Many young people experience difficulty finding and keeping their first independent home, which can lead to homelessness or risk of homelessness. To help address this challenge, a young people’s service in Scotland (Calman Trust) is developing a digital tool called HasAnswers. This paper provides a brief description of HasAnswers, the results of iterative testing with 69 young people (40 male, 29 female) using paper and digital prototypes, and feedback from other services with a responsibility for supporting young people to achieve an independent adulthood, as a potential customer base for the future scaling up of HasAnswers to new geographical locations and organizations. While preliminary, the results/feedback has been consistently to confirm the potential usefulness and acceptability of HasAnswers. Next steps include applying the results of the latest user testing followed by pilot testing. The research contributes to the body of work within HCI on design for homelessness by providing a new digital tool with a greater emphasis on prevention and early intervention, informed by an iterative user-centred design process.