On Friday, June 22, Hybrid Pedagogy hosted a discussion on Twitter focused on the relationship between pedagogy and technology, and the relationship between teachers and technologists. We set out with the intention of mining the relationships for possibilities, potentials, but also for weaknesses and shortcomings. At the center of our conversation sat the LMS (Learning Management System), the bane and boon of online and hybrid teaching. For many, the LMS is an unusable educational tool, while for others it is a technology ripe for the hacking. But some technologists believe the LMS is a work in progress, and may well be the future of educational technology. We invited Jared Stein of Instructure, the makers of the Canvas LMS, and some of their customers to join our discussion.