The study was conducted to investigate the relation of adolescent students' mathematics motivation and achievement to their appropriate help-seeking and inappropriate guessing behaviour while using instructional software. High school students (n = 90) completed brief assessments of mathematics motivation and then worked with software for geometry instruction. Students' actions with the software were machine-classified to identify instances of appropriate help-seeking and inappropriate guessing. Mathematics teachers provided information about students' achievement (high, average or at risk of failing math class). Results indicated that students with low math self-concept were most likely to engage in inappropriate guessing behaviour. Students with low math achievement were most likely to engage in appropriate help-seeking while working with the software.