This article looks at how retirement timing is changing in Italy. A first aim is descriptive and it is to identify recent trends in retirement age, following the pension reform. Then the focus is on factors which may favour or hinder the extension of the working career of older workers. They are studied by looking at the reasons for retirement, introducing the distinction between voluntary and involuntary retirement, and some predictors of retirement. Some of them relate to the work history of individuals, in particular the stability/instability of careers due to episodes of unemployment. The level of education and gender, two variables that may affect the employability of older workers, have also been considered. The study is based on a longitudinal analysis (Kaplan–Meier survival estimates of transition to retirement and binomial logit discrete-time model for the analysis of retirement predictors) of the Survey of Health, Ageing and Retirement in Europe (SHARE) Job Episodes Panel data. They refer to a sample of 1,999 individuals born between 1911 and 1959. Although the various pension reforms initiated in Italy in the 1990s have not yet been fully implemented, retirement age is rising, even in the case of involuntary retirement. Regarding work history, the advantages of a working career with a small number of unemployment episodes emerge from the study.