Issues installing Docker on OS 10.10 or later?

Today I was trying to install the Docker Toolbox on my Mac. It failed. Because I was able to fix it and did not see any other articles on how to do this that specifically referenced this app or issue, I decided to write it up. Because, community!


The installation appeared to work fine, but once I clicked the “Docker Terminal” icon, the terminal would launch with the following message:

Docker Machine is not installed. Please re-run the Toolbox Installer and try again.

Docker Machine installs by default to the /usr/local/bin directory in OS X. And when I tried to change that location in the install package, I didn’t have any luck.

That directory is locked down pretty tight (700 permissions, my user as the owner).

drwx------  24 parisi  wheel  816 Mar 25 10:52 bin

When I tried to open the directory up a bit and re-install, it would have the same issue. And, when I tried to cd directly into that directory, it either threw a permission denied or silently failed, even though I had allowed access:

$ sudo chmod 766 bin

$ ls -la
total 0
drwxr-xr-x   5 root    wheel  170 Mar 25 10:50 .
drwxr-xr-x@ 10 root    wheel  340 May  8  2015 ..
drwxr-xr-x   3 root    wheel  102 Apr 20  2015 Qt
drwxrw-rw-  24 parisi  wheel  816 Mar 25 10:52 bin
drwxr-xr-x   3 root    wheel  102 Mar 25 10:50 share

$ cd bin
-bash: cd: bin: Permission denied

$ sudo cd bin

$ pwd

And Docker commands failed:

$ docker
-bash: docker: command not found

Color me stumped.

So I turned to Google and found an article on Homebrew installations failing, but nothing specifically on Docker failing. I used the Homebrew workaround found in this article and it fixed my issue.

Here are the commands I ran:

$ sudo chown $(whoami):admin /usr/local && sudo chown -R $(whoami):admin /usr/local

Essentially, the command above does a recursive (-R) chown on the /usr/local directories as the logged in user (via whoami).

Before the change, /usr/local looked like this:

drwxr-xr-x     6 root  wheel    204 Mar 25 10:56 local

After the change:

drwxr-xr-x     6 parisi  admin    204 Mar 25 10:56 local

After that, I could run Docker commands:

$ pwd

$ docker
Usage: docker [OPTIONS] COMMAND [arg...]
       docker [ --help | -v | --version ]
A self-sufficient runtime for containers.

  --config=~/.docker              Location of client config files
  -D, --debug                     Enable debug mode
  -H, --host=[]                   Daemon socket(s) to connect to
  -h, --help                      Print usage
  -l, --log-level=info            Set the logging level
  --tls                           Use TLS; implied by --tlsverify
  --tlscacert=~/.docker/ca.pem    Trust certs signed only by this CA
  --tlscert=~/.docker/cert.pem    Path to TLS certificate file
  --tlskey=~/.docker/key.pem      Path to TLS key file
  --tlsverify                     Use TLS and verify the remote
  -v, --version                   Print version information and quit


And the Docker terminal starts correctly:

Creating CA: /Users/parisi/.docker/machine/certs/ca.pem
Creating client certificate: /Users/parisi/.docker/machine/certs/cert.pem
Running pre-create checks...
Creating machine...
(default) Copying /Users/parisi/.docker/machine/cache/boot2docker.iso to /Users/parisi/.docker/machine/machines/default/boot2docker.iso...
(default) Creating VirtualBox VM...
(default) Creating SSH key...
(default) Starting the VM...
(default) Check network to re-create if needed...
(default) Found a new host-only adapter: "vboxnet0"
(default) Waiting for an IP...
Waiting for machine to be running, this may take a few minutes...
Detecting operating system of created instance...
Waiting for SSH to be available...
Detecting the provisioner...
Provisioning with boot2docker...
Copying certs to the local machine directory...
Copying certs to the remote machine...
Setting Docker configuration on the remote daemon...
Checking connection to Docker...
Docker is up and running!
To see how to connect your Docker Client to the Docker Engine running on this virtual machine, run: /usr/local/bin/docker-machine env default

                        ##         .
                  ## ## ##        ==
               ## ## ## ## ##    ===
           /"""""""""""""""""\___/ ===
      ~~~ {~~ ~~~~ ~~~ ~~~~ ~~~ ~ /  ===- ~~~
           \______ o           __/
             \    \         __/

docker is configured to use the default machine with IP X.X.X.X
For help getting started, check out the docs at

If you’re interested on more detail on the issue, check out the Homebrew blog, as well as this on System Integrity Protector (SIP):

Hopefully this helps someone else.

Another option, pointed out to me on Twitter, is to use the native Docker apps (still in beta):

If interested, I’ve written a couple other blogs on Docker.

TECH::Using NFS with Docker – Where does it fit in?

TECH::Docker + CIFS/SMB? That’s unpossible!


2 thoughts on “Issues installing Docker on OS 10.10 or later?

  1. Pingback: TECH::Using NFS with Docker – Where does it fit in? | Why Is The Internet Broken?

  2. Pingback: Is this blog a Top vBlog 2016? | Why Is The Internet Broken?

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