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Microsoft explains the updates from Windows Server 2008 R2 to Windows Server 2019

The end of Windows 7 Service Pack 1 support in January 2020 marks the end of Windows Server 2008 R2 support; as do clients running Windows 7 on workstations. Clients using the Server version must decide what to do about it.

One of the options available to Microsoft customers is to upgrade to a supported Server version. The path may not be the most appropriate for some use cases because it involves multiple upgrades and not just one upgrade from Server 2008 R2 to Server 2019.

Microsoft has published a detailed guide on upgrading to the latest version of Windows Server. The company wants its customers to upgrade to Windows Server 2019, but it is certainly possible to upgrade to an older but still supported version (2012 R2 and 2016).

Upgrading procedure for Windows Server 2008:

  • Upgrade Windows Server 2008 R2 to Windows Server 2012.
  • Upgrade Windows Server 2012 to Windows Server 2016.
  • Upgrade Windows Server 2016 to Windows Server 2019.

Support for Windows Server 2012 and 2012 R2 ends in 2023 and customers can stop the upgrade process immediately and theoretically.

There are a few caveats that administrators should be aware of. Microsoft notes that some server roles or applications may not be migrated to more recent versions of Windows Server.

Microsoft recommends that administrators create full backups of server systems before the upgrade is completed.

Administrators must include the following in a checklist to plan and prepare for the upgrade to a new version of the server:

  • Which software and roles are installed on the server and are supported and work with the new versions of Windows Server. I recommend to make an inventory of the software and check if applications and roles are supported.
  • Prepare some tests to see if the app is still working after the upgrade. It’s a good thing to do these tests before the upgrade as well, so you can confirm that everything is working properly.
  • If it’s a physical server, do you have drivers and firmware updates for the new version of Windows Server available?
  • Think of backup software and antivirus, you may need to uninstall them during the update process and reinstall them once the upgrade is complete.
  • Make sure your server is up to date and fully patched before you upgrade on-site.
  • Planning the duration of the upgrade. On-site upgrades take some time, so make sure you have a long enough maintenance window planned. Also be sure to provide the maintenance window, so users know that the app or service won’t be available.
  • Make sure you have a backup of the server before you start the upgrade process, and make sure you can restore from that specific backup.
  • If possible, test the upgrade process with a non-production server.
  • Make sure you have enough disk space for the upgrade.
  • Gather your system’s information before the upgrade.

The server will be unavailable for a period of time, since three upgrades will be executed one after the other, even if all upgrades run without any problems.

The main advantage of upgrades is that most configurations and applications are retained. A new installation of Server 2019 may be faster, but it would require a lot of work to install the necessary applications and change the configuration.

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