While data forecast that America will face a shortage of skilled workers in technical and advanced manufacturing jobs within the next 10 years, enrollment in high school and college career and technical education pathways is down. Many of these jobs offer wages and benefits that equal or rival those of jobs requiring advanced degrees. If the demand for skilled workers exists, why is the supply of qualified applicants dwindling? High schools and community colleges offer coursework and hands-on training in these areas. Can these two systems work together to encourage students to enter career and technical education pathways? This disquisition addresses (1) the history of the declining enrollment in these programs, (2) the intersystems cooperation that must happen to matriculate students from high school to college Associate in Applied Science programs, and (3) one intervention that attempted to cross systemic barriers to connect high school staff and community college career and technical education programs.