The benefits of student engagement with real-world contexts seem to be
well accepted by the mathematical modelling and application ‘community’. Yet concerns related to difficulties necessarily arising through engagement with the messy real world continue to be raised. This chapter presents a qualitative analysis from a study of Year 9 students and illustrates how engagement with context offers opportunities to demonstrate and deepen genuine mathematical understanding of rate of change. Genuine collaboration and interthinking were found to facilitate the development of mathematical understanding clearly enabled by the real-world context.