I know you can ftp files to the server and have it grab them that way. Honestly I think that without resume support, and everything that has download resume support doesnt' neccesarily have upload resume support, its quite costly.
Having the encrypted filenames may be part of it? Its the only thing I can think of to cause complexity.
http://www.cyborgcow.net/info.php shows a max upload of 200MB.. do you happen to have any outgoing firewalls that may be weird?
I also could have broke it when I did the database backup right as I was logging off. I could have interrupted it. sorry!!
but I'm going to bed and server vitals looks fabulous... if not you can upload it via ftp and it'll grab it... just gotta make an ftp account for that. ftp upload has resume