Dual enrollment has continued to increase in popularity as an effective means of introducing students to college and encouraging postsecondary enrollment. Students are introduced to the academic rigors and expectations of a college environment, while developing college readiness to transition to postsecondary institutions beyond high school graduation. Increasing student participation in dual enrollment programs is often due to the appeal of financial and time savings for the student and their families, however this can come at a cost. Using a qualitative study design, I sought to explore the engagement and relationships among the high school guidance counselor, college academic advisors and the dual enrollment participants. I was interested in how the engagement between the three parties influenced the transition experience at different stages of transition from being a high school student participating in a dual enrollment program to then becoming a post-secondary student. This study was guided by three research questions: (a) What were the experiences of being a DE student?, (b) What were the experiences of dual enrollment students as they transitioned to post-secondary institutions?, and (c) In what ways did communication with high school counselors and college advisors impact DE students' transition to college? With the use of my conceptual framework and Nancy Schlossberg's Transition Theory of "moving in", "moving through", and "moving on", I was able to identify the following themes through pre-study questionnaires and individual student interviews: (a) preparing students for dual enrollment programs, (b) preparing dual enrollment students for a higher education experience, and (c) preparing dual enrollment students for higher education degree programs. Each individual theme also had their own identified subthemes as well. Results indicated conflicted communication and differences within information provided at different stages of the students' transition, based on their dual enrollment program and the counselors and advisors within their schools. Implications from this study are the following: communication from dual enrollment administration and practitioners influences the transition experience of DE students into their postsecondary institutions. Specifically, attention should be focused on, (a) State of FL policy, (b) counselor and advising requirements, and (c) transferrable credits, as of these all have an influence on the transition experience for dual enrollment students. [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.]