diff --git a/changelog.d/14649.misc b/changelog.d/14649.misc
new file mode 100644
index 0000000000..f9bfc581ad
--- /dev/null
+++ b/changelog.d/14649.misc
@@ -0,0 +1 @@
+Prune user's old devices on login if they have too many.
diff --git a/synapse/handlers/device.py b/synapse/handlers/device.py
index 7674c187ef..c935c7be90 100644
--- a/synapse/handlers/device.py
+++ b/synapse/handlers/device.py
@@ -458,10 +458,12 @@ class DeviceHandler(DeviceWorkerHandler):
 
     async def _prune_too_many_devices(self, user_id: str) -> None:
         """Delete any excess old devices this user may have."""
-        device_ids = await self.store.check_too_many_devices_for_user(user_id)
+        device_ids = await self.store.check_too_many_devices_for_user(user_id, 100)
         if not device_ids:
             return
 
+        logger.info("Pruning %d old devices for user %s", len(device_ids), user_id)
+
         # We don't want to block and try and delete tonnes of devices at once,
         # so we cap the number of devices we delete synchronously.
         first_batch, remaining_device_ids = device_ids[:10], device_ids[10:]
diff --git a/synapse/storage/databases/main/devices.py b/synapse/storage/databases/main/devices.py
index 08ccd46a2b..95d4c0622d 100644
--- a/synapse/storage/databases/main/devices.py
+++ b/synapse/storage/databases/main/devices.py
@@ -1569,11 +1569,15 @@ class DeviceBackgroundUpdateStore(SQLBaseStore):
 
         return rows
 
-    async def check_too_many_devices_for_user(self, user_id: str) -> List[str]:
+    async def check_too_many_devices_for_user(
+        self, user_id: str, limit: int
+    ) -> List[str]:
         """Check if the user has a lot of devices, and if so return the set of
         devices we can prune.
 
         This does *not* return hidden devices or devices with E2E keys.
+
+        Returns at most `limit` number of devices, ordered by last seen.
         """
 
         num_devices = await self.db_pool.simple_select_one_onecol(
@@ -1614,7 +1618,7 @@ class DeviceBackgroundUpdateStore(SQLBaseStore):
 
         # Now fetch the devices to delete.
         sql = """
-            SELECT DISTINCT device_id FROM devices
+            SELECT device_id FROM devices
             LEFT JOIN e2e_device_keys_json USING (user_id, device_id)
             WHERE
                 user_id = ?
@@ -1622,12 +1626,13 @@ class DeviceBackgroundUpdateStore(SQLBaseStore):
                 AND last_seen < ?
                 AND key_json IS NULL
             ORDER BY last_seen
+            LIMIT ?
         """
 
         def check_too_many_devices_for_user_txn(
             txn: LoggingTransaction,
         ) -> List[str]:
-            txn.execute(sql, (user_id, max_last_seen))
+            txn.execute(sql, (user_id, max_last_seen, limit))
             return [device_id for device_id, in txn]
 
         return await self.db_pool.runInteraction(
diff --git a/tests/handlers/test_device.py b/tests/handlers/test_device.py
index a456bffd63..e51cac9b33 100644
--- a/tests/handlers/test_device.py
+++ b/tests/handlers/test_device.py
@@ -20,6 +20,8 @@ from twisted.test.proto_helpers import MemoryReactor
 
 from synapse.api.errors import NotFoundError, SynapseError
 from synapse.handlers.device import MAX_DEVICE_DISPLAY_NAME_LEN, DeviceHandler
+from synapse.rest import admin
+from synapse.rest.client import account, login
 from synapse.server import HomeServer
 from synapse.util import Clock
 
@@ -30,6 +32,12 @@ user2 = "@theresa:bbb"
 
 
 class DeviceTestCase(unittest.HomeserverTestCase):
+    servlets = [
+        login.register_servlets,
+        admin.register_servlets,
+        account.register_servlets,
+    ]
+
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
         hs = self.setup_test_homeserver("server", federation_http_client=None)
         handler = hs.get_device_handler()
@@ -229,6 +237,29 @@ class DeviceTestCase(unittest.HomeserverTestCase):
             NotFoundError,
         )
 
+    def test_login_delete_old_devices(self) -> None:
+        """Delete old devices if the user already has too many."""
+
+        user_id = self.register_user("user", "pass")
+
+        # Create a bunch of devices
+        for _ in range(50):
+            self.login("user", "pass")
+            self.reactor.advance(1)
+
+        # Advance the clock for ages (as we only delete old devices)
+        self.reactor.advance(60 * 60 * 24 * 300)
+
+        # Log in again to start the pruning
+        self.login("user", "pass")
+
+        # Give the background job time to do its thing
+        self.reactor.pump([1.0] * 100)
+
+        # We should now only have the most recent device.
+        devices = self.get_success(self.handler.get_devices_by_user(user_id))
+        self.assertEqual(len(devices), 1)
+
     def _record_users(self) -> None:
         # check this works for both devices which have a recorded client_ip,
         # and those which don't.