Failure to establish connection when provisioning via ansible-playbook server.yml

[fullyint]

There are many possible causes for UNREACHABLE but here’s one that comes to mind:

UNREACHABLE - Error on Initial Provision

The Trellis README mentions that it configures a server with Ubuntu 14.04. Could you check that your droplet is running 14.04? There is progress toward moving to 16.04 soon. But if you try to provision a 16.04 droplet currently, you will likely get the error in your output above: /usr/bin/python: not found.

If you are in fact using an Ubuntu 14.04 server, could you run your command again and share the full debug info?

ansible-playbook server.yml -e env=staging -vvvv