I was able to talk to Docker from the OS X command shell. Once I removed that firewall rule with: sudo ipfw delete 00411 I checked the firewall rules, and sure enough a new rule was added. Sure enough, once I fired up my VPN, I got the following (different) error. Uninstall all those broken versions of MySQL and re-install it with Brew on Mac Mavericks 295K 46 Mac OS X: ValueError: unknown locale: UTF-8 in Python 174.7K 13 Determine OS X version from the command line 126.

So, without VPN fired up I looked for this rule, and it was not there. It suggested to look for a firewall rule that denies any to any. But the insightful bit was 'Connecting to VPN Things will break'. I read through it in detail, but I think most of what he is suggesting in the first part has been factored into the most recent version of boot2docker. I found this post by Florian Rosenberg useful. I rebooted my machine, and started with Docker from the beginning.

Today, thanks to a colleague's suggestion, I did not startup my VPN connection first. This happened to me as well, and none of the previous answers fixed the problem. I have verified that Docker is running inside the boot2docker VM and that my port is correct. I get a timeout error message when I run Docker even though the boot2docker VM is running in the background.

I'm running Mac OS 10.9.5 (Mavericks), I've followed to install Docker.

Docker mac os x mavericks