Hi @Rising Flight
Welcome to the Microsoft Q&A Platform! Thank you for asking your question here.
Microsoft fully supports custom images in Azure. Once you configure your Windows Server VM with the desired configuration and security settings, you can convert it to your desired image. This image can then be used to deploy new VMs with consistent configuration, helping to standardize your environment.
Azure Update Management is the recommended way to manage Windows updates on your VMs. First, create an Automation Account in the Azure portal, enable Update Management, and connect your VMs to it. Once configured, you can schedule updates manually and check for any missing or failed updates in your environment.
Azure Update Management will notify you if the update fails. You can try running the built-in Windows Update Troubleshooter on the VM first to troubleshoot common problems. If that doesn't work, check the Event Viewer for error information. In some cases, you may need to manually download and update information from the Microsoft Update Catalog.
If you have any further queries, do let us know
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