Objectives. We evaluated the feasibility, acceptability, and effectiveness, in addition to the effects of a psychoeducation-based orientation on smoking cessation knowledge for Courage to Quit (CTQ), an evidence-based smoking cessation intervention disseminated to racially diverse, urban community sites in Chicago, Illinois. Methods. Smokers (n = 1494; 55% African American) enrolled in 6-session full (n = 945) or 3-session short (n = 549) versions of CTQ in 2008 to 2012. Results. Orientation improved knowledge of efficacious and nonefficacious treatments. Acceptability was outstanding: more than 90% of participants would recommend CTQ. Feasibility was good: completion rates were 53% in the full and 75% in the short programs. Intent-to-treat quit rates were 19% in the full and 17% in the short programs (completer quit rates were 36% and 22%, respectively). Among completers, smoking cessation medication use was associated with higher quit rates. There were no racial disparities: African Americans and Whites showed similar completion and quit rates. Predictors of successful quitting were higher readiness to quit and smoking cessation medication use. Conclusions. CTQ is moderately successful in the short term as delivered in community-based settings for urban-dwelling, largely minority smokers. Further evaluation of longer-term outcomes and cost effectiveness is warranted.