Boxplots are statistical representations for organizing and displaying data that are relatively easy to create with a five-number summary. However, boxplots are not as easy to understand, interpret, or connect with other statistical representations of the same data. We worked at two different schools with 259 middle school students who constructed and interpreted boxplots. We observed that even students who were able to create boxplots had difficulty interpreting data represented in a boxplot. After sharing specific difficulties that we observed students having, we discuss ways to help students to make sense of data presented in boxplots.