We provide evidence of persistent gender effects for students using advanced adaptive technology while learning mathematics. This technology improves each gender's learning and affective predispositions toward mathematics, but specific features in the software help either female or male students. Gender differences were seen in the students' style of use of the system, motivational goals, affective needs, and cognitive/affective benefits, as well as the impact of affective interventions involving pedagogical agents. We describe 4 studies, with hundreds of students in public schools over several years, which suggest that technology responses should probably be customized to each gender. This article shows differential results before, during, and after the use of adaptive tutoring software, indicating that digital tutoring systems can be an important supplement to mathematics classrooms but that male and female students should be addressed differently. Female students were more receptive than male students to seeking and accepting help provided by the tutoring system and to spending time seeing the hints; thus, they had a consistent general trend to benefit more from it, especially when affective learning companions were present. In addition, female students expressed positively valenced emotions most often and exhibited more productive behaviors when exposed to female characters; these affective pedagogical agents encouraged effort and perseverance. This was not the case for male students, who had more positive outcomes when no learning companion was present and their worst affective and cognitive outcomes when the female character was present.