Outdoor fieldwork has been a long-standing pedagogy in the higher education sector, across a range of disciplines. Based on a review of the literature, this paper explores the use of outdoor fieldwork in the 21st century university with particular reference to the way technology contributes to student learning. Research has indicated that fieldwork enhances student engagement, links theory and practice, and assists students with the development of professional expertise. Many of the challenges for outdoor fieldwork, such as budget cuts, risk management concerns, and workload demands on staff, have been exacerbated by massification pressures in universities, such as the growth in student numbers and a more diverse student cohort. The increased use of technology on outdoor field trips both solves and creates problems, and technology use in outdoor education has been described as a double-edged sword (Cuthbertson, Socha, & Potter, 2004). It can be difficult for teachers to judge whether the benefits to student-learning outcomes created by introducing technology outweigh any negative impacts. Koehler and Mishra's (2009) concept of technological pedagogical content knowledge suggests that teachers need to develop a very specific kind of knowledge to make informed decisions about the use of technology. The substitution, augmentation, modification, redefinition (SAMR) ladder (Puentedura, 2006) can contribute to this teacher knowledge by focusing on how the use of technology can transform student learning rather than just replace, or augment, existing teaching tools and strategies. Some examples of how technology is used at the different levels of the SAMR model in outdoor education are provided.