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Karl-WE's avatar
Jan 30, 2024

BLOG: Windows Server Installation guidance / M365 Support on Windows Server


Windows Server 2025 will probably be released later this year. At least signs / stars seem to align. ๐Ÿ™‚ 

Starting with this Windows Server release, Microsoft 365 Apps for Enterprise are supported within the mainstream support of the OS. That means 5 years peace of mind, after the release of the next Windows Server OS.

For more information review the official matrix. Windows Server 2025, should be included after release. The latest Office Support Matrix can be obtained here

Windows Server 2025 will be released this year with load of significant improvements over 2022 or earlier versions. Please check this announcement + comments, and find more here in the Windows Server 2025 AMA.
Feel invited to join the Windows Server Summit and if you cannot attend, learn what's new watching the recorded sessions.


This announcement and rich improvments, will make any migration plans worthwhile, noted Windows Server 2016 is already in Extended Support. Will outline later why this isn't a good thing for most. Windows Server 2019 just entered Extended Support this month.
 

Obtaining and maintain Software Assurance for Windows Server through Volume Licensing or CSP Subscription (SA equivalency) makes sense for you this year in several ways

  • for the adoption of the new Windows Server 2025 release

  • Significant cost reduction through Azure Hybrid Benefits, among others for all licensed cores under SA or SA equivalency. This is not a licensing advice post, rather presents you common examples.
    For details hold on to Product Terms, as conditions may change.

    • free Windows Server Datacenter OS licenses (even if on-prem only Standard licensed) in Azure. For Details hold on to Product Terms, conditions may change.

    • free Azure Stack HCI usage for licensed cores

    • free of charge access to the Windows Server Datacenter Azure Edition VM or ISO within Azure and when running on Azure Stack HCI, granting you exclusive features, but will also appear with Windows Server 2025.

    • per VM licensing on-premises on Azure Stack HCI and in Azure (currently with a minimum 8 cores per VM (vOSE))

    • dynamic licensing with Windows Server 2025*

      *SA or equivalent not required


Use Microsoft (server) products, within mainstream support wherever possible
especially, when production critical.

Some (german) software manufacturers also specify that the Windows Server OS must be in mainstream support in order for their software to be supported. Microsoft 365 joins this chorus now.
Caveat: Microsoft Exchange Server on-premises is currently only available in Extended Support (MS Exchange Server 2016 / 2019). So only the OS (WS 2022) can be kept in Mainstream support at the moment.

Reasons against operating products in Microsoft Extended Support:

  • support comes at extra costs
  • hard to obtain / not immediately available, especially in emergencies
  • there is no guarantee of solution or workaround
  • Microsoft sometimes removes or replaces documentation of products outside of mainstream support
  • Extended Security Updates are costly (free on Azure Stack HCI on-prem / and when running in Azure)

Install Windows Server always in english language (en-us), if necessary use Language Packs (LP) / LIPs

Reasons and pain points from the field:

  • Microsoftโ€™s / own PowerShell scripts or modules may be language dependent, e.g. Windows Features, local security groups etc.
  • mass evaluation in Server Manager or PowerShell are hindered, as Eventlogs, Roles & Features and Windows services descriptions are language dependent. For example this renders full text search in Server Manager unhelpful.
  • some roles are language dependent and therefore cannot be (easily) migrated (e.g. DHCP, AD CS)
  • Documentation and error messages are easier to find and understand in English (crude translation) + operational bonus for Microsoft CoPilot in Edge, possibly replacing Dr. Google (Mechanical Doctor) when searching for solutions ๐Ÿ™‚ 
  • way easier collaboration with Microsoft Support
  • proven fewer problems with Windows Admin Center
  • GPO Search Engine only exists in English. The translation of GPOs is very arbitrary.
  • Direct in-place upgrade to Windows Server Azure Edition possible, when switching to Azure Stack HCI
  • Windows Server 2022 and 2025 Support dynamic user based language packs (LIPs). Internet connection is required for download and updates.
  • Bonus: You can leverage group policy to assign OS language, keyboard and regional settings based on user, or AD group membership. 

 

Choose / prefer to install Windows Server as Core option where possible
This will enhance your "need" to adopt RBAC and Remote Management without RDP.

  • Possible usecases: Domain Controller, Exchange, SQL (GUI Setup exists), FileServer etc.
  • Remote Management via Privileged Admin Workstation (PAWS :paw_prints:) / Windows Server VM (RDSH) + Tools
    • Windows Admin Center
    • Server Manager
    • DSAC and other RSAT tools
    • sconfig

Install Windows Server only as UEFI / GPT

 

  • Windows Server 2022 and 2025 support VBS and Secured Core settings.
    GPT / UEFI is a prerequisite for this.
  • Windows Server 2022 / 2025 can use vTPM for Bitlocker and other things like Windows 11.
    GPT / UEFI is a prerequisite for this.
  • easier migration paths VMware <> Hyper-V / Azure Stack HCI. These VMs are deployed as Gen 2 Hyper-V. Gen 1 VMs or VMware BIOS VMs are no longer preferred, see above.

Keep the WinRE partition behind the OS partition

  • easier maintenance of the OS in an emergency
  • Uninstall of defective Windows Updates before the boot process (starting with Windows 2022)
  • Re-Partitioning / Resizing using 3rd party tools possible via VHD(X) / VMDK mounting in another VM if required.
  • You can find more information on WinRE and WinRE patching considerations in this guidance


As you've made it to the end of this lengthy and hopefully helpful post, here's your bonus material / extended edition: Windows Server Upgrade guidance.


Thanks for reading and adopting changes to your environment and strategy!

  • On first of November 2024, Windows Server 2025 has been released.

     

    Please take your time reading about Windows Server Installation guidance and other guides included into this article.

     

    To celebrate this release and updating the original article, make yourself familiar with the official release notes and known issues and limitations

     

     

    Happy deployment and upgrading!

     

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