diff --git a/telethon/client/messageparse.py b/telethon/client/messageparse.py
index 5f3c95c9..d7e6423e 100644
--- a/telethon/client/messageparse.py
+++ b/telethon/client/messageparse.py
@@ -164,7 +164,7 @@ class MessageParseMethods:
             mapping = sched_to_message
             opposite = id_to_message  # scheduled may be treated as normal, though
 
-        random_id = request if isinstance(request, int) else request.random_id
+        random_id = request if isinstance(request, (int, list)) else request.random_id
         if not utils.is_list_like(random_id):
             msg = mapping.get(random_to_id.get(random_id))
             if not msg:
diff --git a/telethon/client/uploads.py b/telethon/client/uploads.py
index accda7f9..ad181261 100644
--- a/telethon/client/uploads.py
+++ b/telethon/client/uploads.py
@@ -395,25 +395,18 @@ class UploadMethods:
                 fm,
                 message=caption,
                 entities=msg_entities
+                # random_id is autogenerated
             ))
 
         # Now we can construct the multi-media request
-        result = await self(functions.messages.SendMultiMediaRequest(
+        request = functions.messages.SendMultiMediaRequest(
             entity, reply_to_msg_id=reply_to, multi_media=media,
             silent=silent, schedule_date=schedule
-        ))
+        )
+        result = await self(request)
 
-        # We never sent a `random_id` for the messages that resulted from
-        # the request so we can't pair them up with the `Updates` that we
-        # get from Telegram. However, the sent messages have a photo and
-        # the photo IDs match with those we did send.
-        #
-        # Updates -> {_: message}
-        messages = self._get_response_message(None, result, entity)
-        # {_: message} -> {photo ID: message}
-        messages = {m.photo.id: m for m in messages.values()}
-        # Sent photo IDs -> messages
-        return [messages[m.media.id.id] for m in media]
+        random_ids = [m.random_id for m in media]
+        return self._get_response_message(random_ids, result, entity)
 
     async def upload_file(
             self: 'TelegramClient',