Documentation is part of a critical foundation of skills in the undergraduate medical education curriculum. New compliance rules from the Centers for Medicare and Medicaid Services will impact student documentation practices. Common barriers to student documentation include limited access to the electronic medical record, variable clerkship documentation expectations, variable advice regarding utilizing the electronic medical record, and limited time for feedback delivery. Potential solutions to these barriers are suggested to foster documentation skill development. Recommendations are also given to mitigate compliance and legal risk.