We're currently having issues getting USB passthrough of the programmer to work properly through VirtualBox. See ELEC-405 - Getting issue details... STATUS  for context. Since the SSH solution can be done in a shell script, I'm documenting the process here.

Setup

You should already have set up your Vagrant box as specified in Setup.

1. Save the following as macos.sh.

   macos.sh

   #!/usr/bin/env bash
   
   # Disable USB filters - you may need to manually remove them
   sed -i -e 's:BetterUSB.usbfilter_add:# BetterUSB.usbfilter_add:g' Vagrantfile
   vagrant reload
   
   # Build and install setsid
   git clone https://github.com/tzvetkoff/setsid-macosx.git
   make -C setsid-macosx
   mv setsid-macosx/setsid /usr/local/bin
   rm -rf setsid-macosx
   
   # Install brew non-interactively - copied from https://brew.sh/
   ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)" < /dev/null
   brew install openocd
   brew install make
   brew install minicom
   # Install gcc-arm-embedded 6-2017-q2-update (gcc7 segfaults)
   brew cask install https://raw.githubusercontent.com/caskroom/homebrew-cask/4d16a06d09bc695c6a7252843106c5d7adce5877/Casks/gcc-arm-embedded.rb
   
   # Generate SSH keypair and copy the public key into the host
   vagrant ssh -c "cat /dev/zero | ssh-keygen -q -N '' && echo 'Generated SSH keypair'"
   vagrant ssh -c 'cat ~/.ssh/id_rsa.pub' >> ~/.ssh/authorized_keys
   
   # Disable password authentication on host SSH server for safety, then enable Remote Login (SSH)
   sudo sh -c "sed -i -e 's:#PermitRootLogin prohibit-password:PermitRootLogin no:g' /etc/ssh/sshd_config \
   && sed -i -e 's:#PasswordAuthentication yes:PasswordAuthentication no:g' /etc/ssh/sshd_config \
   && sed -i -e 's:#ChallengeResponseAuthentication yes:ChallengeResponseAuthentication no:g' /etc/ssh/sshd_config \
   && sed -i -e 's:UsePAM yes:UsePAM no:g' /etc/ssh/sshd_config \
   && systemsetup -setremotelogin on"
   
   # Add environment variables so we can SSH from the guest
   vagrant ssh -c "echo 'export MACOS_SSH_USERNAME=\"$(whoami)\"' >> ~/.bashrc"
   vagrant ssh -c "echo 'export MACOS_SSH_BOX_PATH=\"$(pwd)\"' >> ~/.bashrc"
   # Switch OpenOCD script dir since it's different when installed by brew
   echo "export OPENOCD_SCRIPT_DIR=/usr/local/share/openocd/scripts/" >> ~/.bashrc
   
   # Set up paths and add a .bash_profile for SSH
   echo "[[ -f ~/.bashrc ]] && source ~/.bashrc" >> ~/.bash_profile
   echo 'export PATH="/usr/local/bin:/usr/local/opt/make/libexec/gnubin:$PATH' >> ~/.bashrc
   source ~/.bashrc

2. Run the following in your terminal:

   macOS Terminal

   # Move to your box directory
   # cd ~/box
   ./macos.sh