I'm currently trying to set up a runbook that creates a virtual machine and joins it to Azure Active Directory. While I've successfully created the VM, I'm struggling with the Azure AD join process. Every time I attempt to use the AAD login extension, it fails with the same error message. From the CommandExecution logs, I see that the DSrMDAzureHelper is failing when trying to reach the Azure metadata service at 169.254.169.254. However, when I check manually, the VM seems able to connect to that IP address just fine. The VM is located in Australia East. I've also made sure that the runbook identity has all the necessary permissions and there are no policies blocking it. It has the correct roles as well. Has anyone encountered this issue before? I really want to use the AAD extension, but I can't figure out why it can't connect to the metadata service. It's so close to working, and I just need the Azure AD join to complete the deployment.
2 Answers
Just to clarify, that 169.254.x.x IP isn't from your VM itself. It typically suggests that the VM is unable to communicate with your DHCP server, which could be the root of the connection issues. Look into your network settings and see if everything is set up correctly to ensure your VM gets assigned a valid IP address.
It sounds like you might be dealing with a networking issue. The IP 169.254.x.x is actually known as an APIPA (Automatic Private IP Addressing) address. This usually means your VM can't reach a DHCP server, indicating a network problem. Essentially, the system can't obtain a proper IP address, which is why it's not connecting to the internet or other resources. Double check your network configuration and ensure there’s a DHCP server available and functioning properly.

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