Hello @matt sanders,
If your VM remains stuck in the "Updating" status, start by restarting it via the Azure Portal or using PowerShell commands to refresh its state. If the problem persists, check for potential disk space issues or try removing specific directories related to the VM's extensions before restarting the agent.
A Windows VM doesn't start. When you check the screenshots in the Boot diagnostics window, you see that the startup is stuck in the update process.
Depending on the number of updates that are getting installed or rolled backing, the update process can take a while. Leave the VM in this state for 8 hours. If the VM is still in this state after that period, restart the VM from the Azure portal, and see if it can start normally. If this step doesn't work, try the following solution- https://learn.microsoft.com/en-us/troubleshoot/azure/virtual-machines/windows/troubleshoot-stuck-updating-boot-error?source=recommendations
I would recommend check the logs and metrics to identify any specific errors or issues that could be causing the VMs to be stuck in an unknown or updating state.
If you have any further queries, do let us know.