Knowledge Base Article

Windows Server 2019 Setup

Setup Windows Server 2019 with specifics for upgrades and virtualization.


Last Review: May 29, 2019

Product(s): Windows Server 2019

Author(s): John Whinery


A cyberist created this article using the patented Delta Method by modernizing a typical approach.


These are best practice procedures for installing or upgrading Windows Server 2019 precautions, known issues, and testing.


All requirements should be verified before proceeding to implementation steps:

  • Windows Server 2019 only allows in-place upgrade for Datacenter (HyperV) machines. Other physical and virtual servers require clean install with setup of applications or services and migration of data.
  • Local administrator password must be verified or reset if unknown in case you must log into the local machine and rejoin to the domain. Domain administrator credentials are required to join a domain or for global network permissions.
  • IP addresses must be recorded if settings aren't retained and to avoid conflicts or replicate settings on other servers.
  • Backup of physical server should be performed and export of virtual machines locally and on another host is recommended.
  • Eventviewer errors, legacy apps or third-party anti-virus, and hardware firmware should all be removed or updated prior to performaing an upgrade.
  • Internet connection is required download and ISO and perform Windows Updates.
  • Dual layer DVD is required to burn an ISO of Windows Server 2019 and the license key must be documented before installation.
  • Installation takes approximately 60 to 90 minutes depending upon physical or virtual server and the speed of the machine, not including configuration, updates, and application setup.
  • System and data should be split and all volumes should be formated before configuring roles or installing applications.
  • Interface order must be set on all network cards and unused cards should be disabled. Firewall should always be on and IPV6 enabled and DNS ::1 removed.
  • License Activation will often fail and usually must be done in PowerShell as outlined below.
  • Dell Server Administrator or similar manufacturer tool should be installed after setup to check for any hardware firmware or drivers that must be updated before running Windows Updates.


  1. Log into or boot the server to setup as an administrator by inserting the DVD or double-clicking the ISO and running Setup.
  2. Select Standard/Desktop Experience in most cases so you get a full GUI and Datacenter/Desktop Experience only for Hyperv hosts.
  3. Save Files and Folders, start the install and the server will restart several times.
  4. Activate licensing after first logon by opening PowerShell and entering: slmgr.vbs /ipk licensekeywithdashes


Check for any Event Viewer errors and test functionsor applications with user verification. Processor or RAM may need to be increased for better performance depending upon Hyperv or virtual machine workload. Any backup or virtual machine export of previous OS after upgrade may now be deleted.