Hello @websolut
Thank you for reaching out to the Microsoft Q&A platform.
The error message suggests that there's a naming conflict related to the hostnames of your Azure Virtual Machines (VMs) when trying to join them to Azure Active Directory (AAD). It is caused by the previous registration. The issue here is with Resource Cleanup. Sometimes, when VMs are destroyed and recreated, there can be delays in the release of hostnames, especially if soft-deletion is enabled for resources. Ensure that you have completely removed any previous VM instances and associated resources (NICs, storage, etc.) before deploying new VMs with the same host names.
If this is urgent, you can change the VM name to something new and redeploy the extension.
Regarding your question about elastic workloads, Azure does support elastic workloads, including VMSS cluster upgrades and re-images. However, it is important to ensure that your deployment scripts and configurations are correct and up to date to avoid issues like the one you are experiencing.
If you continue to experience issues with the AAD Windows Login extension, I recommend reaching out to Microsoft support for further assistance. They can help you troubleshoot the issue and provide guidance on how to resolve it.
If this does answer your question, please accept it as the answer as a token of appreciation.