On June 13, 2011, after more than 21 years, 115 thousand orbits, and nearly 1 million exposures taken, the operation of the Hubble Space Telescope successfully transitioned from 24x7x365 staffing to 815 staffing. This required the automation of routine mission operations including telemetry and forward link acquisition, data dumping and solid-state recorder management, stored command loading, and health and safety monitoring of both the observatory and the HST Ground System. These changes were driven by budget reductions, and required ground system and onboard spacecraft enhancements across the entire operations spectrum, from planning and scheduling systems to payload flight software. Changes in personnel and staffing were required in order to adapt to the new roles and responsibilities required in the new automated operations era. This paper will provide a high level overview of the obstacles to automating nominal HST mission operations, both technical and cultural, and how those obstacles were overcome