Over the last two and a half years, all of us have been thrown into various forms of digital pedagogical experimentation. In this talk, we’ll explore a bit of what worked and a bit of what didn’t, as a means of thinking about ways we might expand those experiments in generative, generous ways. How might all of us continue to explore new platforms, new methods, and new collaborations? Could such exploration help us engage students not just in studying our primary subject matter but also in engaging critically with the digital tools and environments by which they are surrounded? And how might we use collective platforms like Humanities Commons both to support our own efforts and to build the shared resources needed for all of us to thrive?