diff --git a/src/infra/outbound/delivery-queue.ts b/src/infra/outbound/delivery-queue.ts
index e0d7abcb9ee..19765e2545b 100644
--- a/src/infra/outbound/delivery-queue.ts
+++ b/src/infra/outbound/delivery-queue.ts
@@ -344,8 +344,19 @@ export async function recoverPendingDeliveries(opts: {
   for (const entry of pending) {
     const now = Date.now();
     if (now >= deadline) {
-      const deferred = pending.length - recovered - failed - skippedMaxRetries - deferredBackoff;
-      opts.log.warn(`Recovery time budget exceeded — ${deferred} entries deferred to next restart`);
+      // Increment retryCount on remaining entries so they eventually hit MAX_RETRIES
+      const remaining = pending.slice(pending.indexOf(entry));
+      for (const r of remaining) {
+        try {
+          await failDelivery(r.id, "Recovery time budget exceeded — deferred", opts.stateDir);
+        } catch {
+          /* best-effort */
+        }
+      }
+      const deferred = remaining.length;
+      opts.log.warn(
+        `Recovery time budget exceeded — ${deferred} entries deferred (retryCount incremented)`,
+      );
       break;
     }
     if (entry.retryCount >= MAX_RETRIES) {