This paper examines policy and ethical implementation issues associated with local drug policies that are aimed at producing a "least harm" approach toward youth, with particular application to tobacco policy as an example of a legal, but addictive drug. Research is reviewed which shows the inconsistencies between federally mandated enforcement of zero tobacco use, the Synar Amendment and local community and school policies which appear to relax enforcement of no-use policies for the purpose of retaining youth in school. The inconsistencies are described from the perspective of a "least harm" approach, in that tobacco use may be considered less harmful than absence from school, or use of other substances. The conflict between law and intent to reduce harm is examined with implications for long-term enforcement of federal policy, and for effectiveness of tobacco and other drug abuse prevention programs and other drug policies. Several strategies for reducing the conflict are recommended. These include provision of support-orientated smoking cessation programs for youth on school campuses and in community organizations, and promoting consistent no-use norms across all drugs and across multiple channels that affect youth-mass media, school, point-of-purchase settings and public settings and events.