This chapter presents a multiple case study, where six veteran secondary education teachers participated in videotaped lessons, simulated recall, and semi-structured interviews. The findings highlight veteran teachers’ desired autonomy in selecting professional development, combined with opportunities to learn and practice with peers, as well as the unique generational challenges they face, while practicing in 1:1 settings. The findings suggest that: (a) veteran teachers will need customized, just-in-time professional development to help them acquire nuanced and critical understanding of how to best use their readily available technologies to enhance student content learning; and (b) intentional leveraging of veteran and novice teachers’ skills and talents in tandem, when professional learning communities are developed. Future theory building and description must include research-based strategies to best support secondary veteran teachers’ successful development of TPACK.