This document examines issues in schoolwide application of career academies. Part 1 reviews the three defining features of career academies: (1) a career academy is a small learning community in which a cluster of students share several classes each year that are taught by the same team of teachers over a period of 2-4 years; (3) each academy offers a rigorous and relevant college preparatory curriculum organized around a career theme; and (3) career academies immerse students in the adult world through partnerships with community groups (including employers, parents, and higher education) and activities connecting students to the world beyond high schools (including job shadowing, internships, service learning, and one-to-one mentoring). In Part 2, these three defining features of career academies are used to organize a discussion of some issues that arise when a high school moves to an all-academy structure. The following issues are among those discussed: deciding whether all academies should have career themes; specifying academy leaders' responsibility in relation to various administrators and counselors; and deciding how to achieve economies of scale in work-based and experiential learning. Part 3 describes three existing checklists and rubrics for monitoring implementation of individual career academies. (MN)