Upgrade Windows Server 2016 to Windows Server 2019

Upgrade path:

Windows Server 2016 can be upgraded to Windows 2019 in a single upgrade process.

Support:

In-place Upgrade is supported for Windows Server 2016 on physicaL hardware, and in Virtual Machines. Public and private cloud companies also support In-place Upgrade on Windows Server 2016 Virtual Machines to upgrade to Windows Server 2019 – check with your cloud provider.

Alternative:

Migrate (re-deploy) applications and data on a clean install of Windows Server 2019.

Limitations:

• For the smoothest upgrade experience, if you‘ve deployed software-defined datacenter (SDDC) features like Software-Defined Networking (SDN) or Storage Spaces Direct, you are encouraged to wait for validated hardware from the Windows Server Software-Defined (WSSD) program to become available. The first wave of validated hardware is expected very soon; in mid-January 2019. Until then, please evaluate Windows Server 2019 using the Windows Insider edition, or call Microsoft support for recommendations on how to proceed.

• Windows Servers configured to “Boot from VHD” cannot be upgraded using In-place Upgrade.

Planning for In-place Upgrade

Before proceeding with In-place Upgrade, collect the following information:

• Is there a target or goal timeframe for upgrading this server?

• Is this a production-critical server?

• Is there a maintenance window for upgrading this server?

• Is there enough time for a test upgrade on an identical or similar non-production server?

• Who uses this server? Internal users, external users, or both? Have they been informed of the upgrade or maintenance?

• Is there an inventory of what is running on the server? Check the following:

  • Windows Server Roles and Features

  • Microsoft applications: SQL Server, SharePoint Server, Exchange Server, etc.

  • 3rd-Party applications: SAP, Oracle, DB2, etc.

  • Is the server joined to an Active Directory domain?

  • Are any of the server disks BitLocker protected?

  • Is the server part of a Failover Cluster?

    Note that Cluster OS Rolling Upgrade can be used to upgrade Windows Server 2016 Failover Clusters to Windows Server 2019.

• How often is the server backed-up? Have backups ever been successfully restored (applied) to the server or applications?

• What backup software is used?

• If In-place Upgrade is not successful and the server needs to be rebuilt, are the Windows Server and application install media available?

  Although it is rare, In-place Upgrade can fail and there should be a plan in-place for this possibility, to minimize server downtime and maintain SLAs.

• Is the server fully patched? It is strongly recommended that the server is fully patched prior to In-place Upgrade.

• Run systeminfo.exe and save the output:

  

• Run ipconfig /all and save the output:

  

• Run Get-WindowsFeature and save the output:

  

• Run RegEdit and capture the value of the the HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\WindowsNT\CurrentVersion hive – this will show the exact version (BuildLabEx) and edition (EditionID) of Windows Server:

  

Before proceeding with the In-place Upgrade

1. Backup the Operating System, Applications, and Virtual Machines.

2. Shutdown, Quick Migrate, or Live Migrate all Virtual Machines running on the server - Virtual Machines cannot be running on the server during In-place Upgrade.

Upgrade