Coach retention is a crucial issue for sport delivery systems in most countries. Studies directed towards understanding why volunteers choose to remain involved have tended to focus on personal motivations and dispositions with generally less attention given to the organisational setting in which volunteers work. Using data from focus groups and archival material, the aim of this research was to examine the extent to which interactions between volunteer coaches, the immediate club setting, and the broader AFL context influenced the decision of coaches to either leave their club or remain involved in coaching. The findings reveal that the decision by volunteer junior football coaches to leave is not driven by the same underlying factors as the decision to stay. Enjoyment, success (manifested through either team wins and/or player/team improvement), and the nature and level of support from parents, the club, and the league, were identified as the key factors contributing to the decision to stay involved as a volunteer coach.