Advances in learning approaches can enhance deeper levels of mathematical thinking and engagement through the use of new digital environments and technologies. The growing utilisation of portable digital devices in schools has meant there are enhanced tools to support mathematical learning and understandings. This article focused on those who work together to provide learning approaches in mathematics for 11- to 13-year-old students in New Zealand primary schools. The research study involved six schools, chosen to reflect a variety of school types and populations. We interviewed six principals and eight teachers about aspects of eLearning in their school mathematics programmes. The study found that the cost of some programmes and the lack of Internet connections and lack of computers in poorer homes did not allow for a level digital playing field for all children. Teachers considered eLearning as an opportunity to practice skills in a high interest and varietal way. However, in some cases, the teachers had little confidence to use information and communications technology (ICT) effectively. Only one school provided ongoing professional development on ICT use for mathematics learning. Even though many of the classrooms were well resourced, the teachers did not appear to have knowledge of learning approaches which encourage higher-order thinking skills to raise mathematics achievement.