While educational technologies are often considered a panacea for improving K-12 teaching and learning, they frequently produce unintended or problematic effects. Consequently, preservice teachers (PSTs) must be prepared to think critically, or "technoskeptically," when making decisions about the technologies they use in their future classrooms. The study described in this article implemented a series of learning activities during educational technology courses at two institutions, in which PSTs (n = 65) critically examined common classroom technologies, including Class Dojo and Teachers Pay Teachers. The researchers supported PSTs' inquiries using the "Technoskepticism Iceberg" as a conceptual scaffold, which directs PSTs to examine the technical, psychosocial, and political dimensions of technology. They analyzed PSTs' written appraisals of the technologies using qualitative content analysis, focusing on the types of arguments they made about the technologies and the extent to which their responses reflected critical thinking. They found that PSTs presented more deeply critical analyses of Class Dojo than of Teachers Pay Teachers, and results suggest that certain types of technologies are easier for PSTs to critique than others. Ways are discussed that teacher educators might further foster technoskeptical ways of thinking when working with PSTs.