Try it yourself! I've properly set up. Here are links:
See how the second one doesn't work? Part of HTTPS involves ensuring that the server you're talking to is who it is supposed to be, but since Google doesn't have a setonhill.edu certificate, it can't prove that it's gmail.setonhill.edu. Makes sense, right? Well, the end result is that users see their Gmail coming from mail.google.com instead of our domain.
It's not a huge problem, but it can be solved.
We use ZenDesk as our helpdesk management system and they offer the ability to do exactly this. They'll let you upload a certificate that they can then use to show clients that they're an authenticated host on your domain (link). Because of the extra cost, we haven't implemented this with ZenDesk, but this seems like a really great feature to have on a Google Apps domain. I think it'd help settle some of those subconscious fears to see a familiar setonhill.edu address instead of Google's.
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