While character strengths have been found to predict educational outcomes beyond broad personality traits and cognitive ability, little is known about their differential contribution to success and positive learning experiences in different school settings. In this study, we use trait activation theory to investigate the relationships of students’ character strengths with achievement, flow experiences, and enjoyment in different learning situations (i.e., teacher-centered learning, individual tasks, and group work). In studying these relationships, we controlled for psychometric intelligence. Secondary school students (
N
= 255; 46.3% male; mean age = 14.5 years) completed a self-report measure of character strengths, the VIA-Youth (
Park and Peterson, 2006b
). Cognitive ability was assessed using a standardized intelligence test (PSB-R;
Horn et al., 2003
) at baseline. Three months later, students completed the Flow Short Scale (
Rheinberg et al., 2003
) adapted to the three learning situations and indicated their typical enjoyment of these situations. Both the students and their teachers (
N
= 18; 50% male; mean age = 44.8 years) provided ratings on school achievement in each of the three learning situations. Results indicate that, as expected, (a) certain character strengths (love of learning and perseverance) show consistent relationships with achievement and positive learning experiences (flow and enjoyment) above and beyond cognitive ability across all learning situations, whereas (b) other character strengths show differential trait-outcome relationships (e.g., the character strength of teamwork was predictive of achievement and positive learning experiences in group work). Taken together, these results suggest that different character strengths play a role in different school situations and that their contribution to explaining variance in educational outcomes is incremental to the contribution of cognitive ability.