With the accelerating pace of development and more frequent releases, we are seeing a bunching up of SQL Server support milestones. From 2008 through 2016, we had a new version every two years. Last year we saw another version, which means 5 versions in a ten year span. With 5 years of main support and 5 of security patches + extended support, Microsoft has quite a few active branches of code.

We now see SQL Server 2008 and R2 coming to the end of support on July 8, 2019. There are plenty of options for customers, including doing nothing. After all, if you've been running SQL Server 2005 or even 2000, you've been without support for some time. That might not be a policy of your organization, particularly if you adhere to any standards or are bound by regulation. In those cases, you may need to have active support under contract.

There is a good argument to be made that you should have active support for your core systems, such as the OS or your database platform. If a bug or security issue is discovered, would you want to upgrade on a very short timeline or apply a patch to your existing version? Think about running SQL Server 2008 today and a critical security problem is discovered in October. Do you want to upgrade to SQL Server 201x this year? Or would you wish that you would have planned and executed an upgrade in June and have to apply a GDR patch in October?

I tend to view patches as much lower risk than an upgrade, mostly because the number of changes is smaller, and an upgrade reduces my options, not to mention often increases my costs. That might change over time, as I upgrade other instances and gain experience with a new version. SQL Server 2017 still feels new to me, but SQL Server 2014 and SQL Server 2016 feel older. If I had to perform an emergency upgrade to an instance, I'd be more comfortable moving from 2008 to 2016 than 2017 right now.

I wonder how many of you view the upgrades as more risky? These days the migration tools analyze for keyword issues, and many of those can be alleviated with compatibility levels. Perhaps some of you aren't worried and will run your SQL Server 2008 instances until they die, only upgrading if forced. If so, let us know. 

If you've got R2 instances, however, please get rid of them. The sooner we get rid of this horribly confusing version name, the better.

One late note, after this was written, Microsoft offer to add additional extended support if you migrate to Azure.