This study uses a mixed methods approach to examine a new type of curriculum configuration that supports students’ transitions to college: career technical programs of study (POS). Interview and survey data were collected from a college and its feeder high schools in each of three well-established (“mature”) sites in geographically varied communities in the United States to investigate how POS are structured, what the key the “ingredients” are, and what students experience as they move through the POS. Interview findings suggest that the key elements of POS include dedicated staff to create secondary–postsecondary connections, active multistakeholder advisory committees, and flexibility and compromise in developing dual-credit options for students. Survey data show that high school students feel positively about their experiences in POS; however, career guidance is lacking. Student records indicate that even when POS were in place to support their transition, less than one-fifth of students remained in the same POS in college that they began in high school. Results are discussed in relation to the 2006 Perkins IV legislation.