The PreK-12 and higher education systems operate as separate and distinct entities (Kirst & Venezia, 2004). States organize them as separate units and the administrators in the systems are formally trained separately and operate separately with few exceptions. While studies have been conducted from the PreK-12 and higher education perspectives in terms of how to bridge this gap for students, little has been done to gather the ideas of those directly involved in bridge programs such as the TRIO programs that exist in the reauthorization of the Higher Education Act. This study searched for insights into systemic issues due to the two separate systems from the perspective of those "on the front line" of bridge programs rather than from individuals in positions of authority. Bridge programs, as understood here, are those programs specifically intended to help students transition from the PreK-12 environment to the higher education environment. Using a convenience sample, the study has focused on those working within a TRIO program. Participants selected for this mixed methods study include "front-line" individuals who are employed to work directly with students to facilitate the transition. These include people who have titles such as advisors or counselors, who are affiliated with TRIO, and who identify as working directly with students more than 50% of their time. The over-arching intent was to examine what insights these individuals, working directly with students, might have regarding potential barriers and facilitative processes.