Which version of Windows Server should your migration from Windows Server 2003 target?

In the previous post we looked at why you should target a version of Windows Server that’s currently available when considering your migration away from Windows Server 2003, rather than hanging on until Windows Server vNext RTMs.

When discussing migration away from Server 2003 with IT Pros, I occasionally get asked “well, what if we migrated to Windows Server 2008 R2 instead of Server 2012 or Server 2012 R2?”.

When I probe them about their reasoning for not moving to Windows Server 2012 R2, they suggest the following reasons:

Every environment is different and everyone is under different constraints. While these are certainly rationalizations for not migrating to Server 2012 or Server 2012 R2, they aren’t good reasons for not migrating to Server 2012 or Server 2012 R2.

Consider the following dates:

If your organization still has servers running Server 2003, it’s fair to suggest that there may not be great internal organizational impetus to upgrade workloads and platforms when newer versions come out. By migrating to Windows Server 2012 or Windows Server 2012 R2, you’re going to get almost 3 more years out of the migration target operating system than you would if you migrated to Windows Server 2008 or Windows Server 2008 R2.

And, if your organization does lack the general willingness to upgrade frequently, which approach is more likely to pay off – upgrading to an OS that has just over 5 years left on the clock, or one that has just over 8 years left on the clock?