Based on recent findings that post-retirement adjustment may be influenced by the conditions leading up to the decision to retire, we examine the impact of individual agency in the retirement decision on problematic drinking behavior, as well as the extent to which such an effect may itself depend upon the valence of the pre-retirement work experience. Using a sample of 304 blue-collar retirees, our findings indicate that, when controlling for pre-retirement drinking behavior, perceptions of retirement as the result of a more forced or involuntary decision are associated with greater alcohol consumption, while perceptions of retirement as the result of a more volitional or voluntary process are associated with lower levels of alcohol consumption and a lower risk of problematic drinking behavior. Our results also indicate that pre-retirement job satisfaction amplifies the former relationship, while attenuating the latter one.