School-going learners are vulnerable to behavioural un/wellness as they are situated in ever-changing contexts and cultures, potentially leading to adverse impact on their lives. Music, including songs, plays a crucial role in the lives of these children as they engage with, immerse in and even rely on songs for personal enjoyment, forging and sustaining relationships, shaping their identity and as a coping mechanism (Beckmann, 2013; Miranda, 2013; McFerran, 2012; Zoe et al., 2015). In music therapy settings, songwriting has been found to be an effective and meaningful means in helping children and teenagers to process and express their live/d experiences, thereby assuaging them from their struggles (Mayer, 1995; Dempsey, 2011; Johnson. 2016). Yet, songwriting tends to be implemented only in certain grades throughout the years of formal education in Singapore. This study aims to explore and advocate for the relevance and place of songwriting as a means of navigating behavioural un/wellness in school-aged children (7- to 12-year-olds) and teenagers (13- and 14-year-olds) in Singapore’s public-funded primary and secondary schools respectively. Unwell by Matchbox Twenty will be analysed and discussed to exemplify how songs can convey experiences and emotions effectively and affectively through the synthesis of sound and text in songwriting, therefore providing students dynamic opportunities for catharsis by conveying their live/d experiences, emotions and messages in songwriting and develop a healing relationship in and through music with themselves and those around them.