This study examines whether parental smoking and single parenting were related to adolescents’ school achievement and anti-smoking parental practices as well as how these factors predicted later smoking. The sample comprised 1163 Finnish students in Grades 7 through 9. Results show that at the beginning of the seventh grade, parental smoking and single parenting were related to adolescents’ lower levels of school achievement. Moreover, parental smoking had moderate association with lack of house smoking rules. At the beginning of the ninth grade, these associations were strengthened and lack of house smoking rules as well as loosened perceived parental punishment for smoking was related to both parental smoking and single parenting. The likelihood of ninth grade regular smoking was greater among adolescents whose parents smoked, who had no smoking rules in their homes and had substandard school achievement. These results suggest that smoking parents and single parents had similar anti-smoking regulations for their children at the baseline but once children became older smoking parents were not able to maintain these rules as successfully as non-smoking parents and families with two parents. Motivating parents to uphold these anti-smoking regulations offers a prospective intervention opportunity.