Hi Chris,
Hope you're doing well.
Are there any errors when the issue occurs?
Please review the Windows Event Viewer on the virtual machine for any disk-related errors or warnings during the reboot. If possible, please provide me the screenshots. Thanks.
Then, verify the settings for the secondary hard drive in the VM configuration in VMware. Ensure that the hard drive is correctly added and configured. Pay attention to the controller type (e.g., SCSI, SATA) and other relevant settings.
Verify that there are no disk signature conflicts between the primary and secondary hard drives. If there is a conflict, it can cause Windows to treat the disks as the same, leading to connectivity issues.
Best Regards