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We are approching an important milestore: January 14, 2020 sets the end of Extended Support for Windows Server 2008 and 2008 R2. Just three years ago was the turn of Windows Server 2003 (End of the extended support for Windows Server 2003 family).

End of support means the end of regular security updates, potentially leaving you vulnerable to security and compliance issues. Find all the details you need in the end-of-support blog post.

Considering that Windows Server 2008 R2 has a still huge adoption it’s type to considering moving to Windows Server 2012 R2 or 2016. For sure, wait for Windows Server 2019 will mean going out of time for the migration, and also have a technology gap too big.

Planning and executing an upgrade can take some time, so could be important start now and consider the different options.

And there are also new options to help keep your workloads safe after the deadline in order to you protect server workloads if you are not able to upgrade to the latest operating system before the deadline:

  1. Migrate your Windows Server 2008 and 2008 R2 workloads to Azure Virtual Machines and receive free Extended Security Updates until January 2023.
    Find out more about Windows Server on Azure and how you can migrate your skills as easily as your workloads in the ebook The Ultimate Guide to Windows Server on Azure.
  2. Purchase Extended Security Updates for on-premises servers running Windows Server 2008 or 2008 R2 and continue protection for up to three years.
    It’s a great option to keep server workloads protected while you upgrade.
Andrea MauroAbout Andrea Mauro (2857 Posts)

Virtualization, Cloud and Storage Architect. Tech Field delegate. VMUG IT Co-Founder and board member. VMware VMTN Moderator and vExpert 2010-18. Dell TechCenter Rockstar 2014-15. Microsoft MVP 2014-16. Veeam Vanguard 2015-18. Nutanix NTC 2014-18. PernixPro 2014-16. Several certifications including: VCDX-DCV, VCP-DCV/DT/Cloud, VCAP-DCA/DCD/CIA/CID/DTA/DTD, MCSA, MCSE, MCITP, CCA, NPP.


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