaimBefore = new Date(claimTime.getTime() - STALE_CLAIM_INTERVAL_MINUTES * 60 * 1000);
+
+            const candidateRequests = await tx.outgoingRequest.findMany({
+              where: {
+                OR: [
+                  { startedFulfillingAt: null },
+                  { startedFulfillingAt: { lt: reclaimBefore } },
+                ],
+              },
+              orderBy: [
+                { createdAt: "asc" },
+                { id: "asc" },
+              ],
+              take: pollerClaimLimit,
+            });
+
+            const claimedRequests: ClaimedOutgoingRequest[] = [];
+            for (const candidateRequest of candidateRequests) {
+              const claimResult = await tx.outgoingRequest.updateMany({
+                where: {
+                  id: candidateRequest.id,
+                  startedFulfillingAt: candidateRequest.startedFulfillingAt,
+                },
+                data: {
+                  startedFulfillingAt: claimTime,
+                },
+              });
+
+              if (claimResult.count !== 1) {
+                continue;
+              }
+
+              claimedRequests.push({
+                ...candidateRequest,
+                startedFulfillingAt: claimTime,
+                wasStale: candidateRequest.startedFulfillingAt != null,
+              });
+            }
+
+            return claimedRequests;
+          }, { level: "serializable" });
           claimSpan.setAttribute("stack.external-db-sync.claimed-count", requests.length);
+          claimSpan.setAttribute("stack.external-db-sync.claimed-stale-count", getClaimedStaleRequestIds(requests).length);
           return requests;
         });
       }
@@ -127,6 +166,7 @@ export const GET = createSmartRouteHandler({
           await tx.outgoingRequest.deleteMany({ where: { id: { in: ids } } });
         });
       }
+
       async function processRequest(request: OutgoingRequest): Promise<void> {
         // Prisma JsonValue doesn't carry a precise shape for this JSON blob.
         const options = request.qstashOptions as any;
@@ -243,25 +283,16 @@ export const GET = createSmartRouteHandler({
             return { stopReason: "disabled", processed: 0 };
           }
 
-          const staleRequests = await globalPrismaClient.$queryRaw<{ id: string, startedFulfillingAt: Date }[]>`
-            SELECT "id", "startedFulfillingAt"
-            FROM "OutgoingRequest"
-            WHERE "startedFulfillingAt" IS NOT NULL
-              AND "startedFulfillingAt" < NOW() - ${STALE_REQUEST_THRESHOLD_MS} * INTERVAL '1 millisecond'
-            LIMIT 10
-          `;
-          iterationSpan.setAttribute("stack.external-db-sync.stale-count", staleRequests.length);
-          if (staleRequests.length > 0) {
-            captureError(
-              "poller-stale-outgoing-requests",
-              new StackAssertionError(
-                `Found ${staleRequests.length} outgoing request(s) with startedFulfillingAt older than ${STALE_REQUEST_THRESHOLD_MS}ms`,
-                { staleRequestIds: staleRequests.map(r => r.id) },
-              ),
+          const pendingRequests = await claimPendingRequests();
+          const reclaimedStaleRequestIds = getClaimedStaleRequestIds(pendingRequests);
+          iterationSpan.setAttribute("stack.external-db-sync.reclaimed-count", reclaimedStaleRequestIds.length);
+          iterationSpan.setAttribute("stack.external-db-sync.stale-count", reclaimedStaleRequestIds.length);
+          if (reclaimedStaleRequestIds.length > 0) {
+            console.warn(
+              `[Poller] Reclaimed ${reclaimedStaleRequestIds.length} stale outgoing request(s) older than ${STALE_CLAIM_INTERVAL_MINUTES} minutes.`,
+              { staleRequestIds: reclaimedStaleRequestIds },
             );
           }
-
-          const pendingRequests = await claimPendingRequests();
           iterationSpan.setAttribute("stack.external-db-sync.pending-count", pendingRequests.length);
 
           const processed = await processRequests(pendingRequests);
@@ -289,3 +320,25 @@ export const GET = createSmartRouteHandler({
     });
   },
 });
+
+import.meta.vitest?.describe("getClaimedStaleRequestIds(...)", () => {
+  import.meta.vitest?.test("returns only requests reclaimed from stale claims", ({ expect }) => {
+    expect(getClaimedStaleRequestIds([
+      {
+        id: "fresh-claim",
+        wasStale: false,
+      } as ClaimedOutgoingRequest,
+      {
+        id: "reclaimed-stale-1",
+        wasStale: true,
+      } as ClaimedOutgoingRequest,
+      {
+        id: "reclaimed-stale-2",
+        wasStale: true,
+      } as ClaimedOutgoingRequest,
+    ])).toEqual([
+      "reclaimed-stale-1",
+      "reclaimed-stale-2",
+    ]);
+  });
+});