Why Windows Server 2008/2008R2 EOL is closer than you think

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“I love deadlines. I love the whooshing noise they make as they go by”  - Douglas Adams. Author, Hitchhikers Guide to the Galaxy


It’s not just people that are excellent procrastinators. Organizations are excellent procrastinators as well. When a deadline exists with another year in its date, it’s easy to convince yourself that dealing with it is not particularly urgent. Even though Microsoft was shouting from the rooftop for years about the end of support for Windows Server 2003, many organizations didn’t really start doing anything about moving their fleet of computer off the operating system until the deadline was right on top of them. When it came to getting people to migrate off Windows Server 2003, attrition by hardware failure seemed to be more effective in getting recalcitrant organizations off Windows Server 2003 than planned migration did.


And even though Microsoft has made it abundantly clear that the end of support for Windows Server 2008 and 2008 R2 is rapidly approaching, there appears to be a similar lack of urgency felt by many organizations about transitioning away from the operating system.


The Windows Server 2008 / 2008 R2 EOL deadline is closer than you think. It’s closer than you think for the following reasons:


  • Although you can make a ballpark estimate on how long it will take to migrate all your workloads away from Windows Server 2008 or 2008 R2, you don’t really know how long it will take to migrate a specific workload until you’ve actually migrated it.
  • Any ballpark estimate that you make, unless you’ve performed a large number of migrations, is going to be a guess. This is because unexpected things happen and that it’s hard to come up with a reliable estimate about the amount of time needed to deal with unforeseen issues.
  • Although it’s possible that you might migrate workloads more quickly than you estimated you would, the reality is that it’s more likely that your estimates are wildly optimistic

Windows Server 2008/2008 R2 EOL is 14th of January 2020. While you can get an extension if you migrate to Azure of having that date pushed out by 2 years, just remember that migrating to Azure may involve as much planning, resources, and effort as migrating to Windows Server 2016 or Windows Server 2019 would.

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