Safely upgrade Workstation from very old version

[EJEgan]

Apologies, not VMware fluent. I have a client with an old VMware Workstation version 9 installation, supporting a Linux based ancient ADP database VM. This is on a Windows 10 Pro (i5, 8GB, 250GB SSD) host that will no longer update until VMware is brought more current.

As I understand it, an new purchase is needed, not Upgrade pricing; that's not an issue. I'm just looking for guidance on the best way to upgrade the existing configuration from 9 to 15.5 without issues. Do I uninstall 9 and fresh install 15.5, or will 15.5 find what it needs to intelligently if I just run the installer?

Support for this ancient VM is non-existent, so I'm sweating a little.

TIA

[daphnissov]

The best approach is to take a full backup of this system prior to any upgrade activities, especially since this is (likely a high profile) ADP. That way, if an in-place upgrade fails and the VM cannot be brought back into service, you have a full backup of the system. Also take a separate backup of the VM when it is powered off. A copy-and-paste to something like an external USB drive often does the job. I don't know if an in-place upgrade from 9 => 15.5 works or not, but with that large a gap I might just uninstall 9 and install 15.5 fresh, again doing those two separate tasks I listed first.

[Mits2020]

I find daphnissov​'s advice very careful and sound - the #1 principle is to never mess with/upgrade a production system, especially when there is only one instance of it. I am sure you can find a second PC/laptop and do all the experiments in that: Install your desired OS and Workstation version, copy the Linux VM there and try booting it. If it doesn't work, you can afford experimenting with that 2nd PC until you find the cause. The first system will always be there, working at it always has.

[RDPetruska]

Just to add - make sure the VM guest is powered off (not suspended, including to the guest OS itself - use any shutdown menu it has) before doing the upgrade.

After backing up, and upgrading Workstation - on the initial VM power up, I would not allow the virtual hardware upgrade at first.  Boot it up as is, and test things out.  If all works, and you don't need any newer functionality, I would leave the virtual hardware (Workstation compatibility) alone.  You can always make a copy and upgrade that to test later.