Hello Joshua
Welcome to Microsoft Q&A Platform, thanks for posting your query here.
Please try these troubleshooting steps:
-Try to stop and then start the VM, the stop causes the VM to be deallocated (which a reboot doesn't) - mostly this will resolve the issue.
-Check if the VM agent is running on the virtual machine. You can do this by logging into the virtual machine and checking if the Windows Azure Guest Agent service is running. If it is not running, try starting the service manually.
-You can try uninstalling and reinstalling the VM agent.
Refer to this troubleshooting document:
https://learn.microsoft.com/en-us/troubleshoot/azure/virtual-machines/windows-azure-guest-agent
Hope this helps.