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Decades of research shows that small firms are much less likely to offer health insurance than large firms, but less is known about differences among small employers. We examine this issue using the Medical Expenditure Panel Survey-Insurance Component with Administrative Records (MEPS-ICAR), a unique employer-employee linked data set that is constructed by matching the Medical Expenditure Panel Survey-Insurance Component (MEPS-IC) to Internal Revenue Service administrative records and the Decennial Census. Multivariate analyses show that among firms with fewer than 50 workers, the probability that workers receive an insurance offer is positively associated with higher median workforce incomes, and conditional offers of dependent coverage increase when the majority of workers are married or from a family with at least three members. This first application of the MEPS-ICAR highlights the significance of workforce characteristics in shaping small employer insurance benefits and the data’s usefulness for expanding analyses of policy changes, wage-benefit tradeoffs, and health insurance benefits. [ABSTRACT FROM AUTHOR]