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Numerous researchers have examined school and student variables that can prevent school failure, dropping out, and the development of delinquent behaviors. Such research suggests that students who establish a strong connection to school early in their academic career have higher academic achievement, better attendance, and more school participation (J. D. Finn, 1989, 1993; Finn & Rock, 1997; Sirin & Rogers-Sirin, 2005). However, there is little research that evaluates mechanisms that could be used to intervene when older students are on course for failure or delinquency. The current study, therefore, attempts to expand on the understanding of precipitating factors for school connection by investigating a possible link between school connection, extracurricular activity participation (EAP), and the relationships with teachers, parents, and peers promoted through activity participation. Latent variable structural equation modeling was used to investigate whether relationships with teachers, parents, and peers mediate the effects of EAP on school connection across time. Data from the base year (8th grade), first follow-up (10th grade), and second follow-up (12th grade) waves of the National Educational Longitudinal Study: 1988-2000 (NELS:88) were used. Three latent variable panel models were created and analyzed; one each for Relationships with Teachers, Relationships with Parents, and Relationships with Peers as the mediating variables. Results supported previous literature in that models reflecting a reciprocal relationship between EAP and school connection were found to have the best fit. Additionally, latent variable structural equation models were constructed to simultaneously compare the influence of EAP on the three types of relationships (i.e., with teachers, parents, and peers) and their subsequent influence on school connection. Finally, a latent variable structural equation model was constructed to explore possible differences in the type of activity in which a student participates on their relationships with others and school connection. / text