Upgrade Windows Server 2008 R2 to Windows Server 2019

Planning for In-place Upgrade

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

Is there a target or goal time-frame 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 Failover Clusters have separate migration options.

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.