I figured it out, there’s a bug that I’m about to report in the plugin I’m using for plugins, it’s a doozy, but it basically comes down to you uploading multiple files with the same file name and the plugin only renaming it in one place, and it’s not the place that the approval code looks to move the images.

I have no clue how long it’ll take the plugin author to fix it on their end, so you can either start submitting files with unique names or wait until I come up with a less worse solution for submissions.