Hey Jerry,
it's much time that I don't send files via Skype so I'll try to guess and to remember the past... :D Try to go with ctrl+2 from within Skype, and see if there is the chat with the receiver in the conversations list, and do like you want to send him an instant message. You then should be able to find the infos about the transfer by pressing alt+1. If you don't see the conversation on the list or the files info, that means that for whatever reason the send did not start correctly so we'll need to test this out.
Bye!
Barbuz
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