Should you migrate Windows Server 2003 workloads to the public cloud?

Some who are planning their migration away from on premises Windows Server 2003 have wondered if instead of migrating to an on-premises hosted version of Windows Server 2012 R2, they should instead migrate their workloads to the public cloud.

The answer to this, and all complex questions, is “it depends”.

If your organization has no experience running workloads in the public cloud, you shouldn’t plan on migrating your existing workloads there as part of your migration away from Server 2003. This is simply because the migration away from Server 2003 is going to be complex enough, no reason to add to the complexity by also migrating into the public cloud.

If your organization has substantive experience running workloads in the public cloud, then migrating on-premises workloads from Server 2003 to the cloud is a safer bet. This is because you’re likely to be far more aware of the intricacies of migrating workloads to the cloud and you’re unlikely to get tripped up in the way that an organization that’s new to running workloads in the cloud may.

Another key aspect to consider is that not all workloads run well in the cloud. On top of having to assess which workloads to migrate from Server 2003 and how to migrate them, you’ll also have to figure out if they run in the cloud.

At this stage in the game your aim should be to get workloads off Server 2003 in the most efficient manner possible. Once you have accomplished that goal, you can start worrying about migrating those workloads to the cloud.