School leaders and policymakers seek various pathways to help minority, low-income, and other historically underrepresented populations matriculate to college after graduating high school. However, many students are not fully prepared academically or non-academically to transition to college, making it challenging to persist through completion and attain a degree. One innovative strategy to help students transition successfully is enrolling senior high school students in dual enrollment programs that expose them to college while still in high school. This qualitative research study explores teachers' and students' perceptions of factors that influence their successful transition to a college environment. The researchers interviewed ten high school teachers of senior high school students and three freshmen college students in the United States. The questions aimed to identify factors that high school teachers and freshmen might find helpful as senior high students matriculate to post-secondary education. The study produced three significant themes that affect students' transition from high school to post-secondary education: the improvement in college readiness, the development of non-cognitive skills, and the importance of student support in increasing college readiness and academic success. The study's implications and recommendations can help stakeholders engage in activities that aid in students' successful matriculation from high school to college. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]