Students' interest in mathematics is important for their learning of mathematics, and the ability to accurately judge students' motivational orientation is important for mathematics teachers. The aim of this study was to answer the following research questions: (1) Is there a difference in students' interest in solving problems with and without a connection to reality? (2) Is there a difference in pre-service teachers' judgments of students' interest in problems with and without a connection to reality? (3) Can pre-service teachers accurately judge students' interest in solving problems with and without a connection to reality? To answer these research questions, we administered a questionnaire in which we asked 100 ninth graders about their task-specific interest after they solved problems with and without a connection to reality. We additionally asked 163 pre-service teachers to judge fictitious ninth graders' interest in solving the same problems. Contrary to our expectations, students' interest in real-world problems was lower than their interest in problems without a connection to reality when task difficulty was controlled for. Further, our findings indicate an important discrepancy between students' interest and pre-service teachers' judgments of students' interest. Pre-service teachers overrated students' interest in solving real-world problems, and they underrated students' interest in solving intra-mathematical problems. Moreover, the accuracy of pre-service teachers' judgments of students' interest was low and ranged widely across pre-service teachers. Implications for teacher education and classroom practice are discussed.