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Most Americans have health insurance coverage through an employer—their own, their spouse’s or their parents. In addition to wages, then, a job loss can also mean instability in health insurance coverage. In this paper, I examine the multiple ways that losing one’s health insurance after a job loss can lead to financial trouble. Rather than just losing income, losing a job means finding new health insurance coverage or going without. I draw on interviews with 34 women having trouble paying for their healthcare. I find that institutional arrangements typical of insurance—yearly deductibles and out of pocket maximums, in-network and out-of-network providers, and high premiums for plans purchased outside of a workplace—represented significant expenses for respondents on top of lost wages. Changing jobs, no matter whether voluntarily or not, led to financial hardship because of the extra expenses associated with paying for their healthcare. In an era of high job turnover and employment instability, the connection between work and healthcare becomes even more problematic, especially for those with ill health, disabilities, or chronic conditions.