When a firm offers health benefits to workers, it exposes the firm to the risk of making payments when workers get sick. A firm can either pay health expenses out of its general assets, keeping the risk inside the firm, or it can purchase insurance, shifting the risk outside the firm. Using data on insurance decisions, we find that smaller firms, firms with more investment opportunities, and firms that face a convex tax schedule are more likely to hedge the risk of health benefit payments. We show how firms trade off the benefits that come from financing and investment characteristics with the costs of regulation when choosing insurance. We provide understanding of how firms’ policy and financial characteristics affect firm outcomes as the Affordable Care Act provisions impacting plan funding continue to evolve.