Assessing Your Windows Server 2003 deployment

One of the first things you need to do when planning a migration from Windows Server 2003 to another platform is determining the order in which to migrate workloads. This comes down to how you answer the following question:

Lets put aside the question of “how do I know a workload is easy or hard to migrate” and instead assume that any standard workload except IIS that comes “out of the box” with Windows Server 2003 will be an easy workload. This isn’t always the case (DHCP and Remote Access are harder to migrate than file servers) but functions as a good general rule.

My advice on this is to deal with the low hanging fruit first. Dealing with the easy stuff gives you the following benefits:

In terms of assessing your Windows Server 2003 deployment. Sort the workloads into “easy and hard” lists. It doesn’t matter if your list is entirely accurate, but start with the easy to migrate workloads first. Once you’ve worked through that list, move on to the hard ones. Even if you don’t hit the EOL deadline, you’ll have migrated more of your computers across if you get the easy ones out of the way first rather than if you deal with the more time consuming ones first.

There are circumstances where you’ll ignore this advice (for example security concerns) – but it’s a good general guideline.