hey, i had the same problem about a week ago, it seems to me that aim and ichat are picky as to when they decide to let you send files, sometimes we were able to get the files sent and others no matter what it wouldnt, however i recommend restarting both computers and then trying seen as that cleared the problem at least twice for me....good luck and hopefully we can find so reason why files cant be sent easily...perhaps because im using the beta version of ichat 2.1??