Random Files Won't Upload to the File Manager

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We rebuilt a website to put on our own server. It is an exact copy of the old site with an additional add-on, but there is a problem. Random files won't load into the file manager. I saved them directly from the old site file manager, but when I try to load them into the new site file manager I get a server error. It shows that it is trying to upload, but never uploads. The file sizes are no different than before and I have also tried changing the names. They are also just JPEG images as well, so nothing funky about the file type either. I just don't understand how every other file we pulled from the old site worked fine, but these 6 random images didn't work. The files correspond with Real Estate listings in the Real Estate add-on, but they all come from the file manager, so that shouldn't be an issue right? It also shouldn't have anything to do with permissions or anything like that because all the other files worked. If anyone could help me out with this, it would be greatly appreciated.

rsi