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The Centers for Medicare & Medicaid Services approved a Section 1115 Medicaid demonstration waiver in Kentucky that will require some Medicaid beneficiaries to work or fulfill qualifying community engagement activities to retain Medicaid coverage. In this brief, we investigate the work patterns of working Medicaid beneficiaries in Kentucky who are nonelderly, nondisabled, and who do not appear to qualify for student or caregiver exemptions and are therefore potentially subject to Medicaid work requirements. Among this enrollee group, we highlight workers who are (a) working at least 48 weeks a year and at least 20 hours a week and are likely to satisfy the work requirements year round, (b) working at least 960 hours annually (the total required to satisfy the waiver year round) but not consistently throughout the year and therefore may not satisfy the work requirements year round, or (c) working less than 960 hours annually and will need to either work more or fulfill additional qualifying activities to satisfy Medicaid work requirements year round. We also assess the potential access to employer-sponsored insurance coverage and the average annual employee contributions to employer-sponsored health insurance plans in Kentucky facing workers by firm size and by the share of low-wage employees in the firm. We find that the structure of Kentucky’s Medicaid waiver does not seem to align with the reality of some working enrollees’ lives and that working enrollees losing coverage may not have access to an employer plan, let alone one affordable to them.