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Dear Nathan,
The error "The Virtual Machine is undergoing a reboot due to a guest OS crash" indicates that the guest operating system is crashing repeatedly, causing automatic reboots that eventually fail.
- Check serial console or boot diagnostics for kernel panic or BSOD messages.
- Boot into Safe Mode / Recovery (use Serial Console or capture the OS disk and mount to another VM).
- Review recent updates – Roll back if a patch or config change occurred.
- Check VM Agent logs – Some crashes are triggered by corrupt agents.
- Create a support ticket if you're on Azure and need backend investigation (especially for platform-side issues).
Best Regards,