This study examines American high school students’ school-related information-seeking. Comparing advantaged and disadvantaged students’ practices, the research illuminates three phases of their information-seeking activities: 1) learning-opportunities for digital skill building, 2) information-retrieval tactics, and 3) information-evaluation strategies. The inquiry delineates several distinct categories of practice corresponding to each of these phases. In successful information-seeking, learning-opportunities enhance skill acquisition for effective information-retrieval that is followed by discerning information-evaluation. In unsuccessful information-seeking, inadequate learning-opportunities result in ineffective information-retrieval that is followed by disengaged information-nonevaluation. Significantly, gendered differences emerge in this final part of the sequence. Findings indicate that unskilled female information-searchers are more likely to adopt an overtrusting stance. By contrast, unskilled male information-searchers are more likely to adopt an undertrusting attitude towards online content. Both groups of unsuccessful information-searchers truncate this necessary evaluative stage and end the information-seeking process before it can bear fruit.