Endowments represent one of higher education's most vital financial resources, yet finance office often struggle with unclear spendable balances, manual allocation and reporting processes, and communication gaps across stakeholders. These challenges not only affect regulatory compliances and audit readiness, but can also erode the trust of donors, campus partners, and governing boards. This session offers practical, experience-based strategies for strengthening endowment oversight and improving the day-to-day accounting and reporting needed. Drawing on lessons learned over 24 years at the University of South Carolina Foundations, the session highlights how intentional fund structure and segmentation can transform endowment stewardship.