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May 16, 2016 5:17 PM in response to nynjby AlecZ64,It's a really unfortunate limitation of Messages. The XMPP standard supports encrypted file transfer. I also don't know whether OS X server does. We should leave Apple feedback because there's no reason why file encryption support shouldn't exist.
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May 16, 2016 5:34 PM in response to AlecZ64by AlecZ64,Sorry, ignore what I said above. I misunderstood SOCKS5 and thought it provided encryption. It does not! XMPP does not support encrypted file transfer. So neither does Messages over XMPP. The only way they could do that is through some proprietary client-side protocol, which they could do (as they have done with audio/video chat)... but they haven't.
Best you can do is encrypt your files manually before you send them.
