Labour market disadvantages tend to run in families: children who grow up with parents who experience job losses or receive low wages are themselves at higher risk of experiencing labour market difficulties. However, little is known about the intergenerational transmission for those who manage to escape from precariousness, and how the transmission of labour market disadvantage operates depending on the gender structure of parent-child dyads. The present study uses Swedish register data and longitudinal methods that follow a cohort of people born in 1985 (n = 72,409) and their parents across 26 years. Our findings show that children who experienced parental employment disadvantages had the most severe labour market disadvantages later in life. However, if the employment situations of their parents improved, they were somewhat more likely to follow a more stable, high-wage career path compared to children whose parents experienced more persistent forms of disadvantage, such as long-term unemployment or severe labour market instability. We also show that the mother's labour market disadvantages were an important determinant of the future labour market career of her child, regardless of gender. This finding underscores the need to go beyond the analysis of father-son dyads in intergenerational research.