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Does that mean they can view private pictures sent via iMessage?

I've wondered the same thing about Dropbox. If I were to open my dropbox at work, could my employer view private things in the dropbox? Even if I don't open the file, an icon will still load in the browser view.

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If I were to open my dropbox at work, could my employer view private things in the dropbox?

If your employer has physical access or the admin password to your work computer (very likely) then anything you store or do on it is potentially compromised. (including passwords, keys, etc.) Same for work-issued phones etc. The security of the protocol is irrelevant in this case as you're trusting a compromised client.

Your employer could MITM all your SSL connections just by installing their own cert installed on the machine, so yeah.

Indeed. This is why Apple sending your AppleID and password in the clear inside the SSL connection to Apple is troubling. That makes it relatively easy for the right IT people to steal those credentials. Hopefully this will be fixed soon.

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