As part of ongoing design-based research exploring financial literacy teaching and learning, 10 tasks termed "financial dilemmas" were trialled by 14 teachers and more than 300 year 5 and 6 students in four government primary schools in urban Darwin. Drawing on data related to three tasks--"Catching the bus," "Laser Tag" and "Buying bread"--this article explores insights into problem context and task design principles. The findings highlight that fit to circumstance, challenge yet accessibility and pedagogical architecture are important task design principles. Further, tasks involving unfamiliar, novel and imaginable problem contexts, while pedagogically demanding for teachers, can be considered useful by students and have the potential to broaden their horizons.