Ah, upgrades and migrations. Nothing every happens the same way it does in the lab! First off though, I do have to say that my upgrade/migration from Exchange 2003 to Exchange 2010 SP1 was successful and relatively transparent to my end users. Of course, we have a pretty small office and only one server, so there were not a lot of moving parts.

1. It assumes you are installing the various Exchange server roles on different machines or at different times. Since I was using the “typical” installation process my CAS, Hub and Mailbox roles were being installed together.
2. You must check off the completed steps in order. Sure, you can skip around and follow the instructions however you want, but if you like crossing things off a list as you go along and something early in the list is delayed, you can’t check of any of the later tasks. For example, “Adding digital certificates on the CAS” is something that is listed very early in the checklist. I had to wait several days for my new SAN certificate to be issued but that didn’t prevent me from moving forward with my migration. However, I couldn’t play along with with the checklist.

These are small gripes and if you are a stickler for documentation, you can print, email or copy/paste the instructions from the deployment assistant into your own project plan.

In the lab, the typical installation went along with out a hitch. However, I was not blessed with such luck in production. The CAS and Hub Transport roles installed fine, but the installation choked on the Mailbox role with the following error.

Couldn’t resolve the user or group “mydomain.local/Microsoft Exchange Security Groups/Discovery Management.” If the user or group is a foreign forest principal, you must have either a two-way trust or an outgoing trust.
I found the solution in several places, but it was very nicely documented here on Peter Schmidt’s blog.

Just to clarify, you are deleting the “DiscoverySearchMailbox” user from Active Directory, rerunning your install for the mailbox role and then rerunning “setup /prepareAD” to recreate the user you deleted. Interestingly, I can’t see the Discovery Search Mailbox in my Recipient Configuration in production, but I can in my test lab. (Odd… maybe one day I’ll figure that out.)

At this point, Exchange 2010 is humming along right next my Exchange 2003 server and everything is happy and still working the way it did before, mostly because we have a Barracuda appliance that collects our inbound mail and delivers it to the Exchange 2003 server, so really nothing had changed.

I created a Receive Connector for the Barracuda, updated the Barracuda to deliver mail the Exchange 2010 server, then created my new Send Connector as per the Deployment Assistant and removed the Send Connector on the Exchange 2003 server.  Once I verified that inbound and outbound mail was still flowing it was time to take a breather and regroup for the next round.

Coming up – Getting BlackBerry BES to work again, fixing certificate errors with Outlook 2007, creating an external relay for some legacy devices on my network and figuring out why I couldn’t mount an new database after I created it.  Stay tuned.

I started this week and hopefully I’ll get to spend more time next week working on my lab for migrating from Exchange 2003 to Exchange 2010.   Today I’m using the Exchange Server Deployment Assistant, which asks a few questions about your environment and then generates a checklist of things for you to check and do as you move through the installation process.

I’m also hoping to find some time to run the Exchange Pre-Deployment Analyzer in my production environment and see if that give me some good news.

Happy Friday Everyone!

Yesterday, I spent the morning at an event hosted by Quickstart, EMC and ExtraTeam on Exchange 2010 and Unified Communications.  Not only did they have a great breakfast laid out for those of us who attended event, I picked up a few tidbits about the new versions of these Microsoft products.  The Exchange portion of morning was lead by Mike Sneeringer, who is currently the only person in the world holding both the Microsoft Certified Master in Exchange 2010 and Office Communications Server 2007 – very cool.

If you are an Exchange administrator, you’ll appreciate some of these features:

• Role Based Access Control – enables administrators to delegate permissions to responsible users based on job function without giving them access to the entire Exchange management interface. Tasks such as performing multi-mailbox searches no longer have to be the sole responsibility of Exchange Admins, allowing your organization take better advantage of features like legal hold and mailbox searches without involving the IT department.
• Multi-Mailbox Search – allows designated users (like a legal team) a web-based tool for searching across mulitple mailboxes.  This applies to online archive as well as the main mailbox.
• Legal Hold – A legal hold preserves deleted mailbox items and records changes made to mailbox items. Deleted and changed items are returned in a discovery search.
• Improved Transport Rules – will allow for greater control of how mail flows both within your organization and to outside contacts.
• Online Mailbox Moves – this is available for 2007 to 2010 migrations only, but will allow users access to their mailboxes during migration from one database to another. For migrations from 2003 mailboxes must be taken offine.

In addition to some great improvement from the mail administration side, end users will appreciate some of these improvements:

• Delivery reports – provides access to message delivery information for both end users and administrators to help answer questions common questions about mail status.  Great for offices that have multiple locations and multiple email servers.
• MailTips – I can’t describe how helpful mail tips can be any better than this blog post by the Microsoft Exchange team. You’ll never accidentally “reply to all” for an email you where were BCC’d again.
• Online Archive – Instead of using PSTs to store archive mail, users can take advantage of an online archive separate from their regular mailbox.  With SP1, that archive can even be stored in a different database.
• List Moderation – Allow designated moderators to approve messages before they are sent out to common distribution lists.  This combined with MailTips will probably reduce a lot of common interoffice email mistakes!

I’ve spent a few years running a small Exchange 2003 organization and now’s the time to start thinking about upgrading. At one point I was deciding between Exchange 2007 and Exchange 2010, but with improvements slated for Service Pack 1 for Exchange 2010, I’m sold. Granted, SP1 isn’t out for general release yet, but I’m willing to wait on my upgrade until it is. Here are some of the killer features for me:

Personal Archives – Introduced in the RTM of Exchange 2010, the personal archives act as an alternate location for users to store mail outside of the main mailbox. Service Pack 1 introduces the option to store the archive in a different database than the main mailbox, finally bringing home the chance for users to store ALL their mail on the server, without affecting the time needed to restore their main mailbox in a recovery scenario.

PST Import – One you are using that personal archive option for users, its possible to put back all that mail that users have already moved out to PST files. The import tool helps streamline this process.

Better Discovery – Improved multi-mailbox search features and search “preview” options will provide a basic “e-discovery” solution for companies that aren’t quite ready to invest in a full blown archiving and discovery product.

I’m looking forward to SP1 for Exchange 2010 as the chance to to bring some new and valuable features to our existing mail infrastructure and take the leap from Exchange 2003. A day where I don’t have to help users keep track of PST files is a day I’ll be breaking out the champagne.

Contrary to this is everyone’s need to keep every scrap of every email message. This has lead to numerous PST files created as archives for all this mail. It’s pretty safe for me to assume that almost every employee has at least one PST file and they are all stored on the network shares.(Yes, I know PST storage on the network is unsupported.) My quick search yielded about 30 GB of PST files and I know I didn’t find them all.

I would like to have a proper email archiving system that would automatically move mail from the active mailboxes to secondary storage, thus leaving my primary database small while allowing users to seamlessly access old messages. Personally, I don’t keep much in the way of work email and I think that if my company wants me to keep mail for historical purposes, they should provide an easy way to do so. However, I haven’t managed to convince the powers-that-be that this is something to embrace quite yet.