Cannot upload multiple files during issues ticket creation

Every time I try to upload +1 attachment it overwrites the previous one.
After ticket creation same issue. 1 modal window to describe what I am uploading and the file always gets overwritten with the 2nd one.

Is this a feature which forces devs to describe each attachment being uploaded?

Would love to be able to dump a bunch of files in and just use a keyword or hashtag to reference them vs this manual 1 by 1 process.