diff --git a/litellm/accounting/worker.py b/litellm/accounting/worker.py
index 32bf24d4ba5..be18d8ac6b1 100644
--- a/litellm/accounting/worker.py
+++ b/litellm/accounting/worker.py
@@ -87,10 +87,15 @@ async def flush_accounting_deliveries(
         for _ in range(batch_size):
             if time.monotonic() >= retry_deadline or not _progressed(await run_batch(retry_only=True)):
                 break
-        await repository.cleanup_applied(
-            retention_days=int(os.environ.get("LITELLM_ACCOUNTING_DELIVERY_RETENTION_DAYS", "1")),
-            batch_size=batch_size * 2,
-        )
+        retention_days: Final = int(os.environ.get("LITELLM_ACCOUNTING_DELIVERY_RETENTION_DAYS", "1"))
+        cleanup_deadline: Final = time.monotonic() + 5
+        for _ in range(batch_size):
+            if (
+                await repository.cleanup_applied(retention_days=retention_days, batch_size=batch_size * 2)
+                < batch_size * 2
+                or time.monotonic() >= cleanup_deadline
+            ):
+                break
         metrics: Final = await repository.metrics()
         record_deliveries(metrics, time.monotonic() - started)
         if metrics.batch_count >= int(
diff --git a/tests/integration/database/test_spendlogs_ledger_parity.py b/tests/integration/database/test_spendlogs_ledger_parity.py
index 68ab76d694d..60f3c074cca 100644
--- a/tests/integration/database/test_spendlogs_ledger_parity.py
+++ b/tests/integration/database/test_spendlogs_ledger_parity.py
@@ -103,6 +103,30 @@ async def test_worker_drains_a_backlog_in_one_run_one_configured_batch_per_trans
         await client.db.disconnect()
 
 
+@pytest.mark.asyncio
+async def test_worker_removes_more_expired_receipts_than_one_cleanup_batch_in_one_run(
+    parity_database: str, monkeypatch: pytest.MonkeyPatch
+):
+    from litellm.accounting.worker import flush_accounting_deliveries
+
+    monkeypatch.setenv("DATABASE_URL", parity_database)
+    monkeypatch.setenv("LITELLM_ACCOUNTING_DELIVERY_BATCH_SIZE", "100")
+    client = PrismaClient(database_url=parity_database, proxy_logging_obj=proxy_server.proxy_logging_obj)
+    with psycopg.connect(parity_database, autocommit=True) as connection:
+        connection.execute(
+            'INSERT INTO "LiteLLM_SpendLogDelivery" (request_id, accounting_payload, is_batch, state, applied_at) '
+            "SELECT 'expired-' || n, '{}'::jsonb, false, 'applied', CURRENT_TIMESTAMP - INTERVAL '2 days' "
+            "FROM generate_series(1, 501) AS n"
+        )
+    await client.db.connect()
+    try:
+        await flush_accounting_deliveries(DBSpendUpdateWriter(), client, proxy_server.proxy_logging_obj)
+        with psycopg.connect(parity_database) as connection:
+            assert connection.execute('SELECT COUNT(*) FROM "LiteLLM_SpendLogDelivery"').fetchone() == (0,)
+    finally:
+        await client.db.disconnect()
+
+
 @pytest.mark.parametrize("ledger", [False, True])
 @pytest.mark.parametrize("exclude_messages", [False, True])
 @pytest.mark.asyncio