In 2009 we presented the idea of using collaborative filtering within a complex software application to help users learn new and relevant commands (Matejka et al. 2009). This project continued to evolve and we explored the design space of a contextual software command recommender system and completed a four-week user study (Li et al. 2011). We then expanded the scope of our project by implementing CommunityCommands, a fully functional and deployable recommender system. CommunityCommands was made available as a publically available plug-in download for Autodesk‟s flagship software application AutoCAD. During a one-year period, the recommender system was used by more than 1100 AutoCAD users. In this paper, we present our system usage data and payoff. We also provide an in-depth discussion of the challenges and design issues associated with developing and deploying the front end AutoCAD plug-in and its back end system. This includes a detailed description of the issues surrounding cold...