Author: Garrett Hyder. Hello,
Another team member shared their .jpg file with me through a task, downloading it and placing onto Wordpress I realized it was 404ing. I finally narrowed this down to permissions. It seems bitrix sets the permissions of the file on download to 604 which makes it not viewable online. I had to update the permissions to 644 before it showed up.
Would love it if bitrix didn't mess with permissions or at least kept them at 644