This session is intended for instructors interested in the complexity of understanding what students know and can do. Participants will consider the challenge of assessing students accurately and embracing the ambiguity inherent in making judgments about the knowledge and skills of other people. Classical test theory tells us that the scores we observe in the test results of our students are the sum of their true ability and some amount of undefined error, which has implications for the judgments we make. Expanding this principle to assessments broadly, participants will consider three key questions: 1. Why do we assess students? 2. What are potential sources of error in understanding what students know and can do? 3. What is the role of fairness, equity, and equality in assessing individual students? 4. How can we acknowledge these sources of error and support our students? Student self-evaluation and instructor/student conversations will be presented as techniques that may help us better understand the learning of our students. This session will engage participants in assessment theory, the role of error, concepts of reliability and validity in assessment, and ultimately lead to a broader dialogue about how we engage in understanding student learning in our classes.