Outlook, can you hear me? Can you feel me near you?

Might be showing my age and/or taste in music with that particular title (and if you’re totally confused by it, check out This YouTube video), but I think that it’s a great way to describe an annoyance that can happen if you’re using versions of Outlook before Outlook 2007.  Since a large portion of the users of Office are on the 2003 version (and many even earlier than that), resolution to a new server in the event of a disaster recovery event is a subject that is just as confusing as the famous rock opera I’m making use of in my title today.

When Outlook 2007 was introduced to the world with Exchange 2007, a lot was made (and rightfully so) of the new AutoDiscover features that this platform brought into the Enterprise Email marketplace.  The long and short of the AutoDiscover solution set is this:

When an Outlook 2007 client cannot find its home server – either because it is a brand new install of Outlook or because the home server has moved or been replaced – the Exchange 2007 AutoDiscover system can help Outlook 2007 find its home.  If the Outlook client can see an Exchange Server (or be directed to one by Active Directory), the Server can tell Outlook where the mailbox information for the user’s profile exists, and direct Outlook to connect to the appropriate CAS or Mailbox systems and get connected.  All the user/Admin has to do is tell Outlook the user’s email address and password, and AD with Exchange 2007 will handle it from there.  So if you’re installing Outlook for the first time, you don’t have to manually configure the Profile anymore – a great boon to Admins everywhere.

This system also kicks in if you perform Database Portability during a disaster, and have replicated the database with SCR; or have used a 3rd party disaster recovery/availability solution (see disclaimer below for all my bias information on that one =).  Once the Exchange system is responding again, AD can ferry the Outlook 2007 client to the new home for that mailbox, requiring only that the end-user close and reopen Outlook to complete the process.

However, what many folks do not realize right off the bat is that this solution set is ONLY available if you have both Outlook 2007 and Exchange 2007 as your messaging platform.  All users who need to take advantage of AutoDiscover must be using that combination of tools, and no other.  As you might expect, POP3 and IMAP systems do not AutoDiscover, but the majority of my clients were unaware that Outlook 2003 and earlier also cannot take advantage of this system, even if you have upgraded to Exchange 2007 as the messaging platform of choice.  It’s also worth noting that AutoDiscover doesn’t officially work in Exchange 2003 – no matter what Outlook version you are on.  Before I get blasted by mail on this one, I know some folks have sometimes seen it to work on Outlook 2003 with Exchange 2007, but it bombs more than it works, and officially it’s not supported.  For proof, I direct you to this article by the MS Exchange Team.

Since the code to perform AutoDiscover wasn’t in Outlook 2003, users on that client software will not be able to dynamically re-link to the new Exchange server unless the original mailbox server is still responding.  If it is, then Outlook can find the new server via the original server and re-home itself.  If not, Outlook must be manually re-directed to the new server.

Of course, there are ways around this.  You could update DNS to re-direct anyone calling for “Server 1” to the IP Address of “Server 2” – effectively re-routing all client software including POP and IMAP.  Outlook 2003 will still need to be re-profiled unless you take over the Service Principle Name (SPN) of “Server 1” on “Server 2,” but it will be a smoother transition.  Using a 3rd party tool (see disclaimer below) you may have the option of automated DNS and SPN updates, which will allow even legacy Outlook clients to jump to the new server with no more intervention than is required on Outlook 2007 with Exchange 2007 – even if you’re whole system in on the 2003 versions of those software platforms or earlier.

So, you are not without lots of options if you have any legacy servers and/or clients – or non MAPI clients – in your environment. You just need to be aware that the Exchange 2007/Outlook 2007 solutions for AutoDiscover services are not backward compatible, and plan accordingly.  Right now it looks like Exchange 2010 will have AutoDiscover that is backward compatible to Outlook 2007 only, so this soon-to-be-released platform is not going to solve this particular problem unless you’re planning on upgrading everything else in the environment to at least Outlook 2007 first.

Since I like to let folks continue to discover on their own, here’s a link to the White Paper from MSFT on AutoDiscover.

Finally, Update Roll-Up 8 for Exchange 2007 is out there, which can make life easier if you’re doing a fresh install of Exchange 2007 and want to get up to date with patches and fixes post SP1 quickly.  You can get it at this link.