Operating Systems

Windows Server 2019 on VMWare

When installing an evaluation image of Windows Server 2019 in VMWare Workstation Player, there is an error that can occur during initial installation.

Following this guide from Joshua Caulfield mostly resolved the issues for me, however I slightly changed 2 steps.

How to install Windows Server 2019 in a VM with VMWare | by Joshua Caulfield | CertiFried IT | Medium

  1. Create the virtual machine and select the Windows_Server_2019.iso file to load onto the disk.
  2. Start the machine after all the settings and resources have been allocated.
  3. Once the GUI appears for the installation screen, Power Off the virtual machine.
  4. Go into the Virtual Machine Settings, and find the tab for Hardware.
  5. In this tab, there should now be a device labeled Floppy.
  6. Click on the Floppy device option and find the check box that says Connect at power on.
  7. Uncheck this box, but do not delete the Floppy device.
  8. While in this menu, you can also now click the Add button at the bottom to add a new CD/DVD Drive.
  9. Go to the newly added CD/DVD Drive device and Use ISO image file for the VMWare_Tools.iso
  10. Start the virtual machine again and go through the installation process.
  11. Once installation is complete, open This Computer and find the DVD for VMWare Tools on the virtual machine.
  12. Install VMWare Tools by running the executable and it should resolve the resolution issues and add more functionality.
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