This paper will report findings from two case study schools in England regarding the way in which pastoral care, pupil welfare, and pupils’ personal development are approached within the statutory framework of Personal, Social, and Health Education (PSHE) and Social, Moral, Spiritual, and Cultural (SMSC) Education. The main aims of the research were a) to find out how theoretical aspects of PSHE and SMSC play out in the actual school context and b) to what extent issues of mental health and therapeutic aspects play a role in the schools visited. Despite the differences between the two schools in terms of catchment area, pupil body, size, etc., there are similarities in the way they approach pastoral care and pupil welfare, with both schools taking issues relating to pupils’ personal development and welfare very seriously and seeking to equip pupils with all the skills they need for life, not just academic achievement—hence references to ‘essential life skills’ and ‘Learning for Life’. The paper will report the schools’ strategies of promoting and imparting such skills to pupils within their respective community contexts as well as the rationale and motives for putting such strategies in place.