Recent legislation in Florida mandated that all school districts open at least one career academy by the 2008-2009 school-year, impacting career academy implementation dramatically. As the number of career academies in Florida increases, ensuring success requires attention to the complexities of implementation. Qualitative research conducted with a purposive sample of one school district was used to generate three case studies examined in this investigation. The Career Academy National Standards of Practice provide the basis for the study's conceptual framework. Student recruitment and scheduling, elements of Standard 2, presented obstacles to implementation. Academies were encouraged by early success in relationship-building among faculty and students and the real-world application of course content, elements of Standard 2 and Standard 7, respectively.