Upgrading On-Premise Server OS now or after Azure Migration?

[PATRY THACH]

Hello,

We have some old VMWares that are running Windows Server 2008 that have already been setup for ASR on Azure, but we now need to upgrade this server OS to Server 2019. We also plan on migrating to Azure by the end of this year. 

Should we upgrade the VMWare now or upgrade it after we fully migrate to Azure? How does this affect licensing of the OS?

I'm not exactly sure what needs to be done first.

Thanks in advance for your input and suggestions.

[#2]

Hi@PATRY THACH 

I would say do it and use "Azure Site Recovery"

Below will help you

https://docs.microsoft.com/en-us/azure/site-recovery/migrate-tutorial-on-premises-azure

You can move to Azure anytime , check this out https://azure.microsoft.com/en-us/overview/azure-vmware/

[#3]

Thanks for the helpful links!

So, how would it affect our licensing though? If we purchase new license to upgrade our OS for the on-premise VM. Would we need to purchase a new license (again) for the Azure VM once we migrate?

[#4]

Hi@PATRY THACH 

Your welcome.

When you create your VM on Azure it will ask you below option :)

If you don't have the license Just say no and it will provide you a VM with license as part of the hourly price. You won't pay for license to have it , it is with the VM.

[#5]

Something to keep in mind is that the on premise licence requires that software assurance is purchased if you plan to move it to Azure and utilize the Azure Hybrid Use benefit. You can also as an alternative buy the licence through CSP in a 1 or 3 year term. It is based on cores and can really end up saving your organization quite a bit since the OS cost is calculated in the hourly consumption.   @Deleted 

[#6]

Okay, good to know!

[#7]

Thanks, Bryan! Good to know!