Abstract Design Thinking techniques have been widely used in software requirements elicitation to understand the necessities of stakeholders and end‐users. However, there is a lack of evidence of their effectiveness when applied to guide the development process of a system targeting vulnerable populations. What are the implications of using Design Thinking techniques to elicit requirements in a community of former inmates—and what would be the benefits of and challenges in this deployment? In this paper, we report our experience of using Design Thinking for requirements elicitation of a mobile application customized for the former inmates of the Brazilian prison system and their families. We applied techniques such as Brainstorming, Stakeholder Mapping, Personas Creation, Rapid Ethnography, and Interviews to obtain relevant data and create several prototypes. These techniques contribute to the development of an uncommon application that aims to help the reintegration process of former inmates into society. Our results validate the initial hypothesis that such techniques, when applied to a sensitive context, assist product development that meets the end‐users' needs by creating a higher quality product. The main limitation of the research was the lack of access to low‐literacy end‐users and/or former inmates without previous experience using mobile devices.