by Josh Arrington
As readers of our blog know, we recently crowned Thomas Deliduka as this year’s winner of Cyber-Ark’s SysAdmin Appreciation Day Twitter contest. Thomas beat out several other participants in a competitive contest by impressing the judges with his efficient and error-free Microsoft Exchange rollout for 100+ users. But since there’s only so much you can learn in 140 characters (or less) we thought it would be valuable to learn more about his “winning” achievement. Without further ado, here’s our Q&A with Thomas—we hope this not only shines some more light on the merits of his winning submission, but also provides some great insight for other SysAdmins out there who just may find themselves in a similar situation!
CyberArk: Thomas, in addition to your new title as “SysAdmin Appreciation Day Twitter Contest Winner,” could you tell us a bit about your day job?
Thomas: I am the Director of Information Technology at the Columbus Museum of Art in Columbus, Ohio. It is probably the best job I have ever had, I get all the hands-on experience but also the responsibility of a department head.
CyberArk: Although there were many great submissions and it was a tough decision for the judges, your Tweet/achievement immediately resonated with the judges and they were unanimously impressed. Can you tell us a little bit more about how you first approached the rollout?
Thomas: Once I was assigned the project in late 2010, I began researching what I actually needed to do to upgrade Exchange. At first, I just bookmarked some posts and then left it alone—it wasn’t until February when I purchased two new servers and realized I needed to start getting to work. Another resource that was helpful was this amazing blog post, which I’m not sure I could find anymore, that outlined how to run Exchange in legacy mode and then slowly move people over.
CyberArk: And then the fun began?
Thomas: I got the first server OS installed and named it “xxxxxxx-01″ because it was going to be the first server. However, then I read further and find out I needed to install the CAS server first. In my mind, the CAS server should be server 2, so before I went too much further, I renamed the server and started installing the operating system on server 1.
I got the CAS server online the first day and it immediately integrated it with my 2003 environment—including allowing for the ActiveSync calls to come first to the Exchange 2010 server and then get routed to the 2003 server through the “legacy” DNS entry.
That was almost seamless, I was so surprised. None of my phone users noticed any changes at all.
On the second day, I finished the Mailbox server—I couldn’t wait to convert my own mailbox because I always experiment on myself. So, I finished that, and again, ActiveSync connected just fine on my Android device and kept on humming.
CyberArk: Once you had tested the migration on your own accounts, how did you approach the other users?
Thomas: Right away I started moving people who I knew were on vacation and out of the office—just about 10 mailboxes or so. I found that by bringing up Outlook after the migration of the mailbox, the system automatically updated to the new Exchange Server. That was surprising, but welcome, since I knew I wouldn’t have to visit every single user!
After that, it was smooth sailing. I told people to expect a mailbox migration over the new few days and that they shouldn’t notice any changes. I connected via VPN at night over the next few days and converted about 20 or 30 mailboxes at a time. The final group to convert was the Mac Users—we were using Microsoft Entourage 2008 on about five computers. When we needed to migrate their mailboxes, Entourage would no longer work so I had to install the updated Office 2011 before migrating their mailboxes, then immediately convert and connect so they would see no downtime.
That was fine for four of the users, but there was one who decided he simply couldn’t have me messing with his computer for at least another four days. So, I migrated his mailbox and taught him how to use the new Webmail with Exchange 2010.
The day I migrated the last mailbox, I went ahead and separated the 2003 server and shut it down! From start to finish it was a little less than two weeks but it’s easier to say two weeks.
CyberArk: Any additional information you learned from all this?
Thomas: One issue you could say I had was that Microsoft doesn’t allow Domain Admins to sync e-mail through ActiveSync. There is an inherent value within Active Directory that when it is not set–ActiveSync doesn’t work. As a Domain Admin, it’s automatically turned off. This experience forced me to do the proper “best practice” of removing myself as a domain admin and using another account for super-user operations. I don’t really count this as a problem because it only affected me. I hope that doesn’t disqualify me!
CyberArk: Absolutely not. Congrats again on a smooth and successful migration! Any parting words?
Thomas: I have to hand it to Microsoft, they really did make it easy. We haven’t had any routing issues, in fact mail-flow is much better. Smart phones work just fine, everything is amazing.
If you’d like to reach Thomas to congratulate him—or to learn more about his story—feel free to contact him on your preferred social network: