Introduction: Smoking remains the leading cause of preventable death in the United States. Many smoking cessation guidelines advise smokers to quit precipitately; however, most quit attempts involve a more gradual cessation. Characteristics of individuals who tend to reduce prior to quitting and the effectiveness of pre-quit reduction are not well understood. This study examined individual differences and smoking cessation outcomes between individuals who self-initiated gradual reduction in cigarettes per day (CPD) and those who did not reduce prior to quit date. Methods: This study is a secondary analysis from a randomized clinical trial of smoking cessation with pharmacotherapy among individuals under community corrections supervision. We compared participants who self-initiated smoking reduction by at least 25% between baseline and the first treatment session (n = 128) to participants who either increased or did not reduce smoking between baseline and the first treatment session (n = 354). Results: African American race, no previous cigar smoking, no previous use of pharmacotherapy for smoking cessation, less withdrawal symptoms at baseline, and older age at first smoking were associated with being a self-initiated gradual reduction in univariate analyses. Individuals who self-initiated gradual reduction also had a had a greater likelihood of achieving at least one quit during the one-year study period as compared to those who did not reduce prior to the intervention. Conclusions: Individuals who self-initiate gradual reduction differ from those who increase or do not change their smoking prior to a quit date. Gradual reduction also increased success in quitting.