And trellis/group_vars/all/users.yml is pointing correctly to your public ssh keys? See SSH Keys | Trellis Docs | Roots . Perhaps also good to share verbose log of the provisioning of the Vagrant box. Thread https://discourse.roots.io/t/trellis-on-windows-vagrant-up-hangs-on-ssh-auth-method-private-key/8735 may also help.