This talk presents the efforts and results of porting Vagrant to OpenBSD by writing a plugin that uses vmd(8) as a 'provider' to create and manage OpenBSD VMs and to properly detect OpenBSD as a host system and expose the needed capabilities, most notably NFS to exchange data between host and guest. With such a localized environment it becomes easy and straightforward to develop, test and run automated installations of OpenBSD within the VM guests. The talk will show how this is done under different objectives and prerequisites like per-VM, per-Location, etc. customization while installing over a dozen (or 100) VMs fully automated in parallel while minimizing the effort to do so.