This document summarizes two educational technology initiatives in South Africa that provided tablets and digital content to students. The first initiative provided tablets to two higher education institutions with about 14,000 students total. It aimed to transition to more flexible, technology-enhanced learning. Key challenges included limited bandwidth, converting existing content to digital formats, and managing communication across stakeholders. The second initiative provided tablets to schools in a rural district, emphasizing alignment with education policy and gaining support through teacher training. Both projects provide lessons for implementing 1:1 educational technology initiatives on a large scale in South Africa.