diff --git a/tests/integration/_support/database_relay.py b/tests/integration/_support/database_relay.py
index 986849c3403..65cf213340c 100644
--- a/tests/integration/_support/database_relay.py
+++ b/tests/integration/_support/database_relay.py
@@ -182,12 +182,15 @@ class DroppedConnectionRelay:
         server_reader, server_writer = await asyncio.open_connection(self._upstream_host, self._upstream_port)
 
         async def forward(reader: asyncio.StreamReader, writer: asyncio.StreamWriter, inspect: bool) -> None:
+            tail = b""  # rebind-ok: carries the previous read's end so a trigger split across reads still matches
             try:
                 while chunk := await reader.read(65536):
-                    if inspect and self._armed.is_set() and self._trigger in chunk:
+                    window: Final = tail + chunk
+                    if inspect and self._armed.is_set() and self._trigger in window:
                         self.dropped.set()
                         client_writer.close()
                         return
+                    tail = window[-(len(self._trigger) - 1) :]
                     writer.write(chunk)
                     await writer.drain()
             except (ConnectionError, asyncio.IncompleteReadError):
diff --git a/tests/unit/integration_support/test_database_relay.py b/tests/unit/integration_support/test_database_relay.py
new file mode 100644
index 00000000000..a86e0fc6ca8
--- /dev/null
+++ b/tests/unit/integration_support/test_database_relay.py
@@ -0,0 +1,46 @@
+from __future__ import annotations
+
+import socket
+import socketserver
+import threading
+from collections.abc import Iterator
+from typing import Final
+from urllib.parse import urlsplit
+
+import pytest
+
+from tests.integration._support.database_relay import dropped_connection_relay
+
+TRIGGER: Final = b'SELECT "startTime" FROM "LiteLLM_SpendLogs"'
+SPLIT_AT: Final = len(TRIGGER) // 2
+
+
+class _EchoHandler(socketserver.BaseRequestHandler):
+    def handle(self) -> None:
+        while chunk := self.request.recv(65536):
+            self.request.sendall(chunk)
+
+
+@pytest.fixture
+def echo_upstream_url() -> Iterator[str]:
+    server: Final = socketserver.ThreadingTCPServer(("127.0.0.1", 0), _EchoHandler)
+    server.daemon_threads = True
+    threading.Thread(target=server.serve_forever, daemon=True).start()
+    try:
+        yield f"postgresql://relay:relay@127.0.0.1:{server.server_address[1]}/relay"
+    finally:
+        server.shutdown()
+        server.server_close()
+
+
+def test_dropped_connection_relay_trips_on_a_trigger_split_across_two_reads(echo_upstream_url: str) -> None:
+    with dropped_connection_relay(echo_upstream_url, TRIGGER) as (relay, relayed_url):
+        relay.arm()
+        port: Final = urlsplit(relayed_url).port
+        assert port is not None
+        with socket.create_connection(("127.0.0.1", port), timeout=5) as client, client.makefile("rb") as echoed:
+            client.sendall(TRIGGER[:SPLIT_AT])
+            assert echoed.read(SPLIT_AT) == TRIGGER[:SPLIT_AT]
+            client.sendall(TRIGGER[SPLIT_AT:])
+            assert relay.dropped.wait(5), "the relay never saw the trigger that arrived in two reads"
+            assert echoed.read() == b""