In 2016, State University (a pseudonym) implemented a proactive advising approach known as Monitoring Advising Analytics to Promote Success (MAAPS). The initiative was designed to improve academic achievement and retention measures for first-generation students and students from limited-income backgrounds. Using a qualitative methodological design, the purpose of this study was to learn about students' experiences with MAAPS advisors and their overall perceptions of the program. Findings confirm prior research that suggests some students may benefit from advisors' proactive communications and holistic approach. However, the design and implementation of MAAPS discouraged many from participating in the initiative, highlighting several implications for improved future practice.