Upgrade path from WSE 2016 to Windows Server 2019?

Question

Customer has an industry specific MIS system currently running on WSE 2016 in a workgroup - no DS. They wish to migrate to a different industry specific MIS system which claims to require a dedicated WS 2019 Standard server (physical or virtual), while still running their current system in parallel. They have one physical server with 8 cores and 24 GB.

Seems like I should make the necessary vhd(s) of the current setup, install Hyper-V, load the old system's vhd(s) in a VM, and create a second VM to house the 2019 Standard - allocating it 16GB and 4 cores to meet the new MIS system's requirements. Should just require purchase of one Windows Server 2019 Standard since Hyper-V is "free" and they would still have a valid WSE 2016 license to continue to run the old MIS until the new MIS system is fully up and running in a few months.

Where are the dragons in what I propose? What license problem have I missed? Common pitfalls of creating VHDs, installing Hyper-V, etc.?

They want it all done and dusted by next Friday - yes I know Thanksgiving is Thursday.

Answer 1

Sorry, should have also posted link to the documentation.
https://download.microsoft.com/download/7/C/E/7CED6910-C7B2-4196-8C55-208EE0B427E2/Windows_Server_2019_licensing_datasheet_EN_US.pdf

--please don't forget to upvote and Accept as answer if the reply is helpful--

Answer 2

Seems like I should make the necessary vhd(s) of the current setup

That may work out for you but also know that P2V should also be a last resort for OS deployment.

Some general info

• Each host needs to be licensed.
• A minimum of 8 core licenses is required for each physical processor and a minimum of 16 core licenses is required for each server.
• Core licenses are sold in packs of two.
• Standard Edition provides rights for up to 2 Operating System Environments or Windows Servers containers with Hyper-V isolation when all physical cores in the server are licensed. For each additional 1 or 2 VMs, all the physical cores in the server must be licensed again.

So you should be able to clean install the host, patch fully, add hyper-v role stand up the two virtual machines mentioned.

--please don't forget to upvote and Accept as answer if the reply is helpful--

Answer 3

After running numbers and checking with the new vendor for the real, verses published, requirements, I've decided to do an in-place upgrade of WSE2016 to WSE2019 first. I'm pretty sure the old and new systems can co-exist for the month or two before we go live with the new MIS system. Until that happens, the load on the new system will be system setup and data conversion, which can be done in off-hours. If WSS2019 proves necessary, I plan to side-upgrade the WSE2019 to WSS2019 in-place but would prefer to avoid the cost of Standard and the 20+ CALs since we'll be below the 25 user / 50 device limits of Essentials. If we need two or more VMs, MS drops Essentials, or our MIS vendor forces it, we'll move to Standard next year.