The present study analyzed retirement intentions and behavior as part of a work role withdrawal process. We examined the influences of the organizational and group contexts in the process of work role exit by means of two sources of work role expectations: human resource practices and group norms. Three different types of human resource practices were taken into consideration: performance enhancement practices, retirement enhancement practices, and organizational pressures toward retirement. Furthermore, three types of retirement indicators were analyzed: age considering retirement for the first time, early retirement intentions, and retirement age. Hierarchical regression analyses were carried out on a sample of 270 retirees to test the hypotheses. Results showed that retirement enhancement practices and organizational pressures toward retirement predict all the retirement indicators. Moreover, group norms moderated the relationships between retirement enhancement practices and two out of the three outcomes: age considering retirement for the first time and retirement age. Overall, our findings showed that organizational and group contexts play an important role in the retirement process. Moreover, our results indicate an interaction between organizational and group factors in the work role exit process.