Making sense of algebraic expressions in context is multifaceted and extends beyond representing real-world situations using algebra. As part of Project MathTalk, the authors created videos that feature a pair of Grade 9 algebra 1 students coming to understand algebraic expressions in context. The students found three aspects of making sense of algebraic expressions challenging: (1) having quantitative meaning for arithmetic operations in algebraic expressions, (2) being able to interpret algebraic expressions from multiple perspectives, and (3) demonstrating reversibility of thought. This article is organized into three major sections--one for each aspect. In each section, the authors elaborate the mathematical idea, describe the task given to the students, and present video clips of the students encountering each challenge and making progress. Last, the authors reflect on teaching actions that support the development of each aspect of making sense of algebraic expressions in context.