This article focuses on multiple conditionalities in benefits and housing from the perspective of lone parents in Ireland. The Irish case echoes historical experiences elsewhere and is offered not as an exceptional or extreme case but as an in-depth single case study and a lens for comparison. Although contemporary forms and combinations of conditionalities are new to Ireland, the experience of multiple conditionalities in benefits and housing is not new. Hence, a historical perspective is used to examine contemporary multiple conditionalities in benefits and housing. In the past, conditional regimes for lone parents were justified in terms of moral reformation for first time mothers and avoiding moral contagion of mothers with subsequent pregnancies. In contemporary times, in the case of employment, lone parents are problematised as working part-time and “nesting” on in-work-benefits, and in the case of homelessness, lone parents who prioritise the security of tenure embedded in social housing are accused of “gaming” the system. While acknowledging ambiguities, the paper finds the overlap of welfare and housing discourses contribute, intentionally or unintentionally, to epistemological foundations or understandings of lone parents, shifting public perceptions, and framing them as “problems” to be solved. They simultaneously temper lone parents' expectations. Increased precarity and disempowerment is associated with dual conditionality, and ontological uncertainty is multiplied when experienced cumulatively across employment, social protection, and housing regimes in a context of generally poor public services and labour market precarity and in the historical context of stigmatisation. Nonetheless, lone parents demonstrate considerable agency.