This study examined the relationship between parental involvement and a proximal student academic outcome–active engagement, for a cohort of 160 students on their transition to secondary school and at three subsequent time periods. The student-reported measures were assessed using the Hoover-Dempsey and Sandler (2005) instrument. Results provide clear evidence of the ‘secondary slump’ phenomenon with a consistent decline in each of the four parental involvement subscales (parent modeling, parent instruction, parent encouragement, parent reinforcement) and with female students reported significantly higher levels of parental involvement than males. A similar pattern of decline emerged for students’ level of active engagement across the three years of the study; however, no gender differences were seen. In addition, the findings suggest a significant positive relationship between each of the four parental involvement constructs and active engagement. In discussing ways to address this ‘secondary slump’, discussions focused on a revision of the parental involvement instrument to include items which are more reflective of today’s increased use of the Internet and social media to facilitate interactions between parents and schools.