Objective: To explore the symptomatic features of homesickness in Australian adolescent males during their first year at boarding school, as well as its dimensionality, coping strategies, and the relationship with academic, resilience, emotional and mental health factors. Method: Drawing on a larger, longitudinal study (n = 174 students), survey responses were collected from 29 male participants aged 11–12 years at one non-government boarding school (K-12) located in Western Australia. Results: Exploratory statistical analysis found one-third did not experience homesickness, with almost one-third of participants experiencing a single episode of homesickness lasting for one week and one in five reporting recurrent episodes throughout the first year. Further, homesickness was not necessarily associated with specific negative emotions such as sadness or provoking problematic thoughts towards boarding school, cognitive impairment in class and somatisation. However, school-orientated homesickness was associated with a greater vulnerability to non-specific psychological distress, conduct problems, peer problems, and overall total difficulties. A range of productive coping strategies used by participants to ameliorate homesickness. Conclusion: Findings are discussed within the context of the existing literature and wider setting of adolescence and insight from a developmental science perspective. Potential implications for practice and future directions are presented, as they are the limitations of this study.