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Online learning expanded considerably during the COVID-19 pandemic. How the shift online shaped students’ learning strategies has yet to be fully explored. Here, we examined how online vs. in-person learning influenced students’ expressed intellectual humility - willingness to admit confusion and mistakes. High school students (N = 1,380) completed open-ended surveys asking whether it was easier or more difficult to express intellectual humility online vs. in-person. More students found it harder to express intellectual humility online. The challenges of online school were contextual -- increased difficulty communicating, lower class participation, and technological problems -- and psychological -- anxiety, embarrassment, and difficulty focusing. Findings suggest ways that online learning environments might be improved to encourage students to express intellectual humility to maximize learning.