The present article focuses upon particular findings from a mixed-methods study that examined the leadership strategies Antiguan school principals employed to incorporate technology into the teaching and learning process. The aim was to provide greater insight into these strategies, as well as, to identify some of the successes and challenges associated with the incorporation of ICT by these secondary school principals. This study was anchored by the International Standards for Technology in Education (ISTE) model, an established technology leadership theoretical framework. Qualitative data were gathered from school principals and teachers through the use of semistructured interviews (N=27). Furthermore, the qualitative data were manually coded and subjected to thematic content analysis. Regarding ICT integration, findings on leadership strategies highlighted a number of developing themes related to successes and challenges, in areas such as communication with key stakeholders, ICT resource allocation, attitude of educators towards ICT integration, and administrative activities.