A qualitative case study focused on understanding what steps are needed to prepare the cybersecurity workforces of 2026-2028 to work with and against emerging technologies such as Artificial Intelligence and Machine Learning. Conducted through a workshop held in two parts at a cybersecurity education conference, findings came both from a semi-structured interview with a panel of experts as well as small workgroups of professionals answering seven scenario-based questions. Data was thematically analyzed, with major findings emerging about the need to refocus cybersecurity STEM at the middle school level with problem-based learning, the disconnects between workforce operations and cybersecurity operators, the distrust of Non-Traditional Training Programs, and the need to build digital security generalists' curriculum and training. Recommendations are also made for possible next steps.