The paper focuses upon the development of self-regulation as it pertains to pupils experiencing social and emotional behavioural difficulties (SEBD) within the context of a case study evaluating an intervention, designed and implemented by the author, to support such pupils within a Scottish secondary school situated in an area of multiple deprivation. The paper examines the extent to which pupils participating within the intervention developed the capacity to regulate their behaviour with good judgement in a range of contexts, identifying variables which fostered or impeded progress. The study is principally qualitative but draws also from quantitative data. It focuses upon four cohorts of support group pupils (N = 69), inclusive of six case studies. The findings indicate that the intervention had impacted positively upon the capacity of the young people to self-regulate their behaviour, if to varying extents, and that pupil outcomes were highly context related. (Contains 3 notes, 5 tables, and 2 figures.)