Baltimore City Public Schools (City Schools) has made great strides in its effort to lower the number of high school dropouts and to encourage prior dropouts to return and graduate by providing a broad set of options for students with a diverse set of needs and academic histories. At the same time, City Schools has initiated an effort to foster a college and career-ready culture in its schools. Across different high schools and even within the same school, students hold vastly different aspirations for adulthood and expectations about careers. The findings in this report reflect this tension, as the authors note that as high school graduation numbers have gone up, trends in college enrollment have declined somewhat over recent years, and more graduates are choosing 2-year instead of 4-year institutions. The hope is that the findings of this study will help guide City Schools and local institutions of higher education toward making the necessary steps to improve the educational opportunities of City Schools students. The following appendices are included: (1) Data Sources and Collection Methods; (2) Data Processing and Methods of Analysis; (3) Graduation (Leaver Rate) and Fall College Enrollment for the Baltimore City Schools Graduating Classes of 2008 through 2012; (4) Baltimore City Schools Classification by Year; and (5) Most Frequently Fall-Enrolled Institutions of Higher Education Attended by City Schools Students from the Class of 2012, by Barron's Competitiveness Ratings.