Agricultural entrepreneurs in the Philippines continue to face persistent risks that undermine productivity and resilience, yet most rely on traditional coping practices that are insufficient against large‑scale disturbances. In Davao Oriental, where diverse enterprises such as crop farming, livestock, agro‑processing, and aquaculture operate, there remains a gap in understanding how agripreneurs manage risks across different sectors and what strategies sustain their operations. This study aimed to explore and analyze the risk management operations of agricultural entrepreneurs through a qualitative multiple‑case design. Five cases were purposively selected, and data were gathered through in‑depth interviews, triangulated with observations and stakeholder validation. Thematic and cross‑case analyses revealed four major themes of risk: human resource, financial and market, legal and institutional, and operational. Common challenges included shortages of skilled labor, unstable commodity prices, costly regulatory requirements, and vulnerability to severe weather, while sector‑specific differences emerged, such as livestock farmers’ emphasis on reliable workers, aquaculture’s exposure to predatory animals and water fluctuations, and agro‑processors’ struggles with logistics and biosafety. Despite these vulnerabilities, entrepreneurs demonstrated resilience through diversification, cooperative networks, climate‑smart practices, and resource sharing. The study concludes that risk management among agricultural entrepreneurs in Davao Oriental is not only about mitigating losses but also about sustaining livelihoods and building resilience, offering contextual insights that can inform policy, extension services, and future research.