While the literature has widely shown that the provision of childcare by grandparents is often crucial for young mothers’ participation in the labour market, this work investigates the link between grandmothers’ participation in the labour market during adult life (between ages 18-49) and their provision of grandparental childcare later in life. Two contrasting theoretical arguments are plausible in this respect. On the one hand, lifelong homemakers could be more family-oriented and more likely to provide grandchild care in later life. On the other hand, ever-employed grandmothers could be more likely to have employed daughters, and provide grandchild care to support their working careers. With data from the Multipurpose surveys on Families and Social Subjects (2003, 2009, 2016), we estimate logistic regression models, considering various specifications of grandparental childcare, and measuring labour market attachment in three different ways (having ever worked, length of working career, employment interruptions for family reasons). Results show a positive association between grandmothers’ labor market attachment and grandparental childcare provision. A strong dualism emerges between grandmothers who ever worked and those who never did, with the former more likely to provide grandparental childcare, especially when parents are at work. Grandmothers who worked only a few years are more similar, in terms of grandchild care provision, to those who worked throughout their life, than to lifelong homemakers. Comparing Italian macro-areas strengthens our conclusions: differences between ever- and never-employed grandmothers are present in whole the country, but this holds especially in Northern regions, where the higher female participation to the labour market amplifies the need for grandparental childcare. Overall, we showed that intergenerational family solidarity is activated throughout the country, but it is evident that in a context of growing female labour fo