After years of noticing the challenge our students have with fraction operations, we decided to implement a scaffold approach that focuses on using benchmarks to better develop both students' understanding of a fraction as a quantity and their ability to think about fraction operations meaningfully. While we found this approach supported students in making sense of fraction addition, we also found that students did not always respond as anticipated. This led to rich discussions tied to important mathematical ideas related to fractions and fraction operations, for example, the importance of the whole and reasonableness of a solution. We showcase student thinking in response to the provided tasks and offer teaching insights to help aid students in making sense of fraction magnitude and operations using benchmarks in mathematics classrooms.