The file created is the size of the original (uploaded) file, and looking into it also reveals it’s not filled “artificially” filled with data waiting to be replaced, the file is there. Teamspeak just fails to display it in the Icon Manager or in the Server itself.
EDIT: After checking inside the file itself with a text editor, the uploaded file in the server’s files is a carbon-copy of the original file, so the issue isn’t network related, but with Teamspeak itself.
EDIT2: Reinstalling the whole of Teamspeak, Restarting the server and my computer seems to have done the trick, uploading icons now works with all files that previously didn’t, still don’t know what caused it since my TS Install was recent and the latest version
