From a role theoretical perspective, it can be expected that individuals differ in the extent to which they experience aspects of the work role after they have fully retired from it. This study presents a measure of these “postretirement work role residuals” and examines them in relation to structural preretirement factors, psychological preretirement factors, and the nature of the retirement transition. Heckman selection models were estimated based on three-wave panel data collected among 848 older Dutch individuals who were employed at Wave 1 and fully retired thereafter. Although for the majority of retirees prior work plays only a minor role in their current lives, also for a considerable share prior work is still important. Higher levels of postretirement work role residuals were observed among those who expected to miss work-related social status in retirement, who were less disengaged from work in preretirement years, and among those who retired involuntarily.