In this article, we share what we learned about undergraduates’ struggles in writing quality summaries, comparison texts, and argumentative essays that were components of a unique course, Learning How to Learn. This course was designed to address core psychological issues that impede optimal learning for students from all majors, many of whom are preparing to attend professional or graduate school. Although never intended to be a course devoted to academic writing, the struggles we uncovered made it apparent that without addressing these students’ writing difficulties, especially with argumentation, optimal learning was not achievable. For each form of writing central to the course (i.e., summaries, comparisons, and argumentation), we not only describe the challenges we have documented over the past six years, but also the instructional responses we instituted to counter those challenges. We conclude by sharing insights we have garnered from this experience that may serve others who are confronting similar issues in their students’ writing abilities.