This dissertation continues the tradition of identifying the unintended consequences of the US health insurance system. Its main contribution is to estimate the size of the distortions caused by the employer-based system and regulations intended to fix it, while using methods that are more novel and appropriate than those of previous work. Chapter 1 examines the effect of state-level health insurance mandates, which are regulations intended to expand access to health insurance. It finds that these regulations have the unintended consequence of increasing insurance premiums, and that these regulations have been responsible for 9-23% of premium increases since 1996. The main contribution of the chapter is that its results are more general than previous work, since it considers many more years of data, and it studies the employer-based plans that cover most Americans rather than the much less common individual plans. Whereas Chapter 1 estimates the effect of the average mandate on premiums, Chapter 2 focuses on a specific mandate, one that requires insurers to cover prostate cancer screenings. The focus on a single mandate allows a broader and more careful analysis that demonstrates how health policies spill over to affect the labor market. I find that the mandate has a significant negative effect on the labor market outcomes of the very group it was intended to help. The mandate expands the treatments health insurance covers for men over age 50, but by doing so it makes them more expensive to insure and employ. Employers respond to this added expense by lowering wages and hiring fewer men over age 50. According to the theoretical model put forward in the chapter, this suggests the mandate reduces total welfare. Chapter 3 shows that the employer-based health insurance system has deterred entrepreneurship. It takes advantage of the natural experiment provided by the Affordable Care Act's dependent coverage mandate, which de-linked insurance from employment for many 19-25 year olds. Difference-in-difference estimates show that the mandate increased self-employment among the treated group by 13-24%. Instrumental variables estimates show that those who actually received parental health insurance as a result of the mandate were drastically more likely to start their own business. This suggest that concerns over health insurance are a major barrier to entrepreneurship in the United States. / Economics