Common mistakes in an Exchange Server 2010 migration

If you're planning an Exchange Server 2010 migration, it's best to take a holistic approach -- test, rehearse and document the upgrade -- so you don't hit any snags during the transition.

If you're planning to migrate from Exchange Server 2003 or Exchange 2007 to Exchange Server 2010, be prepared for anything. There are a few snags that you can run into.

John Bowden, CIO of Lifetime Products, a Clearfield, Utah-based lifestyle products manufacturer, was lured off Exchange Server 2007 to Exchange Server 2010 by promises of higher availability, less expensive storage and new features like text transcription for voicemail.

Like most early adopters, Bowden said he was happy he made the jump. Not only did he reach expected availability, storage and feature goals, he did so nearly pain-free. "Everything pretty much went over perfectly," Bowden said.

Indeed, Microsoft does a better job of smoothing the migration from one Exchange Server version to the next with each new implementation, said Lee Benjamin, a message architect at ExchangeGuy Consulting Services and speaker at TechTarget's Strategic Messaging: Exchange Server 2010 seminar. "It's [Microsoft has] thought ahead and pretty much well addressed most scenarios," Benjamin said.

"But let's not try to fool anyone," Benjamin added. "A migration or transition from any version to another version will have some hiccups and surprises along the way -- that's the nature of the beast." Proper planning, cautiousness and thorough testing will ensure that any slight snags encountered during the transition don't turn into pitfalls, Benjamin says.

IT administrators transitioning from Exchange Server 2003 to Exchange 2010 will likely face more problems than those upgrading from Exchange Server 2007. In moving to Exchange Server 2010, for example, Exchange Server 2003 users will finally have to bite the bullet and upgrade to the required 64-bit architecture.

While IT administrators realize this means hardware upgrades and new roles, those at larger companies must also be aware that they'll likely need to rethink message routing. This is because Active Directory sites replaced the routing groups they used in Exchange Server 2003, Benjamin said.

"Some organizations may need to put in extra hub transport servers in order to make the messages go in the route they want them to go," he said.

More on Exchange Server 2010:
New OWA features in Exchange Server 2010

Remove Exchange 2003 objects from AD to install Exchange 2010

Leapfrogging from Exchange 2003 to Exchange 2010

In the meantime, Exchange Server 2007 users shouldn't be surprised that they'll need a parallel server infrastructure for the transition, Benjamin added. Client access and hub transport 2010 servers are the only servers that can speak with the 2010 mailbox server. That means that a 2007 client access server can only talk to its 2010 counterpart, which, in turn, connects to the 2010 mailbox server.

While setting up a transitional parallel infrastructure has become standard practice for companies moving from one version of Exchange Server to another, those enterprises that have only recently moved from Exchange Server 2003 to Exchange 2007 might not appreciate juggling that process and buying new hardware so soon, Benjamin said. It's not a pitfall per say, but it's certainly an inconvenience that an IT administrator must consider for an Exchange 2010 migration.

Don't lose focus when migrating to Exchange Server 2010

"There are at least a couple of things that often turn out to be red herrings around [Exchange] migrations," said Michael Atalla, Microsoft product management director for Exchange. "However, at least in some cases, … IT administrators end up generating those, because in their heads, they've gotten what they think the primary concern or focus around a migration or upgrade should be and don't always look at the problem holistically."

For example, Atalla said some Exchange administrators focus too much moving mailbox data, which itself, is a simple operation. "Whether that migration is version to version, server to server, or server to cloud, it's often a distraction from what is necessarily a more comprehensive set of considerations," he said. "They don't ask themselves], 'Is my existing house in order?'"

"The axiom 'garbage in/garbage out' certainly applies here," he added. "If you have a client connectivity problem for your Outlook users in your existing mail environment, upgrading isn't going to make it go away and could exacerbate the situation."

Looking holistically also means thinking about third-party products for antivirus, backup, mobility, and more, Benjamin said. This is particularly important because with Exchange Server 2010, Microsoft has moved MAPI to the CAS.

"Part of supporting Exchange [Server] 2010 is [checking if] third parties have changed, fixed and tested their code since the integration is through the client access server -- as opposed to directly to the mailbox store," he sid. "You don't want to get halfway down the migration path and find out that you can't install [Exchange Server 2010] or have it stall or not work at all."

Bowden reiterated that as long as you test, rehearse and document the migration, your Exchange Server 2010 upgrade should go just fine.

Beth Schultz is an IT writer based in Chicago. You can reach her at bschultz5824@gmail.com.

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