In ageing societies, it is not uncommon to enter grandparenthood while one's own parents are still living. Thus, a pertinent question is whether it matters for provision of help to parents if adult children have grandchildren they look after. Earlier studies addressing help to more generations conclude that providing help to one generation increases the likelihood of helping another, and not the contrary. Here, we investigate whether gender and welfare state context make a difference for this finding by using data from the Survey of Health, Ageing and Retirement in Europe and the Norwegian Life course, Ageing and Generation study. The 14 countries included represent four different care regimes. Overall, we find that adult children who have grandchildren they look after on a weekly basis are more inclined to provide weekly help and care to parents compared to those without such frequent grandchild care responsibilities. However, the results suggest that gender and care regime matter. Helping more generations seems easier in some contexts than in others, and the contrasts across regimes are considerably greater for women than for men. When there are few alternatives to family care, many (women in particular) may have to prioritise which generation to help.