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This paper describes the development, field testing, and adaptation of the middle and high school dropout prevention intervention Check & Connect for the community college setting. The Making the Connection model engages community college students with college and learning using four components: (1) A small group made up of community college students who want/need extra support; (2) A mentor/small group leader who keeps the focus on achieving the student’s academic and career goals (transfer, 2-year certificate, etc.). The mentor actively facilitates the group and is available for individual mentoring; (3) Systematic monitoring by the student with feedback from the small group and mentor; and (4) Intentional and timely, individualized “interventions” designed to help the student stay on goal.