diff --git a/changelog.d/6363.bugfix b/changelog.d/6363.bugfix
new file mode 100644
index 000000000..d023b4918
--- /dev/null
+++ b/changelog.d/6363.bugfix
@@ -0,0 +1 @@
+Fix `to_device` stream ID getting reset every time Synapse restarts, which had the potential to cause unable to decrypt errors.
\ No newline at end of file
diff --git a/synapse/storage/data_stores/main/deviceinbox.py b/synapse/storage/data_stores/main/deviceinbox.py
index f04aad074..96cd0fb77 100644
--- a/synapse/storage/data_stores/main/deviceinbox.py
+++ b/synapse/storage/data_stores/main/deviceinbox.py
@@ -358,8 +358,21 @@ class DeviceInboxStore(DeviceInboxWorkerStore, DeviceInboxBackgroundUpdateStore)
     def _add_messages_to_local_device_inbox_txn(
         self, txn, stream_id, messages_by_user_then_device
     ):
-        sql = "UPDATE device_max_stream_id" " SET stream_id = ?" " WHERE stream_id < ?"
-        txn.execute(sql, (stream_id, stream_id))
+        # Compatible method of performing an upsert
+        sql = "SELECT stream_id FROM device_max_stream_id"
+
+        txn.execute(sql)
+        rows = txn.fetchone()
+        if rows:
+            db_stream_id = rows[0]
+            if db_stream_id < stream_id:
+                # Insert the new stream_id
+                sql = "UPDATE device_max_stream_id SET stream_id = ?"
+        else:
+            # No rows, perform an insert
+            sql = "INSERT INTO device_max_stream_id (stream_id) VALUES (?)"
+
+        txn.execute(sql, (stream_id,))
 
         local_by_user_then_device = {}
         for user_id, messages_by_device in messages_by_user_then_device.items():