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Is everyone else in the league able to upload fine, just this user is not?
It is somewhat tough to troubleshoot ftp upload problems since the tests I would have them do require them to know the upload account/password which most leagues wouldn't want individual managers knowing.
The only thing I can think of suggesting having them look at would be open up Game -> FTP options and making sure that the information for File upload is filled out there.
If that is filled in correctly, then something has to be preventing him from uploading. He may not be behind a firewall, but he might be running some form of personal firewall or anti-virus software. Some Anti virus software suites block FTP outbound unless it is a trusted application. Some versions of Windows might have the same set up as well where it is being blocked from within ootp.
I realize that this is not much help, but these would be the things that I would look at.
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