Today, most everyday music listening is an accompaniment to other activities; it is far less common that listening is someone’s primary activity, receiving most of their attention. In this article, we present a case study, Listen Up, run by Indigo Project, a mental health organization in Sydney, Australia, in which we explored relationships between participants’ responses to the experience and their demographics and styles of music engagement. A sample of 187 Australian residents (aged 20–64 years) who attended Listen Up completed a survey measuring music engagement; emotional responses to the experience; perceived outcomes of the session; pre- and post-measures of stress, mood, and anxiety; and free-text responses to questions concerning their experiences of listening mindfully and any thoughts or feelings that arose during the session. Participants experienced an increased mood and decreased levels of stress and arousal after taking part in Listen Up. Their focused-listening experiences were not simply characterized by enjoying the music; rather, the emotions evoked were varied and complex. We characterized their emotional responses as negative, positive, evocative and expressive, and sad; in addition, participants characterized their own experiences as a cathartic journey resolving into a positive, peaceful, and calm state. Reported outcomes of participating in Listen Up included experiences described as being emotionally challenging, therapeutic, and physically uncomfortable. An affective music engagement style was positively associated with evocative and expressive and sad emotional experiences, and therapeutic outcomes. As a focused-listening experience, Listen Up provides participants with the opportunity not only to attend to music but also to reflect on and process their personal thoughts and feelings. This research provides evidence for the emotional and mental health benefits of focused music listening, such that, focused listening reflects opportunities for strong experiences with music in today’s listening landscape.