The college-going rates of rural students lag behind those of more urban students, a gap likely due, in part, to rural students' lower educational aspirations. These lower aspirations appear to be tied to the dilemma that higher education presents for many rural students: whether to remain in their rural home, working in traditional trades and industries that do not require a college degree, or to leave in pursuit of an education that is often the first step toward an adult life lived away. This study seeks to better understand this dilemma by examining the messages that rural, first-generation students receive about the value of higher education. Drawing upon interviews and observations, it shows that high school guidance counselors, college admissions officials, and the staff of community-based college aspirations organizations adopt a strikingly consistent message: they cite struggling rural economies in their argument for the necessity of a practical degree for all students, one that can be easily leveraged into a career. Despite noting broad parental support for this message, many participants also describe continued resistance from some rural families, a perception that may heighten the dilemma of rural college-going for students.