The purpose of this quantitative secondary data analysis was to examine the effect of family, school, and community context on high schools whose students participate in financial aid preparation services. Data from the High School Longitudinal Study of 2009 were analyzed to answer the two research questions using Perna's conceptual model of college enrollment behaviors that explores how students gain and utilize information about financial aid and college prices. Descriptive statistics were used to determine the extent of high school participation in financial aid services. The results indicated a varying degree of these interventions being offered at high schools ranging from 22% to 52%. Schools sending students reminders of FAFSA deadlines (52%) and disseminating flyers/pamphlets on financial aid (50%) were the only two interventions that had a slight majority of schools participating. Multiple regression was used to determine if a relationship existed between the outcome variable (participation in financial aid preparation services) and several family context and school context predictor variables for eight financial aid interventions. Results revealed school context variables as the best predictors of the outcome variable. Counselor caseload and school control were the most effective in predicting high school participation in the eight financial aid preparation services, though these greatly differed according to the type of intervention. Findings provide potential implications for research and practice, including highlighting ways in which K-12 and higher education can coordinate.