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I'm trying to send a file to someone else via iChat, but it always fails. We're both using our Gmail accounts. Is it even possible with Gmail accounts? We also tried jabber accounts as well, but no luck. We both have Lion 10.7.2 and temporarily disabled the OS X firewall. Both our routers using NAT. By the way, video chats work (bad quality though) and iChat screen sharing works sometimes.

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Because it's flaky? I've never found any IM file transfer particularly reliable. – Robin Jan 29 '12 at 3:22

This link is old but may help,

I also noticed that it might help to just drag and drop the file you wish to send over the person you wish to send it to in the drop down chat menu and drop it there instead of on the chat box, it will then ask you if you want to send, click yes and it should work.

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Thanks for the reply. That advice doesn't work, as it's for a account I think. Attempting to change the port to 443 results in not being able to log on. Anyway, we used AIM accounts and it worked. I'm very surprised, but I don't think file transfers work with gmail accounts in iChat. Wow – Mark Jan 29 '12 at 1:40

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