With the advent of Moodle 2.X and Moodle HQs commitment to provide major dot point upgrades every six months, institutions need to have a very clear plan in place to ensure they stay current with the technology. Organisations cannot afford to get too far behind with a product that is evolving so quickly. The University of Southern Queensland (USQ) that self hosts three major instances of Moodle (USQStudyDesk, USQStaffDesk and USQOpenDesk) has committed itself to roll with a six-monthly upgrade cycle, aligned with its two major teaching periods. To do this we have developed a robust methodology and testing schema to ensure we meet our targets and commitments to the many key stakeholders involved. In July 2012 USQ upgraded from 1.9 to 2.2, in February 2013 it went to 2.3 and in June to 2.4, etc., etc. This is not a light undertaking and this presentation will share what USQ has had to do to ready itself for this type of commitment. Having now done this three times this presentation will look at some of the lessons learned. It will posit a series of considerations and look at the implications on ICT staff, systems support staff, training staff and more importantly, what this means for the consumers; academic staff and their students.