So we had to reboot the system pressing cmd r so you go into a troubleshooting system and not the normal OS environment. Problem is these files cannot be deleted even using sudo. Using the terminal to search for files with virtualbox in the name of the file, we found (non vagrant related) files that were still in the system. The issue is related to the system not deleting all files from the virtual box installation. Ok, this is a bit of a hassle but we did manage to make it kind of work. Run brew cask reinstall -force virtualbox Keep approving the kexts until the script runs cleanly: Run this script after you attempt to install virtualbox. Sudo kextload "/Library/Application Support/VirtualBox/VBoxUSB.kext" -r "/Library/Application Support/VirtualBox/" Sudo kextload "/Library/Application Support/VirtualBox/VBoxNetFlt.kext" -r "/Library/Application Support/VirtualBox/" Sudo kextload "/Library/Application Support/VirtualBox/VBoxNetAdp.kext" -r "/Library/Application Support/VirtualBox/" Sudo kextload "/Library/Application Support/VirtualBox/VBoxDrv.kext" -r "/Library/Application Support/VirtualBox/" Kextstat | grep "" > /dev/null 2>
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