This qualitative study investigated second semester undergraduate college students' perceptions of their levels of college readiness instilled and developed in them as graduates of a New York City High School. This study sought to determine the level of alignment of the criteria and definitions of college readiness between the New York City Department of Education, the New York State Education Department, and the City University of New York. According to data revealed by the College Board in 2015, the number of students graduating high school who are considered college ready is 28 percent. This phenomenon has been verified by the College Board, ACT, the New York City Department of Education and the New York State Education Department. The research found that there was an alignment regarding college readiness criteria among the New York City Department of Education, the New York State Education Department and the City University of New York (CUNY). On the other hand, the current definitions of college readiness determined by educational organizations at the state and local levels were analyzed and it was found that they do not align with actual experiences of college freshman students. The interviews of thirteen undergraduate college freshman participants from a predominately Title 1 high school indicated that the students did not feel that they graduated with the skills, attitudes and attributes to be successful in 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.]