I recently had need of an circa 2000 Windows CD-ROM. It was a language learning CD-ROM, and I wanted to run it in a VirtualBox VM running Windows XP.

My main machine is a MacBook Air. I don’t have an external optical drive, so I also wanted a readable image. I have another Mac with an optical drive to do the initial read.

To mount the drive

> mkdir /Volumes/foo
> mount_cd9660 -er /dev/disk1s1 /Volumes/foo

To make a image of it that’s readable in a Windows VM

> hdiutil makehybrid -o /tmp/foo.iso /Volumes/foo

Note, don’t use Disk Utility.

The resulting file can be mounted and read by the XP machine.