For decades, researchers have struggled to describe a cohesive picture of underachievement among gifted students. This work has resulted in a wealth of empirical evidence that is, unfortunately, often characterized by mixed findings that seem contradictory. In this chapter, we propose a set of guiding assumptions that provide a new way of looking at gifted underachievement, both from a research and educational lens: (1) underachievement is inherently a developmental construct, (2) it is critical to look beyond the concept of “unmotivated,” and (3) a person-centered approach can help identify unknown patterns and pathways. Combining these assumptions, we highlight supporting evidence for (Snyder and Linnenbrink-Garcia, Educational Psychologist 48:209–228, 2013) Pathways to Underachievement Model and share both research and educational implications stemming from this model.