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I have an iPhone which is working with Exchange for email / calendaring over the public internet.

I have a Mac with Outlook which is working with Exchange for email / calendaring but only over a VPN connection. My IT dept tells me I cannot check email over the public internet using outlook --- this sounds very questionable since my iphone is going over the public inet without issue.

The server URL's are quite different. I tried simply entering the public URL on the Mac but it wouldn't work over the public inet or on the VPN. I'm thinking there must be some kind of discovery happening on the iphone which is telling it where to go to sync mail / calendar over the public inet.

So my question is this: does anyone know of a way to get the proper URL's for the exchange server and directory service for Outlook from an iOS device (or at least maybe determine the URL's I should use based on the URL I'm entering on the iOS device)?

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If you have a router, you can possibly sniff the traffic going to it and figure it out that way. – user3463 May 22 '12 at 20:58
I did take a peek using wireshark but unfortunately it wasn't much help. Most of the traffic is encrypted. After searching a bit it seems iOS platforms are using ActiveSync which is not supported in Desktop software -- I may just be out of luck. – jckdnk111 May 22 '12 at 21:21

(For some reason I'm not seeing the add comment links)

Which version of Outlook for Mac are you using? If it's 2011, it uses the same service as iOS devices.

About this comment "My IT dept tells me I cannot check email over the public internet using outlook" I think it sounds a bit ridiculous and very questionable to me, the iPhone access it over a public 3g network (unless the device is configured to access over VPN only)

In my company we used to have Exchange (we now moved to Google Apps), but when we had it we used a different URL for the device and another URL for the Mac.

For example in my Mac the URL was something like this

And on my iPad just the first bit

Another thing you can try in outlook if it doesn't accept the URL as an exchange server is to configure it as an IMAP or Entourage server.

Hope this helps.

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