Middle school is a critical time in students' learning of mathematics, something a Learning Management System (LMS) is designed to help parents support. What remains unknown is how parents use an LMS to monitor their children's progress in mathematics. This qualitative case study explored how parents from one midAtlantic middle school with 543 students used an LMS, EdLine, to support their children's autonomous achievement in mathematics. Expectancy-value theory and social cognitive theory made up the conceptual framework used to evaluate study findings. A criterion-based process was used to select nine middle school parents from grades 6, 7, and 8 as participants. Data sources included structured interviews and follow-up questions, EdLine spreadsheets, and parent reflective journals. Data were analyzed through a priori codes based on the literature review. Themes that emerged from the analysis included reoccurring learner autonomy and parents benefiting from their ability to use EdLine to monitor grades, check progress, and provide strategies to support mathematical achievement. Parents indicated they could encourage their children, teach them, and expect them to use EdLine to monitor and manage their grades and achievement in mathematics. This research contributes to positive social change by explaining how administrators can help middle school parents use an LMS to become engaged with their children's mathematics studies and set expectations for their mathematics task completion and achievement.