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Dual enrollment (DE), which allows high school students to take college courses and earn college credit through secondary-postsecondary partnerships, has gained popularity nationwide. However, what DE instruction looks like in the classroom—especially across diverse delivery contexts—is unclear. This comparative case study uses Mehta and Fine’s (2019) framework of deeper learning (mastery, identity, creativity) to examine DE instructor practice in high school and college contexts. Data come from two Texas community college districts and their high school partners. Findings indicate that deeper learning was rare in DE, regardless of where courses were taught. However, high school DE learning contexts compelled instructors to attend to student identity in ways that college contexts did not, with implications for deeper learning.