Okay, I will try and be as thorough as possible. I’m currently running a Xubuntu host OS. Upon uploading Whonix Gateway and Workstation to Oracle VirtualBox I boot into both of them no problem. I begin the Whonixcheck and it says there is updates and upgrades for Debian, so I do “sudo apt-get update && sudo apt-get dist-upgrade” on both Gateway and Workstation. However once I’m done with the updates/upgrades I close out of Whonix and when I reopen it again the Workstation loads properly but the Gateway has a problem. The Gateway fails booting after it reaches “Begin: Running /scripts/local-block…done” it keeps repeating this line. Then it drops to initramfs. This ONLY seems to happen after the updating though. And it happens every time, I’ve reinstalled numerous times.
Which version of Whonix?
It sounds like a similar issue as described here Whonix VirtualBox 126.96.36.199.5 Testers Wanted!
though not 100% the same. In my case the boot was just delayed and it didn’t drop to an initramfs shell.
You could try the following: On the gateway after the updates have been installed but before rebooting do:
echo "RESUME=none" > /etc/initramfs-tools/conf.d/resume
update-initramfs -u -k all
Also during the upgrade look for anything odd and/or initramfs related.
New thread for this: