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This study is a multi-grant, longitudinal evaluation examining the relationships of student and family services provided by GEAR UP programs on FAFSA completion, secondary school graduation, and postsecondary enrollment. Logistic regression was employed to examine the impact of individual student and family services on the three outcomes. Results of the analysis were mixed, but the aggregate GEAR UP service variable was statistically significantly and positively related to FAFSA completion and postsecondary enrollment. These findings are significant because this study is the first of its kind—a grassroots, grantee-led collaborative evaluation of a federal grant program. Second, this study provides best practices for large-scale evaluation and information on which college and career services may of more importance to particular student outcomes.