The effectiveness of the Check and Connect dropout prevention program was examined, over the course of 2 ½ years, with 54 middle school students from diverse backgrounds experiencing one or more conditions of risk for dropout. Participants were randomly assigned to receive the Check and Connect intervention or business as usual (i.e., control) in sixth grade. Students in the treatment group had significantly better eighth grade attendance than the control. There were no significant differences between the two groups in eighth grade cumulative grade point average or office disciplinary referrals. An in‐depth analysis of the quality and quantity of the intervention delivered to the students in the treatment group identified conditions that were associated with higher treatment integrity and better student outcomes.