Last fall at our Windows Connections conference in Las Vegas, Windows IT Pro held a small workshop for IT pros whose organizations were just beginning to plan their migration to Exchange Server 2010. I recently checked back in with a few attendees to see how their upgrades were going. One IT pro said his company had abandoned any immediate plans to migrate, but two others were in the thick of the transition. Pam Dudley, a systems administrator for a Nashville-based law firm, shared her insights about her organization’s reasons for the upgrade and lessons learned in the planning process.

Dudley said that the high-availability features of Exchange 2010 were hands-down the biggest driver for her company’s upgrade. “Our Exchange data has grown at such a rate that we’re really just running out of room,” Dudley said. “We’ve just gotten a new SAN up and running, and with the conversion to Exchange 2010 we’ve been charged with moving storage from local machines to the SAN. We’re also looking at virtualizing Exchange. So this one product migration has become a huge project encompassing other things.”

One of the factors affecting the Exchange migration is a new document-management system the firm implemented; this application allows workers to transfer client documents directly from Exchange. Very few documents at the law firm now exist in physical form.

In addition, IT organizations need to plan and deploy new data-retention policies as a result of new regulations such as the Health Information Technology for Economic and Clinical Health Act (HITECH), which expands the reach of the Health Insurance Portability and Accountability Act (HIPAA) to include business associates of the entities that are subject to HIPAA. “We have to keep this data secure, and we have a number of protocols to follow that we didn’t before,” Dudley said.

The Exchange upgrade has caused Dudley’s organization to reassess other initiatives and launch related projects. The company is trying to reduce hardware by removing mailboxes from physical servers and putting them on the SAN. The company’s virtualization strategy is still in the planning stage. “There is some debate at this point about exactly how much of the Exchange system we’re going to virtualize,” Dudley said. She’s also reviewing which workloads to put on the virtual machines and which to put on the physical servers.

In addition to scrutinizing their virtualization strategy, Dudley said that the rollout of Outlook 2010 will be a significant factor for the organization because of the ties to their new document- management system. “I know that with Exchange 2010, the functionality available to you is dependent on the Outlook client you use, and we’re still on Outlook 2003,” Dudley said. “The further back you go with the client—the further away you get from the current Exchange server—the more functionality you lose on that Exchange server. And of course with Outlook, we have to wait on the third-party vendors for the snap-ins so they can also work.”

The other piece of the Exchange upgrade puzzle is preparing Active Directory (AD) for the migration. Although Dudley said she’s familiar with the AD cleanup needed because of the organization’s previous migration, the current project has caused her organization to reassess its Windows Server deployment as well. Most of the firm’s servers are running Windows Server 2003, but Dudley is targeting certain machines for upgrades. “We currently have one AD server that’s on Windows Server 2008 and we’re going to move that to R2,” Dudley said. “We’re going to bring up an additional domain controller on Windows Server 2008 R2. We’ll take the other Windows Server 2003 machines out of the mix so that we have the AD forest on Windows Server 2008.”

The other rollout that will follow closely behind the Exchange 2010 migration is an upgrade to Windows 7. “But we’ve got to have 2008 to take advantage of some of the opportunities Windows 7 offers in efficiencies.”

Aside from emphasizing that many other systems will be connected to an Exchange 2010 migration, Dudley advises IT pros contemplating an upgrade to closely examine the changes in architecture between Exchange 2007 and Exchange 2010. “It will change how you allocate roles, how you allocate resources, and how you do your planning,” she said. “The parts of the new architecture that are different are very different.”

Dudley is planning to complete the upgrade to Exchange Server 2010 by the third quarter of this year. Although the migration itself will be fairly straightforward, the year clearly will be packed with challenges as she navigates the changes that the Exchange migration will cause to other systems.