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I'm setting up a network for a small business with two geographic sites, which will be run on OS X Server.

We need a "chat" tool of some sort, and the contents of those chats could possibly contain sensitive data we can't store on someone else's servers.

Does Apple's Messages app for OS X (Mountain Lion or greater) and iOS fit the bill? I've never set up something like this before, so I'm not sure if every message sent/received via Messages app hits Apple's servers at some point.

If Messages isn't a good fit, please suggest possible alternatives which would work across Mac & iPad?

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You have a couple of options using native Apple tools:

Apple's iMessage service utilizes free iCloud accounts. The service works with the Messages app (both on Mountain Lion & iOS). All messages are routed through Apple's servers. Certificate-based encryption is used, but Apple does not document its exact nature or whether the messages get unencrypted on their servers. Here are some resources that might be helpful for looking more into this option:

OS X Server also has a Messages service that can be turned on. This creates an in-house messaging service based on the Jabber/XMPP protocol. It is by definition secure, as it routes through your in-house server. It works natively with Messages and/or iChat on the Mac (depending on OS X version) and works with a variety of apps available on the App Store. This is the way to go if you are seriously concerned about security of your conversations.

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