This study examines the relationship between self-regulated learning (SRL), parent education, and the need to enroll in postsecondary remedial education courses, using first year college student data from the National Center for Education Statistics (NCES) Education Longitudinal Study of 2002 (ELS: 2002). This observational study was conducted using 6,149 sample elements for first-year college students, including 2,296 sample elements for students who enrolled in at least one remedial course during their first year in college. Observable covariates for high school grade point average (GPA) and standardized test scores were used in a cluster analysis to assign sample elements to either the treatment or control group. Propensity score matching was used to address selection bias and imbalances in the sample data, with stratification on the estimated propensity scores to create equal-sized strata composed of treatment and control group elements with equivalent pretreatment characteristics. Logistic regression was used to predict the odds that a first-year college student will need to enroll in at least one postsecondary remedial education course, based on observable covariates that represent self-regulatory behaviors, control of personal time, parental education, and demographic factors. After controlling for selection bias, self-regulatory behaviors were found to be highly correlated with enrollment in postsecondary remedial courses. The results indicate that self-regulatory behaviors, such as study habits and proactive control over use of personal time, and parent education are significant mediating factors between high school preparation and the need for postsecondary remediation.