Researchers are only beginning to investigate how to measure a community's readiness to engage in an intervention. In this study, we investigated the readiness of police departments to deal with tobacco policies about youth access to tobacco and youth possession of tobacco. Police officers in 24 towns completed structured interviews designed to assess each police department's community readiness to enforce tobacco sales and possession laws. Community readiness ratings were compared to outcome measures in the community, such as tobacco sales and possession enforcement activity, youth knowledge of such activities, and youth reports of smoking history. Higher readiness ratings on the youth tobacco possession enforcement scale was related to higher youth possession citation rates, higher number of youth reporting knowing someone who received a possession ticket, and a smaller number of youth reporting seeing minors smoking in their community. Youth in communities with higher possession readiness ratings in Efforts and Knowledge Regarding the Efforts had lower reports of youth reporting ever having smoked. Higher readiness ratings in the Leadership dimension of tobacco sales enforcement was related to lower tobacco commercial sales rates in the community. Higher tobacco sales readiness ratings in the Efforts, Knowledge Regarding the Efforts, and Knowledge Regarding the Problem dimensions were related to a lower number of youth reporting ever having smoked. The implications of these findings are discussed.