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Given that it costs around twice as much to educate special education students than general education students, it is important to ensure that special education services are effective at remediating academic and behavioral problems related to disability. Advocates argue that early intervention is the best approach (e.g. Wolery & Bailey, 2002), making it vital to ensure that at-risk children have access to these services as soon as possible. Yet, concern exists regarding the perceived stigma and (in)effectiveness of special education, particularly for non-white students (e.g., Burns & Ysseldyke, 2009; Collins et al., 2016; Shifrer, 2013; Sullivan & Proctor, 2016). In addition, developmental trajectories are often ignored in studies assessing the consequences of receiving special education services, even though students receiving earlier services likely have different educational needs and goals than students receiving later services (e.g., Marder, 2009). These differences necessitate caution when making claims about the effectiveness of special education without accounting for who receives services, and when. The current study assessed the development of academics, problem behaviors, and positive learning habits among special education students participating in the ECLS-K. The propensity to receive services in 1st grade versus 3rd grade was modeled by matching students who received services at least once during grades 1-8 on a host of Kindergarten covariates, ensuring that they began schooling with similar levels of achievement and behavior, came from similar backgrounds, attended similar schools, and experienced similar diagnoses, educational goals, services, and "amounts" of special education through 8th grade. Results indicate that students who received initial special education services in 1st grade made larger gains through both 3rd and 5th grade and scored 0.25 SD's higher on 3rd and 5th grade tests of reading than students who received services later in schooling. In contrast, students who received initial services in 3rd grade did not significantly differ from their peers on any academic outcomes. Moreover, there were no significant behavioral differences between students who received earlier (1st or 3rd grade) versus later services (5th or 8th grade). These results were robust to the method of propensity analysis used (e.g., stratification, kernel-matching) and imply that receiving special education earlier in schooling is associated with better reading performance and greater reading improvement over time than receiving services later in schooling. These results are also important for educational policymakers concerned with identifying at-risk students and providing the necessary special education services as early in schooling as possible.