Would it run on an Apple / could it run on a new Apple? https://www.dosbox.com/wiki/DOSBox_and_Mac_OS_X Mine (Linux) runs dosbox.conf when you run the dosbox command, and I've edited my dosbox.conf [autoexec] section to include mount C /mnt/sda2/DOSBox-Win31-Newport/C i.e. the mount command (going by the above wiki, on mac it might look something like MOUNT C ~/DOSGAMES (using their choice of directory/folder)) and at the very end of dosbox.conf I have CALL WINDOWS.BAT that starts Win3.1, which is set to auto start Newport.