Pluvial flooding in urban areas is one of the most significant drivers of disaster loss in Canada. Damages during pluvial flood events are associated with overwhelmed urban drainage (stormwater and wastewater) systems. During the period from 2013 to 2021, Canadian property and casualty insurers reported approximately CAD 2 billion in personal property (residential) pluvial sewer backup claims during flood catastrophes. There has been growing interest in managing pluvial urban flood risk, notably through newly funded national programs focused on climate change adaptation. These programs have included the development of new guidelines and standards focused on managing the underlying factors contributing to urban and basement flooding. Inflow and infiltration (I/I) has received limited attention in the pluvial flood literature, however. Informed by significant engagement with practitioners in Canada, this paper provides a review of the issue of I/I into wastewater systems and its relation to pluvial flooding. The paper will address concerns related to private property engagement in I/I and urban pluvial flood reduction programs. Both improved technical standards and administrative support are needed to ensure that wastewater infrastructure is less susceptible to I/I over its lifecycle.