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Planning the timeframe for the upgrade.Make sure your server is up-to-date and fully patched before doing an in-place upgrade.
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You can directly do an in-place upgrade to Windows Server 2019 from Windows Server 2016 and Windows Server 2012 R2. To help you with Windows Server upgrades, the Windows Server team created Windows Server Upgrade Center, which gives you step-by-step guidance for modernizing your datacenter. You can find more information about Windows Server 2019 installations and upgrades on Microsoft Docs. This blog post covers how you in-place upgrade Windows Server 2008 R2 to Windows Server 2019.
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There are many ways you can migrate your server applications to a newer version of Windows Server.
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If you want to have more information about how to migrate your servers to Azure, check out the Azure migration center. Customer will need to upgrade their Windows Server 2008 and Windows Server 2008 R2 to a newer version of Windows Server or migrate these servers to Microsoft Azure and get three years of extended security support for free, which will give you more time to upgrade your servers, redeploy your apps or rearchitect your applications. As you know the Windows Server 2008 and Windows Server 2008 R2 are out of support on January 14th, 2020.