Parents whose self-esteem is contingent on their children’s achievements tend to exert more control over their children by displaying decreased affection and regard after failure in school (parental academic conditional negative regard). The current study examined parental anger and dysregulated anger expression as possible mechanisms in the respective association. In total, 221 mothers reported their child-invested contingent self-esteem, habitual dysregulated anger expression, anticipated anger after child failure, and their explicit use of conditional negative regard; their 12- to 14-year-old adolescent children reported perceived conditional negative regard. The moderated mediation analysis revealed that anger after child failure partially mediated the effect of child-invested contingent self-esteem on maternal explicit use of conditional negative regard, which, in turn, predicted adolescents’ perception of conditional negative regard. The effect of anger was moderated by dysregulated anger expression, and anger was only positively related to conditional negative regard when expressed as medium- to highly-dysregulated. The results support our hypotheses and provide an explanation for parental application of conditional negative regard apart from socialization goals or a lack of knowledge about its suboptimal nature. Furthermore, our results underscore the importance of parents’ self-esteem concerns and strategies for anger regulation. We discuss the practical implications of an anger-driven, reactive type of conditional regard.