Secondary school dropout rates are high in low-income countries, and information gaps about school characteristics may be an important contributing factor. If school choices are made with imperfect information, households may choose schools that are too expensive, not a good fit academically, or too costly to commute to, increasing the likelihood of the students dropping out. These information gaps may be further exacerbated when students and parents fail to communicate before making high stakes schooling decisions. I study the importance of these information and communication gaps in the transition from primary to secondary school using a field experiment with 3,000 Kenyan students and their parents. The intervention consisted of an informational meeting for 8th graders before they applied to secondary school, and randomly varied whether the parent participated in the meeting for a facilitated conversation with the student. I find that informational meetings with students led them to apply to more commutable schools at no cost to average test scores. Moreover, including the parents in these meetings improved parental knowledge about costs and led to better alignment of school preferences between the students and their parents. This ultimately led students to enroll in lower cost schools, which could generate meaningful savings.