Windows as a Service cheat sheet

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It’s been three years since I worked in Windows marketing talking about Windows as a Service. At the time, I was quite happy to say that I would never have to talk about WaaS again. Well, you can never really escape that conversation, you can just do your best to avoid it. Now, I don’t even mind…

I’ve seen some questions recently about how the latest announcements about the 21H1 release of Windows should be considered. But really you should be looking more broadly, depending on what release you are currently running and how much time is left on that release. The Windows 10 release information page remains the authoritative source that everyone should be following, but here’s a quick take projecting that forward with (a) the new 21H1 release details, and (b) the expected 21H2 full release:

If you are running an Enterprise SKU of…	You should …
Something earlier than Windows 10 1803	Seek help. You’re already unsupported.
Windows 10 1803 or 1809	Hurry up and deploy at least Windows 10 2004. You only have until May 11, 2021.
Windows 10 1903	This is already unsupported. Install the Windows 10 1909 enablement package right now, so that you are again supported.
Windows 10 1909	This is supported until May 10, 2022. You should deploy Windows 10 2004, 20H2, or 21H1 as a full feature update (my vote would be for 20H2 because you’ll be scared of 21H1 being “too new”), starting somewhere around or before May 2021 to give yourself at least a year to complete the process. Don’t wait for 21H2 as that won’t leave you enough time to safely upgrade.
Windows 10 2004	This is supported until December 14, 2021. Install the Windows 10 20H2 enablement package by then.
Windows 10 20H2	This is supported until May 9th, 2023. You’ve got plenty of time. Installing the Windows 10 21H1 enablement package won’t change that date any (if we assume a release of April 13, 2021 + 18 months, that’s still before May 9th 2023). Look to deploy 21H2 or 22H1 (probably 21H2) by May 2022.
Any LTSC/LTSB release	You didn’t listen to me before, so I don’t expect you to start now. You’re on your own. Remember you can upgrade from LTSC to a semi-annual channel release at any time, just needs to be a newer build number.

A few general comments:

Enablement packages should be fairly safe to deploy (following a controlled rollout process), since they just turn on features that were otherwise hidden when you installed previous cumulative updates. The real risk is with those cumulative updates…
Tanium fully supports deploying feature updates and enablement packages using the Deploy and Patch solutions. For feature updates, you can deploy an initial compatibility scan to detect issues, then use the results of that detection for targeting later. See here for more process details.