African Americans start smoking later in life, yet they are less likely to quit smoking than other racial/ethnic groups. Drawing upon 40 in-depth interviews with former and current Black women smokers in the South Side of Chicago, this study examines external barriers to successful smoking cessation among socioeconomically disadvantaged Black women smokers. Beyond individual factors (e.g., stressors), this study finds interpersonal and structural factors that influence Black women's cessation efforts, including the high prevalence and normality of smoking and access to cheaper, loose cigarettes in their communities. Findings highlight the importance of considering local contexts for future tobacco research and policies.