I’ve long (i.e. always) had problems with Docker Machine and VMWare Fusion - the machine creation would hang, ever awaiting a live network, and I’d end up throwing my toys and returning to VirtualBox.

Luckily, it appears I was far from alone and Mark Bainter came up with a set of actions that have cured the problem for me on two machines now:

docker-machine delete dev # or as appropriate
brew cask uninstall vmware-fusion # or trash it from /Applications
sudo rm -rf \
  /opt/homebrew-cask/Caskroom/vmware-fusion \
  /opt/boxen/homebrew/bin/vm* ~/.docker \
  /var/root/.docker

At this point reboot (or not if you’re feeling brave), download Fusion from VMWare’s site, install normally and kick off a new machine: docker-machine -D create --driver vmwarefusion --vmwarefusion-memory-size 4096 --vmwarefusion-cpu-count 1 dev

And hopefully celebrate success!