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Abstract: Electronic portfolios (eportfolios) are increasingly used to assess student development. The degree to which faculty in North American medical schools are confident in their ability to evaluate such materials and their perceptions of the utility of eportfolios are unclear. Thirteen medical educators developed skills necessary to critically assess students’ reflective essays. Qualitative methods were used to explore faculty experiences with a socio‐cultural eportfolio. Despite self‐perceptions of being novice users, faculty were willing to engage with the eportfolio and assume an unfamiliar role in guiding medical students’ personal reflections. Additionally, we uncovered unique faculty expectations regarding the quality of students’ essays and their thoughts about the utility of an eportfolio as an assessment tool. Our findings indicate that given adequate time and training, faculty will use an eportfolio. They believe it is an effective method for both longitudinal assessment of student learning and achieving curricular objectives. Our findings also illustrate the numerous unintended ethical challenges faculty encounter as they engage in student assessment.