In January 2018, the Centers for Medicare & Medicaid Services approved Kentucky’s Section 1115 demonstration waiver, which allows the state to require some enrollees to participate in work or community engagement activities to retain their Medicaid coverage. We estimate the number of nonelderly adult Medicaid enrollees in Kentucky, statewide and by region, who are: likely exempt from the waiver’s work requirements; potentially subject to the waiver’s work requirements and already working; and potentially subject to the waiver’s work requirements and not working. For each group, we assess characteristics that may pose barriers to documenting exemptions, obtaining and maintaining employment, or monthly reporting of completed hours. We estimate that about 174,000 enrollees are likely exempt from the waiver’s work requirements, 169,000 enrollees are potentially nonexempt and working, and 188,000 enrollees are potentially nonexempt and not working. Among enrollees who are potentially nonexempt and not working (and, as a result, who are at highest risk of losing Medicaid coverage), we find that nearly half are above age 50, a quarter are less than high school educated, more than 2 in 5 have serious health limitations, and more than a quarter report having no internet access. These findings suggest that many of these enrollees will have difficulty finding work, participating in community engagement activities, and documenting their fulfilled hours.