Calling all Windows Server 2008 R2 users. The End is Nigh

Microsoft has a very well defined policy for supporting its products, of all types There is mainstream support, extended support and then no support at all. (There is an extra level where you sign a contract to receive special support after the end of extended support period has been reached. This contract is not for normal people of organizations and I dread to think of the cost of one) This blog post is designed to walk you through the venerable Windows Server 2008 (and R2) timeline and hopefully help you make the move to a more modern, secure and feature-rich server operating system.

So, what are the important dates for Windows Server 2008 R2, what do they mean? and how do I avoid a last minute rush?

Lots of questions there, first the Mainstream support for Windows Server 2008 R2 ended quite sometime ago, checkout the impact of this on your server estate.

Essentially for five years from release Microsoft will provide new features as well as security and non-security updates. For the next five years, no new features will be added but you will continue to receive updates. These updates fix security holes, and new attack vectors. Non security updates are also provided.

What sort of updates, what sort of attacks are prevented? The graphic below shows some well know critical and non-critical security updates over recent times.

Without these your infrastructure is at risk of exploits and all your good work securing your networks and applications would be undone.

Now the bad news, the 5 year Extended support period for Windows Server 2008 R2 ends on January 14th 2020.

The SQL Server date is even closer at July 9th 2019

If you are still using these platforms in production after those dates, they are unsupported.

Microsoft has a number of options and resources to assist you to migrate onto a more modern Windows Server operating system. Bear in mind that Windows Server 2012 is no longer available for sale and if you want to use that you would need to take advantage of the downgrade rights available with some licensing options.

In the autumn (fall) Windows Server 2019 is to released, so you have a couple of decisions. Do you wait until it is available or purchase now. If you purchase now, you can use software assurance (as an add on to your purchase) to allow you to upgrade to Windows Server 2019 with no addition licensing costs.

Which should you choose?

This handy chart shows you which features each of the more modern versions contain.

There is an additional decision to be made as well. Do you replace your older out of support (soon) servers by migrating to Azure or for new on-premises servers and go for OEM or ROK licences, which are often the cheapest licenses for new servers.

The final consideration would be for server CALs (Client Access Licences). If this is your first Windows Server at a new version such as 2016 or 2019 then you would need to upgrade (replace) your Server CALS as well (either device or user CALS). Despite being an honesty based licensing system, you do not have rights to connect non administrative users to the server remotely without a CAL covering every user or device.

Where to start though. well you need to assess what in your current environment requires replacing, the hardware, software and licenses. Microsoft have a handy chart for this too.

You may well find that this is a perfect time to consider a hybrid solution for the first time. Future blog posts will cover the hybrid advantages of Windows Server 2016 and Windows Server 2019.

Don't delay get migrating today.

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