Several recent studies have successfully identified college student typologies based on individuals' behaviors. One limitation of past studies has been their reliance on one-time cross-sectional assessments. As a result, we are left to ponder the stability of students' behavioral types as their academic years move forward. This study used longitudinal student data from high school to college, to investigate the stability of a behavior-based student typology. Guided by findings in behavioral consistency from personality psychology, this study explored the associations of higher education institution's structure, and supportive elements of the environment and the transition of students' behavior-based types. The results showed that, in high school and higher education settings, students' behaviors in a variety of activities classified students into four types. In the higher education setting, about half of the students were of the same behavioral type while the remaining students engaged in changes as compared with their behavior-based types in high school. Students' background characteristics and institutional environment demonstrated an association related to these shifts.