Homeowners associations play an increasingly influential role in local stormwater management, yet their actions often determine whether a community stays compliant under Phase II NPDES MS4 permits. This presentation examines when HOAs, local businesses and school systems act as partners in stormwater stewardship and when they become barriers to compliance. Fayette County's experience surfaces recurring challenges: aging facilities, unclear ownership and inconsistent board turnover lead to lapses in maintenance and record-keeping. Proactive HOAs that budget adequately, maintain clear covenants and engage with the county in post-construction processes tend to achieve long-term compliance at lower cost. The session presents practical tools Fayette County uses to move these stakeholders toward cooperation, including standardized inspection forms, education campaigns, GIS-based asset tracking and direct board engagement. Case studies illustrate both successes and failures. The presentation also addresses MS4 legal authority, disputed maintenance responsibilities and strategies for gaining HOA buy-in.