The purpose of this study was to build a better understanding of the issues that students encounter during the summer that deter them from enrolling in the first semester of college in the fall. In Study 1, responses to a short survey were examined, and 4 critical factors were identified as deterring students: lack of college-bound identity, life circumstances and financial responsibilities, perceived lack of academic preparation, and opting for alternative career choices. In Study 2, transcription data were analyzed from texting dialogues between students and their college advisers. A thematic analysis revealed that several practical issues emerged with great frequency--most notably financial aid concerns. Social-emotional communication was also identified as a possible mechanism for developing the students' college-bound identity. These findings underscore the need to provide underrepresented students with not only information for completing college and financial aid applications but also with the opportunity for social support and emotional guidance during the summer leading up to college enrollment.