New students face challenges when they make the transition from school to university. Existing digital technologies used during this transition can sometimes increase the stressors associated with change. In order to explore ways forward for technology design in this space, we developed a brochure of questionable concepts. The concepts were grounded in findings of our prior research, yet were also intended to act as provocations to promote discussion in workshops involving 32 first year university students. Our analysis of workshop discussions documents the diverse issues students face around social bonding, their home environment, and their academic performance. Our findings challenge assumptions made in prior work about the ease of transition to university. We demonstrate how questionable concepts can play an important role in prompting ‘safe’ conversations around stressful life events for adolescents.