@delroth I tried uploading some crops to the site and it didn't return anything, on PC it says the file is not a PNG. It turns out my crops were saved as a separate JPEG and with a different name (IMG_* instead of Screenshot_*)
I'm using CrDroid, which I just realized is LineageOS based, so that might be it.
@instereo256 note this only happens with Google's markup screenshot editor, not what crDroid ships (I am ALSO using crDroid, if that matters)