This paper considers the increased incidence of insecure job conditions for young individuals entering the Italian labour market and their chances of moving to a more secure job after a reasonable period of time. In particular, we investigate empirically whether and how long-term changes in labour market institutions and conditions have altered the role of the family of origin in both labour market entry and subsequent transitions. We use the Italian Households Longitudinal Study (Ilfi) and show that employment opportunities have changed significantly in Italy over the past three decades (from the late 1970s to the early 2000s). For an increasing share of young adults precariousness extends over a fairly long period of their working life. The family of origin reduced the probability of insecurity both in the early 1980s and during the 1990s, but in a different way: in the early 1980s, it had an effect in the entry year, but not subsequently; after the implementation of the Treu reform, its effect appeared only in the years following that of entry. Our overall results suggest that the rapid expansion of insecure contractual arrangements in the 1990s-early 2000s has increased the difficulty of transitioning to a “better” job condition (i.e. secure employment). This has enhanced the role of the family of origin in overcoming the difficulty and generated new inequalities among young Italians.