404 Linking Images

I am having issues linking files (trying a pdf) with the uploading tool in the admin. I am able to upload through both the file manager and the wysiwyg on the page i am trying to edit. so the file seems to be stored.

however, when i try to link it, the browser popup doesn’t display the file i am trying to link to. if i do a search, it will show up, but not in the initial list. i then link it to that file after searching and when i check it on the front-side it brings a 404 like the file doesn’t exist. this ever happen to anyone else? as far as i know there has not been any type of config changes.