Connecting to Docker Running on Mac Server

Expected behavior

I tried to set up the Docker application on both my laptop and a Mac Mini server that I have, and then add the server as a machine in docker-machine. I’ve been trying to get it working with the generic driver, but am so far unsuccessful. I executed:

$ docker-machine create \
--driver generic \
--generic-ip-address=my.domain.name \
--generic-ssh=user=$USER \
my_server

And was expecting to be able to add it as a machine that I could point my local environment at. While I’m sure this is by no means something that is intended for production, I thought that it might be a nice way to throw little tests or example apps up on a server from my local machine in an easy way, since I could develop it in Docker locally and then just point my environment at my server and deploy it to there.

Actual behavior

I ran into two different errors:

The first occurs if I run the exact command above; I see this output:

Creating machine...
(my_server) No SSH key specified. Connecting to this machine now and in the future will require the ssh agent to contain the appropriate key.
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...
Error creating machine: Error detecting OS: Error getting SSH command: Something went wrong running an SSH command!
command : cat /etc/os-release
err     : exit status 1
output  : cat: /etc/os-release: No such file or directory

If I specify the path to my SSH key, it just hangs forever, “Waiting for SSH to be available”

Information

Diagnostic output:

OS X: version 10.11.5 (build: 15F18b)
Docker.app: version v1.11.0-beta7
Running diagnostic tests:
[OK]      docker-cli
[OK]      Moby booted
[OK]      driver.amd64-linux
[OK]      vmnetd
[OK]      osxfs
[OK]      db
[OK]      slirp
[OK]      menubar
[OK]      environment
[OK]      Docker
[OK]      VT-x
Docker logs are being collected into /tmp/20160414-180638.tar.gz
Most specific failure is: No error was detected
Your unique id is: 57B846BA-9DCD-4E33-8E91-DB0AE38E97E2
Please quote this in all correspondence.

Other info: