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I have an Azure VM that was created with the OS included in the price. Is it possible to upgrade the same VM to a newer OS (e.g. one that would also be included in the VM price)?

Specifically, I would like to upgrade from Windows Server 2012 R2 Datacenter to Windows Server 2019 Datacenter.

If it is possible, how do you do it?

Thanks!

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  • AFAIK upgrading Windows isn't supported in Azure; you're meant to start a new VM and migrate your workload to it.
    – Michael Hampton
    Nov 9, 2018 at 2:16

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An in-place system upgrade is not supported on Windows-based Azure VMs, below is a link to the officially statement and some options if you REALLY need to go that route.

https://support.microsoft.com/en-us/help/4014997/an-in-place-system-upgrade-is-not-supported-on-windows-based-azure-vms

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No, Aside from upgrades not being supported, there is really not much reason to upgrade an Azure VM since you can simply build a new one and install your app (probably) far faster than an upgrade would take.

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  • Maybe you can. We are installing a 3rd-party app that also needs a bunch of other ancillary software installed and additional configuration. It takes about 2 days to set everything up. Besides, if you had a modern .NET web app (without a bunch of legacy ActiveX cruft) it would make more sense to just use Azure PaaS instead of messing around with VMs. :-)
    – taraz
    Jan 29, 2019 at 22:26
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    @user228546 understood, take a look at using DSC or ARM templates to deploy your software and configs to cut down deployment time.
    – Jim B
    Jan 30, 2019 at 19:52
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I did manage to upgrade in-place some of my Azure VMs, summarized it here for future reference: https://www.mattiasdesmet.be/2020/04/26/upgrade-the-azure-vm-windows-os/

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