This paper contributes to an ongoing discussion in the research community regarding the role of new technology in the lives of those experiencing homelessness. Ask Izzy is a mobile web app designed to help people who are homeless or at risk of becoming homeless ﬁnd the services they need. Since deployment in 2016, it is now attracting over 10,000 users each month. We explore the perceptions towards the design and use of Ask Izzy with a speciﬁc focus on emotional concerns. We interviewed 30 participants who were either homeless, ex-homeless, service providers or software developers of the web application. Seven themes emerged from the analysis that appeared to act as barriers or enablers to the uptake of the technology. We discuss how these themes are associated with aspects of technology design or an associated experience with a service provider. We also contrast the views of those who are homeless with service providers. We believe these themes will provoke discussion and be useful for others who are designing for those who are homeless.