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So... I made a major discovery.
If you want to run a OSX slave that can interact with the GUI, all you need to do is log in that user locally. Meaning, you can:
So, for the easiest configuration of an OSX slave I recommend the following:
The script at the end guarantees that the user finishes logging in locally before Jenkins will launch any jobs on the node. I suggest adding this documentation under https://wiki.jenkins-ci.org/display/JENKINS/Distributed+builds#Distributedbuilds-Differentwaysofstartingslaveagents