Using the new release of docker-machine port (https://github.com/Parallels/docker-machine) and latest boot2docker image (1.8.1) the default settings enable time synchronization between the host and VM, however boot2docker uses UTC time and parallels does not correctly recognize this. The result is that the docker daemon on the VM refuses to allow connections because the TLS certificate is not yet valid! Going into the GUI and disabling time-synchronizating, then running "ntpclient -s -h time.nist.gov" on the VM fixes the issue.