In the last post I mentioned people perhaps migrating from Server 2003 to Server 2008 R2. One of the comments, perhaps anticipating this post, was that it was a better idea to migrate to Server 2012 R2. I couldn’t agree more.
The main reason you should upgrade to the most recent version of Windows Server is simple. Each version of Windows Server is built on the lessons learned from the previous versions. Windows Server 2008 R2 is a more secure OS than Server 2008, Server 2012 than Server 2008 R2, and Server 2012 R2 is built based on lessons learned about Server 2012.
Naturally if you are thinking this way, you’re probably wondering whether it is worth holding off for Server 2016 rather than upgrading to Server 2012 R2. Today’s short answer is a resounding no. We don’t know at this point in time we don’t know when Server 2016 will be released. Before you migrate you should have a good working knowledge of the OS that you’re migrating to. And it helps when there are tools to assist in the migration. If you plan on moving to Server 2016 from Server 2003, it may be 2017 before you start the migration and there won’t be any free tools available to assist with the migration because as far as Microsoft’s concerned, you should have migrated away from the OS before the end of support deadline.