Our objective was to determine how point-of-sale tobacco marketing may relate to sales to minors. The authors used data from a 2007 cross-sectional study of the retail tobacco marketing environments in the St. Paul, MN metropolitan area matched with a database of age-of-sale compliance checks (random, covert test purchases by a minor, coordinated by law enforcement) of tobacco retailers and U.S. Census data to test whether certain characteristics of advertising or neighborhoods were associated with compliance check failure. The authors found that tobacco stores were the most likely type of store to fail compliance checks (44% failure), supermarkets were least likely (3%). Aside from a marginally significant association with Hispanic population proportion, there was no other association between either store advertising characteristics or neighborhood demographics and stores’ compliance check failure. Though our findings were null, the relationship between advertising and real youth sales may be more nuanced as compliance checks do not perfectly simulate the way youth attempt to purchase cigarettes.