Started machine on mac, Notice both machines stared with the same IP!
I was not able to reproduce the issues as of now.
Using toolbox 1.9.0 on El Captain
➜ ~ docker-machine ls
NAME ACTIVE DRIVER STATE URL SWARM
dashboard - virtualbox Running tcp://192.168.99.100:2376
default - virtualbox Running tcp://192.168.99.100:2376
Stopped and restarted them and they got different its:
NAME ACTIVE DRIVER STATE URL SWARM
dashboard - virtualbox Running tcp://192.168.99.100:2376
default - virtualbox Running tcp://192.168.99.101:2376