Hi @Michael Gilleran ,
Thank you for posting in Microsoft Q&A forum.
For the question, the clients need to contact CM via VPN at 10pm on Friday, otherwise they will not be triggered to download the updates from Microsoft .
So yes, if we want to deploy the updates via VPN, the clients need to be connected to VPN at the time that the deployment is scheduled.
If you don't want to connected to VPN for such a long time, we could set one of the client in the boundary group as a DP, then deploy the update contents to this DP and let the other clients access it to download the contents.
Hope the above information can help you.
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