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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Fortunately for Microsoft there was a lot of excitement around the prereleases of Exchange 2007 Beta 2, and many of us liked it so much more than Exchange 2003 or our previous solutions that we upgraded to it early.  Luckily for all of us who did this, Microsoft left a way for us to get our Beta 2 configuration up to RTM.

On December 24, when I wanted to move my test machine over from Beta 2 to RTM I had to make a decision. The choices were that I could format the hard drive and reinstall Windows 2003 R2 x64 and Exchange 2007 RTM, or I could just upgrade to the RTM version.  Upgrade’s are always less desirable and in this case completely unsupported by Microsoft for a production environment.  In my case though, this was just for a testing environment and I was in a hurry to get to RTM since I was tired of some of the bugs in my Beta 2 configuration.  This was the process that I used which worked well for me:

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This topic is rarely addresssed because most Outlook/Exchange users tend to be domain joined, but in my testing I ran into a few issues that are worth making a public note of. First off, I want to say that I only tested this scenario with Exchange 2007, but this may be relevant to Exchange 2003 as well.

I did not run into any issues when using Exchange 2007 with Outlook when the Exchange server was also the Domain Controller (DC) and Global Catalog (GC) server. When I separated the Exchange 2007 server and the DC/GC I ran into an issue with Outlook not authenticating properly to the Directory Service through the RPC over HTTPS proxy. I was not able to track down the full reason behind the problem, but I figured out the solution as well as contributing factors.

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Sadly, in a Windows centric environment, such as an Exchange organization, the Macs often get left behind. The Macs can play nicely with the PCs in terms of collaboration, but we can probably never expect them to have all the same features that Outlook and Exchange are capable of achieving.

On a Mac there are really only two options for accessing your Exchange mailbox, and that is an IMAP client or an OWA (Outlook Web Access) based client. Thankfully for us, most Apple computers already have both of these; Apple Mail and Microsoft Entourage. Both of these clients can interface with Exchange both over OWA or IMAP.

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Security is a huge concern when it comes to email. Email is the primary communication mechanism for many businesses and sensitive information is passed both externally and internally via email everyday. Since we cannot leave it to chance that a hacker might intercept an email, we use Secure Socket Layer (SSL) certificates to encrypt the data that is transmitted internally between servers and Transport Layer Security (TLS) to encrypt the data that is transported over SMTP traffic both internally and externally.

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