A great deal has happened in the World of Microsoft since my last post and indeed in the world of Ed. But the soon to arrive Windows Server 2008 R2 End of Support is likely to be bigger than all of those!

Since my last post this time last year, several feature updates of Windows 10, a new Long term servicing release of Windows Server, that being Windows Server 2019 and almost constant updates , releases and developments in my other tech passion Microsoft Enterprise Mobility & Security suite of products have all been released into the wild.

For me as well and becoming a grand parent I have carried on as a freelance consultant, MCT and luckily an MVP as well. This blog has now had a slight refresh and will now focus on Microsoft Azure, Windows Server, EM&S and Certification only.

What next?

So for his post I am going to concentrate on the end of support for Windows Server 2008 R2 on 14th January 2020. Not that far away and there are many hundreds of thousands of servers affected by this deadline. But what does it really mean.

Well Microsoft mainstream operating systems generally receive full updates 5 years from the date of general availability, this means security, feature and other critical updates will be received. Then for the next five years only security and critical updates will be received, no new features. At the end of 10 years you have three options for your servers running the out of support OS, if you want to remain safe secure and compliant.

1. Replace / migrate / upgrade to an OS that is supported (this is not the time to discuss in-place upgrades of server operating systems, maybe another post on that)
2. Pay for up to 3 years of extended support for security updates (this could cost as much as 75% of the original license cost for each server for each year)
3. Host your Server 2008 R2 workload in Microsoft Azure where you will receive those extended support updates free for up to 3 years. (to host this in Azure you would either need Azure Hybrid benefit which is part of the software assurance product set, or to pay for you license as part of the IaaS offering within Azure)

There are, as of today, 152 days left until this happens (today is Thursday 15th August 2019), for some that is a daunting task, so lucky for you Microsoft has provided the Windows Server Upgrade Center to help you out.

How do we do it?

This site will guide you through all the steps at every stage of upgrade from anything from Windows Server 2008 R2 to Windows Server 2019. All the steps, pre-requisites and alternatives are clearly laid out for you with screenshots and required commands too.

Are there limits?

As you can see below its not always a single step process, so Windows Server 2008 R2 has to be upgraded to Windows Server 2012 before you can then upgrade to Windows Server 2019, the general rule is that an upgrade is possible two steps forward only. See the chart below.

There is also plenty of advice on the Microsoft docs site about when you may want to upgrade or migrate

Next week: Look out for the post on Windows Virtual Desktop in Microsoft Azure