Teachers must be prepared to make informed choices about which technologies to adopt and how to implement those technologies in judicious ways. To support those choices, they need a critical "technoskeptical" perspective attentive to both the benefits and unintended effects of educational technologies. This study presents our effort to help elementary pre-service teachers (PSTs) develop a technoskeptical stance during an undergraduate educational technology course. A group of 45 elementary PSTs participated in ongoing learning activities designed to foster technoskeptical inquiries of educational technologies. Using a mixed methods approach, we analyzed PSTs' responses to those learning activities and their pre-and post-course philosophies of educational technology. We found that the inquiries did lead PSTs to adopt more technoskeptical views in their philosophies of educational technologies. Those changes were most substantial for the PSTs who demonstrated deeper critical analyses during those learning activities. However, changes in PSTs' thinking were not always what we intended or expected, pointing to a complex learning process. These nuanced findings imply a reevaluation of conventional perspectives on educational technologies and reinforce the urgency of cultivating technoskepticism in future educators.