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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When Apple designed its directory service, simplicity was the likely the central focus. Open Directory is easy to configure and easy to administer, when it is working. Apple’s Open Directory quickly became the single most frustrating point of my research. Although Apple has created Open Directory from the solid foundation of Kerberos and OpenLDAP, they made a mistake at some point. I have been working on these issues for almost a year now, and I frequently ran into them while I was consulting for another Mac IT firm in Seattle. During this consulting stint that lasted for 6 months I completed over twenty OS X server installations had had direct access to resources at Apple to solve problems and report bugs. The issues that I ran into with Open Directory were ignored and denied by Apple. The stock answers that I continually received never addressed the problem.

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