A growing body of research suggests that, compared to normative adolescence, adoptive adolescence could be considered a specific risk condition characterized by more psychiatric problems, attachment insecurity, and emotional regulation difficulties as consequences of negative experiences in preadoption relationships. The current study explores (a) a moderation model of adoption status on the association between attachment representations (secure, dismissing, preoccupied, and disorganized) and behavioural problems and (b) a moderation model of adoption status on the association between emotion regulation processes (cognitive reappraisal and expressive suppression) and behavioural problems. Both the moderation models were controlled for verbal skills. Forty-six adopted adolescents and a control group of 34 nonadopted peers (12–16 years old) living with both their biological parents were assessed using the Friends and Family Interview, the Emotion Regulation Questionnaire for Children and Adolescents, the Child Behaviour Check List 6–18, and the verbal subtests of the Wechsler Intelligence Scale for Children, the latter as control measure. Results showed that adoption status (but not attachment) positively predicted externalizing and total behaviour problems, whereas attachment disorganization (but not adoption status) positively predicted internalizing problems in both group. Moreover, low cognitive reappraisal had a negative impact on externalizing problems only for adopted adolescents, but not for nonadopted youths. The clinical implications of these findings are discussed in order to enhance effective intervention with adopted adolescents and their parents.