Adopting speech as their mode of interaction, speech-enabled conversational agent (CA) systems hold the potential to enable more natural and engaging self-report experiences than traditional media (e.g., pen and paper, web, or smartphone systems). Our recent research concerns the potential design and use of CAs to support mental health and wellbeing. In this article, we present findings from a study during which 22 individuals with affective disorders (e.g., depression, bipolar disorder) used either a speech-enabled CA or web app to self-report their emotional wellbeing. Analysis of users’ experiences and engagement with the system for daily self-report suggests that despite many technical limitations, users rated self-reporting via CA as a significantly novel and attractive experience yielding similar rates of engagement to a traditional web-based method