The acquisition and mastery of emotion regulation is one of the most important developmental tasks of adolescence. Difficulties in regulating emotions are one of the most robust risk factors for the development of difficulties and psychopathology. This study investigates whether a mindful parenting style is associated with adolescent’s difficulties in emotion regulation and whether adolescents’ self-compassion and psychological inflexibility mediate this association. This study also explores gender and age differences in study variables and the moderating role of adolescents’ gender and stage of adolescence in the mediation model. A total of 375 mother-adolescent dyads participated in the study. The adolescents had a mean age of 14.19 years (SD = 1.67; range = 12–19 years) and 59.5% were girls. The mindful parenting dimensions of compassion for the child and nonjudgmental acceptance of parental functioning were indirectly associated with difficulties in emotion regulation through self-compassion, whereas the mindful parenting dimension of listening with full attention was indirectly associated with difficulties in emotion regulation through psychological inflexibility. Some associations were only significant for girls. These findings suggest that mindful parenting is a possible vehicle to foster adaptive emotion regulation in adolescents by facilitating their self-compassion and psychological flexibility.