This case study examined the implementation and enforcement of the purchase, use, and possession (PUP) laws for tobacco in four Kentucky communities. Purposive and snowball sampling were used to identify 44 adult key informants. Qualitative, semistructured phone interviews assessed knowledge about PUP laws, enforcement, effects of the laws on teen tobacco use, and perceptions about the laws. Seven themes were identified: enforcement not a priority, unaware of enforcement authority, spotty enforcement, other sources of tobacco, minimum penalties, confusion about compliance checks, and schools as de facto enforcers. One community went beyond the statutory requirements of the law and created more stringent penalties for violating the use and possession law, and it also had low illegal sales rates. These laws may be more effective if they are enforced strictly with a meaningful penalty and a clear enforcement strategy.