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Universities are increasingly turning toward data-driven technologies like data dashboards to support advisors' work in student success, yet little empirical work has explored whether these tools help or hinder best practices in advising, which is in many ways a relationship-based enterprise. This mixed-methods study analyzed whether and why the release of a student success dashboard impacted proactive and/or developmental advising at a large public university. After quantitatively demonstrating no measurable changes in advising practice following the release of the dashboard, qualitative evidence from interviews with advisors was used to interpret and explain the disconnect between the tool and the advising community. This study places scholarly attention from a practitioner perspective on the largely structural challenges to integrating retention software into advisors' work in supporting their students' success, with implications for the successful implementation of data-driven student success tools more broadly.