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Numerous studies indicated the potential of pupillometry in reflecting physiological responses. In the present paper, we applied a novel pupil estimation method to detect post-recording pupil response in an attempt to examine the relationship between pupil behaviors and learning behaviors, such as problem-solving ability and persistence. This paper is the first attempt at the application of online pupil study in measuring learning behaviors, aiming at extending the use of pupillometry to students' everyday learning context. Results from mixed-effect models suggested that pupil coefficient of variation and pupil dilation predict a higher success likelihood and persistence tendency, respectively. Findings align with previous studies using eye tracking equipment, indicating a partial reliability of utilizing online video as a source of pupil estimation.