Drawing from the social convoy model, this study investigates whether the nature of retirement (voluntary or involuntary) influences loneliness among retirees, and how different social support types may affect this association. Data come from the 2014 Health and Retirement Study ( N = 2,055). Five social support types were identified: weak, ambivalent, strong positive, children strain, and family strain. Involuntary retirement was associated with a higher level of loneliness; however, involuntarily retired individuals with strong positive social support had a relatively lower level of loneliness. Findings from this study suggest that social support may alleviate the negative impacts of involuntary retirement. Our research provides a theoretical basis for developing a practical program to reduce the negative impacts of involuntary retirement on well-being.