Supporting prospective elementary teachers (PTs) to develop mathematics problems with contexts that reflect their students’ lives is a challenge that remains to be explored. We began this work by conducting collaborative action research to explore PTs’ development of mathematics problems that were relevant and authentic to PTs’ own lives. We engaged in iterative cycles of action research by asking PTs to write mathematics stories, followed by our review and discussion of the themes we saw and sharing selected examples with PTs during class discussions. Findings after three cycles of data collection suggest that PTs’ mathematics contexts became more story-like and personally authentic, and the authors (mathematics teacher educators) developed a clearer understanding of their goals for supporting PTs’ development.