Background: The vast majority of demographic studies have approached and operationalised the notion of economic uncertainty using snapshot indicators. Hence, the complexity and diversity of individuals’ employment careers were largely hidden. We posit that the persistence of joblessness – that is, repeated and close spells of joblessness – represents a crucial marker of economic uncertainty in the realm of fertility (intention) research. Objective: We aim to explore the association between persistent joblessness of both members of the couple and women’s fertility intentions among those who entered employment at least once in the last five years. Methods: We develop an index of persistent joblessness that simultaneously considers individual and contextual labour market conditions. It accounts for the severity of the experience of joblessness, the chances that an individual will escape joblessness, the alleviating effects of the years spent in continuous employment, and the recentness of any joblessness experience. This index is operationalized for Italy by consulting the 2009 Family and Social Subjects Survey. We verify the association between the index and women’s fertility intentions among Italian couples, net of a series of confounders. Results: Our findings show that the higher the level of persistent joblessness, the lower a woman’s fertility intentions. Within couples, we found a gendered association between joblessness and fertility intentions: His joblessness, more than hers, seems to play the decisive role in inhibiting a woman’s fertility intentions. Contribution: We corroborated that joblessness inhibits positive fertility intentions and facilitates negative fertility intentions. But we also added that these associations are much more pronounced when joblessness has been persistent. Disregarding the role of persistence in joblessness, scholars might underestimate the importance of individual-risk factors linked to labour market biographies in fertility planning. We additionally illustrated that accounting for regional labour market dynamics, thus placing one’s own level of persistence in joblessness in context, is pivotal.