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are you using kms

We are Azure-based, so I believe so, yes... Some of the other VDAs that HAVE activated have Registry entries in them that say something like "kms.core.windows.net"

if its active directory based kms then no need to rearm

So just run slmgr /ipk <product key> (from that web page) on my BASE Image, make a new Snap, and then I'm good when I update my Catalog from the new Snap?

it should work

I'll try it and post back the results, in case this helps someone else

If azure based follow this - Depending on how the routes are configured traffic could be blocked to get to Azure KMS service. This guide talks through options and troubleshooting tactics to get to root of the issue, and you can pass along to your network team to create a route, or open destination address/port https://docs.microsoft.com/en-us/troubleshoot/azure/virtual-machines/troubleshoot-activation-problems

OK I think we figured it out: The Master Image needs a GVLK configured on it, which is then seen by the KMS Host Server when Domain Join happens (as part of MCS provisioning), and that triggers a permanent Volume License Key assignment to each of the new VDAs... Read all about it here: https://docs.microsoft.com/en-us/windows-server/get-started/kms-client-activation-keys