Ensuring that young Black men are afforded equal educational opportunities, access, and outcomes in education remains the most pressing challenge of modern schooling. Critical to overcoming this challenge is a focus on engineering pathways to design for school-based initiatives which draw more comprehensively from research and the prevailing negative public discourse. Utilizing a critical engineering lens, the authors examine how existing pathways to design limit the possibilities for young Black men in schools. Three propositions are offered as essential for design: (a) rejection of deficit language in public discourse; (b) establishment of critical orientations toward school and social barriers; and (c) acknowledgement of a culturally centered, multidimensional notion of masculinity. These propositions are discussed and a reengineered model for creating these experiences is proposed which may assist educators in developing relevant, successful school-based initiatives involving young Black men. (Contains 2 figures.)