Secure accommodation provides extreme forms of control and support for a small minority of society's most vulnerable children. Within such environments it is unclear how children exhibit or develop self-regulation when external controls affect every aspect of day-to-day life. This study provides an insight into self-regulation by examining children's adherence to the rules associated with a practical form of philosophy, namely Community of Philosophical Inquiry (CoPI). Data was collected from a series of CoPI sessions which took place in secure accommodation and a thematic analysis was used to identify key themes emerging from participant's rule-adherence. The findings suggest that argumentative dialogue allows children to demonstrate self-regulation in relation to the CoPI rules, although it is often sporadic and variable between individuals. Whilst encouraging argumentation and dialogue can seem counterintuitive, it might promote more adaptive behaviours, which will give children in secure accommodation greater control over their lives.