Responding to mathematical problems is a core activity in classrooms. The problems that teachers select determine the mathematical content, processes and nature of mathematical inquiry occurring in classrooms and thereby contribute to the development of mathematical skills and dispositions. Selecting, designing or reformulating mathematical problems is a critical skill, then, for prospective and practising teachers. This study explores the influence of a mathematical letter writing initiative in developing the problem posing skills of 28 prospective primary teachers. We examine the characteristics of mathematical problems designed by prospective teachers, and their understandings of what constitutes a good mathematical problem, prior to and following completion of a 12-week letter writing initiative with 10–11-year-old children. Analysis of the data reveals the benefits of engaging in the initiative as evidenced in improvements in several problem characteristics. There was an increase in the number of multiple approach and multiple solution problems and in the level of cognitive demand of problems posed. The challenge of posing non-traditional problems, alongside the competing demands of building in opportunities for success, may have diminished participants’ ability to evaluate and attend to the cognitive demand of problems.