Microsoft explains in-place upgrades from Windows Server 2008 R2 to Windows Server 2019

Martin Brinkmann
Jul 23, 2019

The end of support for Windows 7 Service Pack 1 in January 2020 marks the end of support for Windows Server 2008 R2 as well; like customers who run Windows 7 on devices, customers who run the Server pendant need to decide what to do about it.

One option that Microsoft customers have is to use the in-place upgrade to upgrade to a version of Server that is supported. The path may not be the most appropriate for some uses cases as it involves several upgrades and not just a single Server 2008 R2 to Server 2019 upgrade.

Microsoft published a detailed guide on using the in-place upgrade route to upgrade devices running Windows Server 2008 R2. The company wants customers to upgrade to Windows Server 2019 but it is certainly possible to upgrade to an older but still supported version of Server instead.

Windows Server Upgrade Path

Administrators who want to take the in-place upgrade route need to run three upgrades in total:

  • 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.

Windows Server 2012 and 2012 R2 support ends in 2023 and customers may stop the upgrade process right then and there theoretically.

There are a couple of caveats that administrators need to be aware of. Microsoft notes that some server roles or applications may not be migrated to newer versions of Windows Server.

Microsoft recommends that administrators create full backups of the Server systems before the upgrade is run.

Administrators should include the following items on a checklist to plan and prepare the upgrade to a new Server version:

  • What software and roles are installed on the server and are they supported and working with newer versions of Windows Server. I recommend doing a software inventory and check if the applications and roles are supported.
  • Have some tests ready to check if the application still works after the upgrade. It is a good thing to run through these tests before the upgrade as well, so you can confirm everything is working correctly.
  • If it is a physical server, do you have drivers and firmware updates for the new Windows Server version available?
  • Think about backup software and antivirus, you might need to uninstall these during the update process and reinstall it after the upgrade is done.
  • Make sure your server is up-to-date and fully patched before doing an in-place upgrade.
  • Planning the timeframe for the upgrade. In-place upgrades take some time, make sure you have a long enough maintenance window planned. Also make sure you communicate the maintenance window, so users know that the application or service is not available.
  • Make sure you have a backup of the server before you start the upgrade process, and make sure you can also 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 information before the upgrade.

The server will be down for quite a while considering that three in-place upgrades are run one after the other even if all upgrades run without any issues.

The main advantage of in-place upgrades is that most configurations and applications remain. A new installation of Server 2019 may be faster but it would require extensive work to install needed applications and make configuration changes.

Now You: Would you use in-place upgrade options or install a new operating system version instead? (via Deskmodder)

Microsoft explains in-place upgrades from Windows Server 2008 R2 to Windows Server 2019
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Microsoft explains in-place upgrades from Windows Server 2008 R2 to Windows Server 2019
Microsoft published a detailed guide on using the in-place upgrade route to upgrade devices running Windows Server 2008 R2
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  1. Dan Donx said on January 15, 2023 at 10:29 am

    What mental age of reader are you targeting with the first sentence? 10?

    Why not write an article on how to *avoid* upgrading from W10 to W11. Analogous to those like me who avoided upgrading from 7 to 10 for as long as possible.

    If your paymaster Microsoft permits it, of course.

  2. Dexter said on January 15, 2023 at 11:14 am

    5. Rufus
    6. Ventoy

    PS. I hate reading these “SEO optimized” articles.

    1. cdr said on January 15, 2023 at 3:32 pm

      I used Rufus to create an installer for a 6th gen intel i5 that had MBR. It upgraded using Setup. No issues except for Win 11 always prompting me to replace my local account. Still using Win 10 Pro on all my other PCs to avoid the bullying.

  3. sv said on January 15, 2023 at 6:40 pm

    bit pointless to upgrade for the sake of upgrading as you never know when you’ll get locked out because ms might suddenly not provide updates to unsupported systems.

    ps…. time travelling?
    written. Jan 15, 2023
    Updated • Jan 13, 2023

    1. Martin Brinkmann said on January 16, 2023 at 5:49 am

      This happens when you schedule a post in WordPress and update it before setting the publication date.

  4. Anonymous said on January 16, 2023 at 8:24 am

    Anyone willing to downgrade to this awful OS must like inflicting themselves with harm.

  5. basingstoke said on January 16, 2023 at 11:18 am

    I have become convinced now that anybody who has no qualms with using Windows 11/10 must fit into one of the following brackets:

    1) Too young to remember a time before W10 and W11 (doesn’t know better)

    2) Wants to play the latest games on their PC above anything else (or deeply needs some software which already dropped W7 support)

    3) Doesn’t know too much about how computers work, worried that they’d be absolutely lost and in trouble without the “”latest security””

    4) Microsoft apologist that tries to justify that the latest “features” and “changes” are actually a good thing, that improve Windows

    5) Uses their computer to do a bare minimum of like 3 different things, browse web, check emails, etc, so really doesn’t fuss

    Obviously that doesn’t cover everyone, there’s also the category that:

    6) Actually liked W7 more than 10, and held out as long as possible before switching, begrudgingly uses 10 now

    Have I missed any group off this list?

    1. Heinz Strunk said on September 19, 2023 at 3:57 pm

      You have missed in this group just about any professional user that uses business software like CAD programs or ERP Programs which are 99% of all professional users from this list.

      Linux doesn’t help anyone who is not a linux kid and apple is just a fancy facebook machine.

  6. ilev said on August 24, 2023 at 7:34 pm

    Microsoft has removed KB5029351 update

    1. EP said on August 24, 2023 at 9:21 pm

      only from windows update though
      KB5029351 is still available from the ms update catalog site

  7. Anonymous said on August 24, 2023 at 11:05 pm

    1. This update is labaled as PREVIEW if it causes issues to unintelligent people, then they shouldn’t have allowed Preview updates ot install.

    2. I have installed it in a 11 years old computer, and no problems at all.

    3. Making a big drama over a bluescreen for an updated labeled as preview is ridiculous.

    This is probably another BS internet drama where people ran programs and scripts that modified the registry until they broke Windows, just for removing stuff that they weren’t even using just for the sake of it.
    Maybe people should stop playing geeks and actually either use Windows 10 or Windows 11, but don’t try to modify things just for the sake of it.

    Sometimes removing or stopping things (like defender is a perfect example) only need intelligence, not scripts or 3rd party programs that might mess with windows.

  8. john said on August 24, 2023 at 11:17 pm

    Windows 11 was a pointless release, it was just created because some of the Windows team wanted to boost sales with some sort of new and improved Windows 10. Instead, Microsoft cannot support one version well let alone two.

    1. John G. said on August 25, 2023 at 12:08 pm

      Windows 11 is the worst ugly shame by Microsoft ever. They should release with every new W11 version a complete free version of Starallback inside just to make this sh** OS functionally again.

  9. EP said on August 25, 2023 at 3:10 pm

    motherboard maker MSI has recently released a statement regarding the “unsupported processor” blue screen error for their boards using Intel 600/700 series chipsets & to avoid the KB5029351 Win11 update:–UNSUPPORTED-PROCESSOR–Error-Message-of-Windows-11-Update-KB5029351-Preview-142215

  10. EP said on August 29, 2023 at 7:32 pm

    check out the following recent articles:

    Neowin – Microsoft puts little blame on its Windows update after UNSUPPORTED PROCESSOR BSOD bug:

    BleepingComputer – Microsoft blames ‘unsupported processor’ blue screens on OEM vendors:

  11. Leonard Britvolli said on August 30, 2023 at 10:33 pm

    While there may be changes or updates to the Windows 10 Store for Business and Education in the future, it is premature to conclude that it will be discontinued based solely on rumors.

  12. sembrador said on September 5, 2023 at 9:32 pm

    My advice, I left win 15 years ago. Now I’m a happy linux user (linuxmint) but there is Centos, Fedora, Ubuntu depending on your needs.

  13. EP said on September 6, 2023 at 11:55 am

    motherboard maker MSI has recently released new BIOS/firmware updates for their Intel 600 & 700 series motherboards to fix the “UNSUPPORTED_PROCESSOR” problem (Sept. 6):–UNSUPPORTED-PROCESSOR–caused-BSOD-on-MSI-s-Intel-700-and-600-Series-Motherboards-142277

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