Outlook Anywhere Bug with Windows Server 2008

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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Mac OS X Server 10.5 Open Directory Integration with Active Directory

AD/OD ThumbWell, 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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D5: Steve Jobs and Bill Gates Together

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

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Windows XP Life-Cycle

I’ve been running Windows Vista for over 6 months now, and I have to report that overall I think it is a great product. Microsoft has already sold over 20 million copies of Vista in just a couple months and it is looking like sales are going to keep moving forward at a steady pace.

With Apple’s anti-Vista campaign and much of the negative media about Vista, it can be hard for most people to make a decision as to how they feel about Microsoft’s latest OS. The only way to make this decision though is to just test it for yourself. Vista brings with it a whole host of new features that increase end-user satisfaction and ease IT administration, and Microsoft is going to make sure this time around that people realize this as quickly as possible.

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Upgrade from Exchange 2007 Beta 2 to RTM

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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Apple Mac OS X Server 10.4.9 Update

Apple finally released their 10.4.9 update today after about 4 or 5 developer releases. I’m currently downloading these updates onto my local software update server to deploy to my Apple servers and workstations. I’ll be looking forward to testing the previous authentication problems that I have had in the past, but I can already see a number of other outstanding issues in the list below have finally been addressed by Apple.

This is Apple’s list of fixes for Server:

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Non-domain Joined Outlook/Exchange Users

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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Accessing Exchange from Mac OS X

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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Microsoft TechNet

Microsoft TechNet is Microsoft’s information technology professional service.  In my experience TechNet has done an excellent job of just “being there” when it comes to most support and testing issues. TechNet is a Microsoft service for IT Professionals that can be purchased at a few different levels. TechNet Plus Direct is the least expensive level, at $350 a year, and with it comes many useful features:

  1. Direct download access to all Microsoft products
  2. 2 free professional support incidents
  3. 24×7 Online Concierge
  4. Microsoft TechNet user forum
  5. Subscribution to TechNet Magazine
  6. Access to e-Learning courses to help prep for MS Certification Exams
  7. Access to Beta software

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Exchange 2007 and SSL Certificates

VaultSecurity 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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Microsoft Exchange Activesync with Direct Push

There are many reasons why I love Microsoft Exchange, but Exchange Activesync with Direct Push is possibly my favorite feature. Microsoft Exchange Activesync was introduced with Exchange 2003 and for the first time Windows CE devices were able to synchronize directly with an Exchange server. Before Microsoft Activesync some form of middleware was required to have mobile phones sync with Exchange, and most notably RIM’s Blackberry Enterprise Server was the way to achieve this, but only with Blackberry devices.

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Transitioning from Exchange 2000/2003 to 2007

If you want to move your organizations 2000/2003 Exchange Server to 2007 then you’ll have to read up on Microsoft’s transition process. This is pretty much the method for moving to Exchange 2007. Part of the beauty in Exchange 2007’s separate roles is that Exchange 2000/2003 and 2007 can be installed in coexistence. Once an organization has both an Exchange 2007 and Exchange 2000/2003 server installed on the same domain, it is fairly straightforward to move the mailboxes between the two servers in the same forest.

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Migrating from IMAP to Exchange 2007

With Exchange 2003 and Small Business Server 2003 moving from IMAP to Exchange used to be fairly simple task. With Exchange 2007 though, Microsoft left out the Exchange Migration Tool that had the capabilities of downloading IMAP folders directly into the Exchange Mailboxes. Fortunately enough for those of us that want to move from IMAP to Exchange 2007 we still have options left because of Exchange 2003’s Migration Tool. Microsoft may add a migration tool into Exchange 2007 with SP1/2, but it is looking like they may never get around to adding IMAP because of the vast amount of other features being added into Exchange.

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Migrating from Exchange 5.5 to 2007

I still run across businesses every few months that to my amazement are running Exchange 5.5 even though it was released almost 10 years ago in November of 1997. For these businesses I cannot think of a better way to celebrate their mail servers 10th anniversary than throwing it in the dumpster out back. Honestly though, if your business is still running Exchange 5.5 it is time to upgrade for many reasons including:

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Microsoft Exchange Server 2007 Overview

September 28, 2003 was a great day for the Windows IT world. With the introduction of Exchange Server 2003, Microsoft had released one of their finest and most widely accepted server products to date. Exchange 2003 through its two service packs brought us some amazing features such as the Intelligent Message Filter and Direct Push email that have changed the way the corporate world is able to collaborate and communicate.

December 24, 2006 was an even more exciting day for many IT administrators that had been eagerly awaiting the introduction of Exchange Server 2007. On this special day in December, Microsoft released Exchange 2007 to manufacturing as well as to the IT community through their TechNet program.

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Microsoft Small Business Server 2003 R2

Purchasing a server as a small business can often be a daunting task, and it is one that most business will hopefully be able to view their IT Consultant as a partner and trust their decision. The factors for a Small Business to use when evaluating a server fall into four main categories; labor cost, hardware/software cost, features, and stability.

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AD/OD Integration with Mac OS X 10.4.8

There are many reasons for why a company would want to integrate an Apple Open Directory server with a Microsoft Active Directory server, but the most common scenario is that a company already has a Windows centric IT environment. In this post we will explore this scenario along with an Apple centric environment that is looking to have full featured Windows client support and greater stability.

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The Apple IMAP Experience

There are a lot of places to start when discussing IMAP email. I could start with its technical aspects, postives, negatives, supported platforms, etc. I think that it makes the most sense to start by discussing IMAP’s history.

IMAP was originally conceived at Stanford in 1986 by Mark Crispin who was later hired by the University of Washington in 1989. The first IMAP server was deployed at Stanford for testing in 1987, but it wasn’t until 1992 that the first IMAP server was truly implemented. In 1992 with the help of Mark Crispin and many others contributing to the UW-IMAP server application, the University of Washington rolled out one of the largest IMAP implementations to date using the IMAP2bis protocol, along with the Pine 2.0 front-end client application. It was during this same year, 1992, that Carnegie Mellon University began development of their own Cyrus IMAP project which is the mostly widely used IMAP service today. It was at the University of Washington in 1996 that together with vendors such as Sun and Netscape, the current IMAP4rev1 protocols specifications were completed.

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Open Directory Issues

Workgroup ManagerWhen 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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Open Directory Architecture

Open Directory is Apple’s answer to Microsoft’s enterprise directory standard, Active Directory. Open Directory is the directory service and network authentication architecture at the core of Mac OS X Server starting with OS X Server 10.3 “Panther”. As with most of Apple’s technologies Open Directory is based on an open source technology, OpenLDAP, as well as its primary authentication protocol, Kerberos, which is borrowed from MIT’s Kerberos project

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Mac OS X History

NeXT LogoAs a company, Apple has a very long history but Mac OS X’s history is actually more closely tied to its current CEO, Steven P. Jobs. Although Steve Jobs founded Apple Computers, now Apple Inc., with his friend Steve “Woz” Wozniak, he was demoted from his executive position on May 31, 1985 and then resigned on September 13, 1985. During his time away he formed a company by the name of NeXT Inc. Steve Jobs’ new company was in business from 1985 until December 20, 1996 when it was bought out by Apple.

The seed was planted for Mac OS X’s birth in 1985 when Steve Jobs met with Paul Berg, a Nobel Laureate and biochemist from Stanford, at an event held in Silicon Valley. Berg complained to Jobs about the of expense in teaching students about recombinant DNA from textbooks instead of in the wet lab. Berg explained to Jobs that he needed Apple to create something similar to a 3M workstation, due to the fact that they had more than 1MB of RAM, a megapixel display and over a megaflop of performance.

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Apple Mac OS X Server 10.4 Overview

An incredible product for businesses looking into purchasing a server on a budget. The biggest difference between Mac OS X Server and its competitors is the licensing model Apple has chosen to use. Mac OS X Server 10.4 offers a wallop of features at its $499 price point for 10-clients. If there is a need for greater than 10 users Apple also offers an unlimited client version that is only limited by the processing power of the server it is installed onto. My testing has revolved around the unlimited client version which will be the focus of this post, but both versions contain the exact same feature set.

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