Individual state approaches to assisted living/residential care (AL/RC) licensing and oversight in the United States result in different practice standards and requirements, including psychotropic medication use. We examined 170 psychotropic medication deficiency citations issued to 152 Oregon AL/RC settings from 2015 to 2019. Applied thematic analysis resulted in the following themes: (1) documentation issues are primarily responsible for noncompliance, (2) unclear parameters place direct care workers in a role paradox, and (3) there is a persistent disconnect about when to seek qualified expertise before requesting psychotropic medications. AL/RC-specific mechanisms for medication prescription and administration are necessary to improve the structure and processes of care. Policymakers might consider how regulations unintentionally incentivize task-oriented versus person-centered care practices.