The World According to Mitch

The first public presentation that I delivered to a Microsoft community audience was the launch of Windows Server 2003 R2. As a user group leader at the time, I was sent a copy of the product, along with a lot of materials to help me to deliver the presentation in the MPR room at Microsoft’s Montreal offices. It was a learning experience to be sure, but it was also the first time I had to learn a system to present it before I had used it. I still remember some of the great features I talked about that night… years before features like Hyper-V and Server Core would be introduced to the world. That was over sixteen years ago… in December 2005.

As a Virtual Technical Evangelist with Microsoft Canada, I had the honour of being part of the launch event in Toronto, and then the launch tour across the country. At the same time, it feels like yesterday that Damir and I took the stage… and a thousand lifetimes ago. That was the only Server operating system that I would launch as an evangelist; by the time Server 2012R2 would launch (in October 2013) I had already left for Rakuten. It was on behalf of Rakuten that I was able to attend an early airlift of Server 2016… and that (the last time I was on the Microsoft campus in Redmond) feels like a very long time ago indeed.

When I received a notice that mainstream support for Windows Server 2016 ends on January 11, 2022 (in less than a month), I was a bit jarred. I always try to build servers with the latest and greatest operating system that is supported by my client, which for one particular client I am working with is Server 2019; it was just last month that I discovered that for a particular workload I would need to install a new Server 2016 instance, and I did. After all, it is still modern, right? That was my thinking at the time. It is surprising to realize that the OS celebrated its 5th birthday in October! While that is not old, it makes the OS two full generations out of date, with the launch of Server 2022 this past August.

What does it mean? Let me explain what Mainstream Support is, and what happens now.

In Mainstream Support, you can request changes to the product design and features. Microsoft releases both Security and Non-security updates.

When Mainstream Support ends, the operating system falls into the Extended Support period. For Server 2016, this will extend for five years beyond the end of Mainstream Support… to January 12, 2027. What this means is that you cannot make any change requests to the product, but Security updates will still be released on a monthly basis. For organizations who pay for Unified Support, Non-security updates will be available from time to time as well.

The End of Support, sometimes called the End of Life of Server 2016 will be January 2027. After that, Security updates will only be made available through the Extended Security Update Program, In short, if you are a company with very deep pockets that wants to pay through the nose to extend the lifespan of an operating system, then ESUs will deliver Critical and/or Important security updates for a maximum of three years after the product’s End of Extended Support date.

It is easy to say ‘Why spend the money? Take the time to upgrade your server operating systems, and you will never have to deal with operating systems that are end of life.’ I can tell you from personal experience, it is not always that easy.

In 2019 I was responsible for the Windows Servers at a major entertainment studio in California. One of my first responsibilities was to track the migration of servers off Server 2008 R2 (end of life was January 2020). When I started the role there were more than 600 servers on the legacy OS. The problem was that none of them ‘belonged’ to my team; they were assigned to other teams, and my team had to support them. I had to reach out to the owners of those servers and work with them to migrate software (a lot of which was not compatible with Server 2012, let alone 2016) and data off those servers. Getting people in Hollywood (we were not in Hollywood, but everyone in the movie business in California is ‘in Hollywood’) to understand that they needed to do things that they would not see tangible benefits from… let’s just say that it would have been easier than herding cats.

By the end of my tenure (in October 2019) we still had over 450 servers on Server 2008R2, and the director of IT had made the decision to start paying for extended security updates. Having unsupported servers was not an option… this might have been the same movie studio that just four years before I joined the team had been the target of a massive (and very public) hack. Security was so tight that it made working more difficult. End-of-life servers are a security threat.

While I understand how it can happen that systems get that old, I do not accept it as a necessity. A company that is on the ball will start testing their applications on newer operating systems almost as soon as those operating systems are released. Had this company done that, they would have started in 2012, and I would never have been aware of the issue. Waiting until 2019 was short sighted at best.

If you have dozens or hundreds of servers running Server 2016, don’t worry… they will still be secure and supported in February. However, you should know that it is time to start upgrading them. Yes, there are workloads that will not work on any later operating system. Exchange Server 2016, for reasons that I cannot fully explain, is not supported on Windows Server 2019. Does that mean you should leave those workloads on Server 2016? No. It means that over the next few months you should be exploring upgrading those workloads to a later version that will be supported on a later operating system.

In 2003 and 2004 there was a campaign by Microsoft for Windows Small Business Server, showing that it was so easy to install and maintain that you did not need an IT professional to do it. I seem to recall one case study in which a dentist installed and supported his own server environment. With new servers that may be fine, but when end-of-life comes a-callin’, you need professionals for this, lest you find yourself with an unsupported and unsupportable server environment.