In "DNS-AD Rescue," InstantDoc ID 94736, you'll find a cautionary tale about how things can go sideways when you don’t have a plan for your technology upgrade. Here, I’d like to share with you how I believe you should prepare for a major upgrade.

Step 1: Understand What You're Upgrading To
The first step is to educate yourself about the new technology. Suppose your boss instructed you to upgrade your company's aging Exchange Server 5.5 mail server to Exchange Server 2003. Simply inserting the 2003 CD-ROM into the production Exchange 5.5 server during working hours would not only be a bad idea, it wouldn't work. By educating yourself, you'd learn that there's no "in-place" upgrade path for Exchange 2003 as there was for Exchange 2000 Server. You'd also learn about the need for each resource mailbox (Calendars, usually) to have its own network account. And you'd learn another crucial fact: You need Active Directory (AD) before you can install Exchange 2003. To those of you who work with Exchange every day, these facts seem obvious. However, to someone who has worked only with Exchange 5.5, this is all new knowledge that you must know before upgrading a production server.

How do you educate yourself? You have many options. If you can afford it (or your company will pay for it), I recommend a formal, week-long class. This type of training puts you directly in front of the new technology for some hands-on experience and gets you away from everyday on-the-job distractions. If formal training isn’t an option, a few good books that have practice labs for you to work through should point you in the right direction. And don’t forget online forums, Microsoft Webcasts, and the free white papers and technical documents that Microsoft publishes.

Step 2: Document Your Current and Planned Setup
After you have a better understanding of the technology that you're about to implement, it’s time to document. If you don’t already, you should have a complete drawing of the current network that you want to upgrade. To expand on the Exchange-upgrade scenario, your IT organization should have a drawing of every Exchange server with its service pack level, the Exchange 5.5 sites they're in, their physical location, where mailboxes are located, what ports they use through the firewall, and other pertinent information. You might have modified the registry to force Exchange to use only certain ports, or perhaps you have third-party software (e.g., antivirus, antispam) installed. Document those facts as well.

Use the drawing of your current setup to start planning the upgrade. Don’t worry about getting it 100 percent correct the first time. The idea here is to take what you know about your current network, as well as what you might have learned in class, and start to formulate a plan.

Here are examples of items you might write down:

  • Plan AD upgrade! Explain to management the requirements for Exchange 2003.
  • Back up current Exchange 5.5 server and test the restore on a test network.
  • Exchange 5.5, Enterprise Edition server behind the firewall will be upgraded to Exchange 2003 Enterprise.
  • Server in the demilitarized zone (DMZ) that proxies Microsoft Outlook Web Access (OWA) will be removed, and a fresh new Exchange 2003 front end will be installed.
  • Backup and antivirus software will have to be upgraded to be compatible with Exchange 2003.
  • Need procedures for moving Secure Sockets Layer (SSL) certificate from old 5.5 OWA to new 2003 OWA.
  • Will need to alter firewall settings to OWA (port 443) and SMTP (port 25) traffic to flow to the new server.
  • Purchase a new server as the current 5.5 server does not meet the minimum requirements for 2003.
  • "Phase Two": Turn on RPC over HTTP so remote salespeople can use Outlook securely over the Internet without a VPN.

By now, your plan should be starting to come together. You have some idea of what you want to accomplish and how to do it, but there are probably some lingering questions. You have a preliminary plan; now it’s time to test it.

Step 3: Test the Plan
Testing can be as simple as gathering some old workstations or using a virtualization product such VMware Server or Microsoft Virtual Server and performing a mock upgrade. Start with machines that aren't connected to your production network, install Exchange 5.5 (or whatever version you're upgrading from) so that it mirrors your production environment, add in some users, and start the upgrade process. Many times, your first stab at the upgrade won't go smoothly. Something will go wrong. This is the time to learn from your mistakes, update your documentation, and start again. Run through the plan as many times as it takes until you're comfortable with the upgrade and the new technology.

Step 4: Perform the Upgrade
Now you should have a complete plan that you're comfortable with. You've learned the new software, tested and documented a plan, and are ready to perform the upgrade. This is the most important step and is what you've been working toward. If downtime is required, be sure to coordinate the upgrade schedule with the rest of the company. This step seems obvious, but I once worked for an administrator who thought nothing of applying a service pack to an Exchange Server 5.0 server during lunch! "They can live a few minutes without email," he said, in total seriousness. How many times have you been interrupted at the bank or doctor’s office because their IT department didn’t take their customers into consideration? This isn't the type of attitude that you want to have. You want to be known as an administrator who goes the extra mile to keep downtime to a minimum.

On the day of the upgrade, be sure to follow your plan! Don’t take shortcuts. If your roadmap to success calls for a backup halfway through the process, take the time to perform the backup. Maybe you decided to perform half of the upgrade on Friday evening and the rest Saturday after you’ve had some rest. Follow your plan! Don’t pull an all-nighter if you didn’t plan for it. Only upgrade the components that you documented—resist "scope creep." Follow your plan!

Step 5: Take Stock
After you've successfully performed the upgrade or installed the new technology, it’s time to sit back and admire your work. Give yourself a pat on the back. You developed your plan and implemented the new technology according to your plan. But don’t sit too long. The last step is to think about the things that didn’t go right. What did you miss? Was your original network drawing correct? If not, take the time now to update them so that it makes your job easier for the next upgrade. Perhaps it took you longer to complete the upgrade than you'd scheduled downtime for. If something happened that wasn’t in your plan, write it down so that you won’t make the same mistake next time.

Remember: Have a plan before starting. Once you've documented the plan, test it first, then implement it. Plan your dive; dive your plan. This is the key to success.