In this chapter, I reflect on five decades of experience and research about the underachievement of students with gifts and talents. This complex phenomenon is perplexing for educators and parents, as well as students themselves. My most intimate experience with it has been as a parent but my insights were most well-informed by a study that I conducted with my colleagues in the mid 1990s. This study is summarized in the chapter. My colleagues and I studied high school students identified as gifted and talented for almost four years, finding during those years, that half of these high aptitude students were underachieving by their senior year. A discussion of some of the causes, reasons, and remedies that can address this challenging problem is included as is a discussion about the ways that educators and parents can help to reverse underachievement and enable talents to be recognized and developed in these young people.