The study sought to examine young people’s life satisfaction in the context of the family environment, using data from the 2006 HBSC: WHO-collaborative Study in Scotland (N = 5,126). Multilevel linear regression analyses were carried out for 11-, 13- and 15-year old boys and girls, with outcome measure ridit-transformed life satisfaction. The study found there to be a relationship between family structure and life satisfaction for boys and girls aged 13 and 15 years. Family affluence mediated this relationship, however the extent of this mediation depended both on age and gender. For both boys and girls at all ages, life satisfaction was more strongly associated with parent–child communication than with family structure or family affluence. After adjustment for risk/health behaviours and attitudes towards peers and school, family structure remained significant for boys aged 13 years only. Whereas difficult parent–child communication acted as a risk factor of low life satisfaction for boys and girls, easy communication acted as protective factor among girls only.