diff --git a/pybricksdev/ble/oad/control_point.py b/pybricksdev/ble/oad/control_point.py
index fa94fb1..6bd8016 100644
--- a/pybricksdev/ble/oad/control_point.py
+++ b/pybricksdev/ble/oad/control_point.py
@@ -6,6 +6,7 @@
 from typing import AsyncGenerator
 
 from bleak import BleakClient
+from bleak.exc import BleakError
 
 from ._common import OADReturn, SoftwareVersion, oad_uuid
 
@@ -50,7 +51,11 @@ async def __aenter__(self):
         return self
 
     async def __aexit__(self, *exc_info):
-        await self._client.stop_notify(OAD_CONTROL_POINT_CHAR_UUID)
+        try:
+            await self._client.stop_notify(OAD_CONTROL_POINT_CHAR_UUID)
+        except BleakError:
+            # ignore if already disconnected
+            pass
 
     def _notification_handler(self, sender, data):
         self._queue.put_nowait(data)
diff --git a/pybricksdev/ble/oad/image_identify.py b/pybricksdev/ble/oad/image_identify.py
index f342a01..1a12390 100644
--- a/pybricksdev/ble/oad/image_identify.py
+++ b/pybricksdev/ble/oad/image_identify.py
@@ -11,6 +11,7 @@
 import struct
 
 from bleak import BleakClient
+from bleak.exc import BleakError
 
 from ._common import ImageInfo, OADReturn, SoftwareVersion, oad_uuid
 
@@ -35,7 +36,11 @@ async def __aenter__(self):
         return self
 
     async def __aexit__(self, *exc_info):
-        await self._client.stop_notify(OAD_IMAGE_IDENTIFY_CHAR_UUID)
+        try:
+            await self._client.stop_notify(OAD_IMAGE_IDENTIFY_CHAR_UUID)
+        except BleakError:
+            # ignore if already disconnected
+            pass
 
     async def validate(
         self,
diff --git a/pybricksdev/cli/oad.py b/pybricksdev/cli/oad.py
index 7ccd96c..2123fae 100644
--- a/pybricksdev/cli/oad.py
+++ b/pybricksdev/cli/oad.py
@@ -62,10 +62,17 @@ async def flash_oad_image(firmware: BinaryIO) -> None:
         print("No OAD device found")
         return
 
+    disconnect_event = asyncio.Event()
+
+    def on_disconnect(_):
+        disconnect_event.set()
+
     # long timeout in case pairing is needed
-    async with asyncio.timeout(60), BleakClient(device) as client, OADImageIdentify(
+    async with asyncio.timeout(60), BleakClient(
+        device, on_disconnect
+    ) as client, OADImageIdentify(client) as image_identify, OADControlPoint(
         client
-    ) as image_identify, OADControlPoint(client) as control_point:
+    ) as control_point:
         image_block = OADImageBlock(client)
 
         print(f"Connected to {device.name}")
@@ -133,6 +140,10 @@ async def flash_oad_image(firmware: BinaryIO) -> None:
         await control_point.enable_oad_image()
         print("Done.")
 
+        # avoid race condition of requesting disconnect while hub is initiating
+        # disconnect itself - this can leave BlueZ in a a bad state
+        await disconnect_event.wait()
+
 
 async def dump_oad_info():
     """