Yahoo Messenger

I'm not sure that cross-platform file transfer works through Yahoo Messenger (it never has for me). You're better off using another method.
 
Fie transfer from Mac to PC has always worked. From time to time it worked sporadically the other way. Yahoo messenger has been updated recently, so it shouldn't currently be an issue. Check for the latest version. If it is still an issue, try a freeware alternative such as Adium for Instant Messaging.
 
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