Supporting 21st century skill development calls for necessary changes in teaching practices to encourage contemporary learning outcomes. Research points toward technology integration as a catalyst for supporting shifting pedagogies necessary to enhance learning. As many Catholic educators and leaders are attempting to re-shape Catholic school learning for the 21st century, the Catholic school context provides a unique opportunity to understand technology integration and teaching practices. To address the need of understanding the development of teaching practices of Catholic educators in a digital age, this qualitative multiple-case study examines teaching practices of four middle-level Catholic school educators during a one-to-one technology initiative. Individual and cross-case analysis of the data revealed two considerable themes with regard to technology and 21st century thinking and enactment: shifting classroom dynamics influenced pedagogical approaches; and content played a central role in technology integration and instruction