Context personalization—the incorporation of students’ out-of-school interests into learning tasks—has recently been shown to positively affect students’ situational interest and their performance and learning in mathematics. However, few studies have shown effects on both interest and achievement, drawing into question whether context personalization interventions can achieve both ends. The effects of personalization are theorized to result from activation of students’ prior knowledge of personal interests and generation of situational interest in math tasks, though theorists have begun to question whether situational interest serves as a mechanism by which learning outcomes are achieved. This experimental study examines whether personalizing 4 units of algebra problems that high school students (N = 150) solve in an intelligent tutoring system could improve their performance in units (i.e., accuracy and learning efficiency) and on classroom exams, whether adolescents who solved personalized problems would report greater situational interest in units (and later, individual interest in math) than peers who solved standard problems, and whether paths through situational interest would contribute to effects of personalization on outcomes. High school students in the personalization condition reported greater triggered situational interest in experimental units, and triggered interest predicted in-tutor outcomes (accuracy, learning efficiency). A total effect of personalization was also observed on classroom exam performance and individual interest in mathematics. Implications for theories of interest and context personalization are discussed, as are implications for math instruction and design of personalized learning environments.