Finding statistics on the market share of individual server operating systems in use is difficult as nearly all don’t access the internet directly via a browser, which is the standard way OS statistics are gathered. Website SmartProfile shows a grand total of 35% of servers are running 2008 R2 as of May 2017. Spiceworks 45.4% of servers were running 2008 R2 as of June 2016. Although these statistics are out of date, they do show the huge numbers of 2008 R2 servers that are still around.
The increase of cloud services such as Azure and AWS have made a significant dent in how many 2008 R2 servers there are, as people take the opportunity to migrate to a later version of an operating system when migrating to the cloud. However, it is still safe to presume that 2008 R2 is still alive and kicking in a lot of companies.
Why you should upgrade your Windows Server
Security is always first and foremost. These servers often run business critical functions from certificate authorities to websites to Exchange servers. So not receiving patches leaves them exposed more and more, each passing day after the end of life date.
it also means you can’t get the Cyber Essentials certificate to reassure your customers, since a basic requirement is running supported software providing necessary patches (see here for the full requirements).
You also miss out on the many improvements that have been made with Windows Server 2012 R2, 2016 and 2019. Improvements such as storage spaces, Azure file synchronisation, data deduplication, containers and Hyper-V improvements. A full comparison from Microsoft is here if you would like a comprehensive list.
Unlike a Windows Desktop OS, migrating a server is always a trickier task. There is of course the in-place upgrade option for Windows Server. But what if the server is business critical and downtime is unacceptable? What if the in-place upgrade requires the removal of features (such as Hyper-V) before it can be upgraded?
In a virtualised environment the easiest way would be to create a replacement server and use clustering or failover services to duplicate settings from the old server to the new one.
A more extreme solution is to remove the need for a server entirely by migrating the services it provides to the cloud. SQL databases, websites, Active Directory, file storage and more can all be migrated to run directly in Azure with no dedicated virtual machine required.
Of course there is a temptation to only migrate to the ‘next’ operating system, Windows Server 2012. However, support for that ends in 2023. In our view it’s best to select Windows Server 2016 (end of life 2027) or Windows Server 2019 (end of life 2029). Or even go straight to Azure.
More information and help
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