Underprepared college students face transition issues that prevent full academic engagement. The written responses of 176 students in a learning-strategies course were used to develop a grounded model of overcoming barriers to academic engagement. Findings revealed contexts in which academic engagement involved high costs (i.e., effort, trade-off, or psychological burden). Students also demonstrated resilience in coping with academic costs. Implications include guiding principles student-affairs practitioners can apply to their work with underprepared college students.