As part of ongoing design-based research exploring financial literacy teaching and learning, ten tasks termed "financial dilemmas" were trialled by 14 teachers and more than 300 Year 5 and 6 students in 4 government primary schools in urban Darwin. Drawing on data related to two tasks--"Catching the bus" and "Buying bread"--this article explores insights into problem context and task design principles. The findings highlight that unfamiliar, novel, and imaginable problem contexts, while pedagogically demanding for teachers, are valued by students and have the potential to broaden their horizons.