Mike in Real Life

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A while ago, I purchased a Mac. I love my Mac. It beats the crap out of any Windows computer I have ever owned. I do have one problem, though, and it deals with Entourage and VPN, which may actually be something I could just blame on Microsoft.

At work, we are still using the dinosaur Exchange 2000 for our email. We have a “new” server sitting around, and when I say new I mean hardly even used because we have had it for almost a year and a half, bur out network administrator has yet to get it totally up and running. Part of the problem is his decision to move from the old 32 bit architecture to the 64 bit and the ensuing problems with upgrading from Exchange 2000 to Exchange 2007. Some day I am sure he will finally get it up and running (and he damn well better before Snow Leopard comes out in September with integrated Exchange 2007 support in Apple Mail!) but, much like what was said at the end of Conan the Barbarian, that is a story for another day. Because of this, my options are currently very limited with regards to email clients.

I could use Apple Mail or Thunderbird, but neither one of them has MAPI support, so I would be without my calendar and contacts being updated on my Blackberry. This leaves me with Entourage.

Overall, I do like Entourage. It reminds me a good deal of Outlook, only without some of the bloated crap in that particular PIM (does anyone actually use the journal?). My main gripe deals with trying to connect to our Exchange server when I am away from the office.

Entourage has built in support for OWA. One would think that, since we have OWA access, I should be able to easily connect to the server and be done without. Unfortunately, this is not the case. I get the feeling that forms login is all that is supported, and we, unfortunately, are still using pop up login. Maybe, in the near future, this could be fixed with our upgrade, but like I said, when that happens I am switching to Apple Mail.

The only other option available is to connect to the network at work via VPN and access the Exchange server that way. While this sounds good in theory, I have found that it does not work very well in practice. For some reason, when I start the VPN tunnel, Entourage refuses to connect. Every other email account works without any issues what so ever, but for some reason it refuses to find our Exchange server.

I have tried using the IP address, using the server name, using the fully qualified server name with the domain, and I get nothing. It feels almost like I picked the box on Wheel of Fish and Kuni just yelled, “Nothing! Absolutely Nothing!! STUPID!!! YOU SO STUUPPIIIDDD!!!!”

Hopefully, someone who actually knows what my problem is will stumble across this soon and perhaps, if I am truly lucky, give me some ideas about what may be causing Entourage to not like my VPN tunnel. Perhaps I have set something up that won’t allow it to connect? Maybe Entourage just hates VPN tunnels? I definitely have run out of ideas.