Although much national effort has been made to align the K-12 and higher education systems, the educational pipeline is still leaky at every stage. Furthermore, one of the on-going issues in the educational system is the lack of readiness of high school graduates for post-secondary education, especially for low income and minority students. As a result, there is a staggering number of students who enter college and are placed into non-credit-bearing, remedial courses. One of the goals set by the Department of Education (DOE) is to decrease the number of Hawai'i high school graduates enrolled in remedial education. This qualitative study adds to the body of literature by providing an increased understanding of "low-router" students' choice to enroll in remedial/developmental math versus college math at a community college by examining their perceptions and attitudes. Consequently, five distinctive themes emerged from this study. They were: (1) student characteristics, (2) path, (3) factors that explain "low-router" students' perceptions and attitudes, (4) "low-router" students' understanding of their situation and (5) constituents that supported or hindered "low-router" students' choice of math placement. As a result, this study provided several recommendations for high school and college administrators to improve current practices in order to support and encourage students to prepare for college, transition into college and decrease the number of high school graduates enrolled in remedial education. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]