The / Weblogs are moving to Windows Server 2019

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Windows Server 2019

For the past three years, the / Weblogs have been hosted on an infrastructure running Windows Server 2012 R2. This is about to change.


End of support for Windows Server 2008

On January 14th, 2020, Microsoft is ending the support for Windows Server 2008 and Windows Server 2008 R2. For the / Weblogs this would mean they are hosted on the lowest supported Windows Server version available.

As the CTO, I find this unacceptable.

Windows Server 2012 and Windows Server 2012 R2 remain to be supported by Microsoft until October 10th, 2023, so the direct need to switch Operating Systems isn’t high at the moment. It’s the best moment to switch.


Benefits of Windows Server 2019

Of course, a new Operating System adds benefits. We’ve been testing Windows Server 2019 ever since it became available as a supported Operating System in Azure Infrastructure as a Service (IaaS) and even based a book on it. This is what we identified as the top 3 benefits for the / Weblogs:

  1. ECDH
    Windows Server 2019 supports the latest Elliptic Curve Diffie-Hellman (ECDH) cipher suites. This makes it possible to provide perfect forwarding secrecy (PFS) in the encryption that we offer through SSL and TLS.
  2. HTTP/2
    Windows Server 2016 offered HTTP/2 for the first time. We’ll benefit from HTTP/2 with faster load times, encryption on by default, and mobile friendliness through header compression.
  3. HSTS
    With HTTP Strict Transport Security (HSTS), we can guarantee that no unencrypted content is sent. Also, we intend to redirect every visit to the unsecured versions of the / Weblogs to the secured version.



Every migration method has its pros and cons. As our migration method we chose to perform shadow implementations of our infrastructure on Windows Server 2019. This would make for an easy switch, except for the fact that we also want to move to the newest version of MySQL Server. This requires a direct switch on the back-end and forces us to test things thoroughly in this tier. It also requires a period of little changes (though actions like adding blogposts, etc.), so we are planning on making this switch around Christmas 2019.


We’d like to thank you, our readers, for appreciating our content, for your visits, replies, helpful comments and your likes and retweets on Twitter.

Thank you,

DirTeam CTO

Author: Sander Berkouwer

Sander Berkouwer is the author of the Active Directory Administration Cookbook, speaker and blogger at and He is awarded Microsoft MVP, Veeam Vanguard and VMware vExpert. Since 2009, Microsoft has awarded Sander with the Most Valuable Professional (MVP) award. Since 2016, Veeam has awarded Sander with the Veeam Vanguard award.

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