This study examined how instructors and learners in residential outdoor education programs utilized mobile technologies and Web 2.0 applications. Twenty semistructured interviews were conducted with instructors, support staff, and administrators at a nonprofit institution that provides outdoor education programs. Sixty-five participants in those programs completed a questionnaire with open-ended questions. Results indicate that full-time instructors who were assigned an iPad utilized mobile technologies effectively and frequently. In contrast, seasonal instructors who had to check out iPads used them less frequently. Most instructors encouraged program participants to share digital media and use Web 2.0 tools. Program participants utilized a variety of mobile devices and applications during the programs. There was disagreement among instructors and staff, however, pertaining to the need for and the use of mobile technologies in outdoor education on public lands and in wilderness areas.