Inspired by the visionary backdrop of Dr. Roper’s “There is no Spoon” and the solid framework of transformational guidance captured in the DoD Digital Engineering Strategy, the US Air Force has started its journey of digital transformation.  With an enterprise spanning everything from science and technology creation to fleet retirement and disposal, accomplished over a product lifecycle that can last 100 years, this endeavor faces unprecedented complexity and innumerable challenges, especially where single, uniform answers are rare (and sometimes dangerous).  This presentation highlights a philosophy of experimentation as a means of the AF achieving its primary objectives, and will include examples of past and ongoing efforts that utilize flexible technology platforms to address data challenges, culture change, and process reengineering risks.