Learning is a tricky thing. For both students and faculty, beliefs about learning often run contrary to an ever-growing volume of evidence in the cognitive and educational sciences. In this session, we explore the theory and practice of having students demonstrate and reflect upon their learning. Although we teach Math and Latin, two subjects which students particularly fear and loathe, the approaches and techniques we discuss can be woven into the fabric of any course. In particular, we explore how technology, both new and old, can be used to travel an evidence-based path of learning marked by peer collaboration, low-stakes, formative assessments, and carefully crafted modules.