Between September 2007 and August 2014, more than 100,000 University of Waterloo students completed an assignment inside of Maple T.A. This number continues to grow exponentially as we work with Maplesoft to improve our fully online and blended courses, develop high school outreach resources, move some of our online math courses to an open space, and create a content authoring tool specifically targeted to those in a STEM-related discipline. This presentation will summarize how we transform ideas into tangible learning objects and discuss some of the implementation challenges we've encountered and overcome (or encountered and are still trying to overcome) over the years.