During my latest work transitioning a client’s Exchange environment from 2007 to 2010 I stumbled across an issue I had not ran in to previously. This issue involved running different versions of (2007 and 2010) Outlook Anywhere (OA) in one environment simultaneously. I couldn’t find good documentation on this process from Microsoft so I figured I’d hopefully help someone else out by documenting the process I went through.

First off, getting your Client Access Servers (CAS) up and running with the proper hostnames and associated SAN certificate is essential. The initial plan was to bring up the 2010 Outlook Anywhere (OA a.k.a. RPC over HTTP) and then disable the 2007 OA due to Microsoft’s recommendation to transition the CAS fully before proceeding with the migration. With this latest transition, I needed to keep both the Exchange 2007 and 2010 OA proxies running side-by-side. This was necessary due to having numerous domains that were hosted on this Exchange environment that wouldn’t be able to have their external DNS edited in time for the beginning of the migration (for a variety of reasons that are outside the scope of this post).

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I have been using Apple laptops since about 2002 when I bought my first 1GHz Titanium PowerBook G4. At the time, my needs were very small and I fell in love with Mac OS X 10.2 Jaguar. Following my TiBook, I had a couple different Aluminum PowerBook G4s and finally got my first C2D (Core 2 Duo) MBP (MacBook Pro) in November of 2006. That C2D MBP treated me very well for the last 2 years and my only real complaints with it were:
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As an IT admin it will happen to all of us at some point; there will be that problem that seems like you are 10 minutes away from fixing that quickly turns into 10 hours and then 2, 3, even 5+ days.  Before you know it, you have spent a week with nearly zero sleep and a lot of caffeine and then you finally realize that you are not any further along than when you started.  I spent the last week banging my head up against a wall trying to get a clients new Windows Server 2008 and Exchange 2007 SP1 environment up and running, only to find out that Microsoft has a crippling bug in Windows Server 2008 that won’t allow Outlook Anywhere (a.k.a. RPC over HTTP) to run in its default configuration.

The most unfortunate part about this is that Microsoft is still yet to release any information publicly about this problem, which is really sad because they generally do such a great job of at least posting limitations of their products on many of their wonderful blogs.  I had to search the Internet and eventually found articles that led me in the right direction but I was never able to find a blog/article that outlined the exact steps that I used to fix/diagnose Outlook Anywhere which is why I really felt the need to write this post.

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Well, I’ve been swamped with work for the last 10 months and haven’t even come close to having a chance to sit down and write any well thought out blog entries.  I was compelled though a couple weeks ago to write a new entry about the coolest new feature that I stumbled across in Apple’s still relatively new OS X 10.5.2 Server.

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All the videos from Steve Jobs and Bill Gates interview by Walt Mossberg and Kara Swisher at the WSJ D5 conference.

“To create a new standard, it takes something that’s not just a little bit different, it takes something that’s really new and really captures people’s imagination and the Macintosh, of all the machines I’ve ever seen, is the only one that meets that standard.” –Microsoft founder Bill Gates, 1984

“If I were running Apple, I would milk the Macintosh for all it’s worth–and get busy on the next great thing. The PC wars are over. Done. Microsoft won a long time ago.” –Steve Jobs, 1996