Attachment theorists have frequently highlighted the adaptiveness of so-called “insecure” patterns of attachment to adverse and unsafe contexts, but the same understanding has rarely been extended to “insensitive” caregiving. Caregiving has often been seen in linear, good/bad terms, as the ability or otherwise of the parent to provide a safe-haven to the child. Without development, this understanding of parental caregiving loses the potential of attachment theory to highlight the challenges posed by the external context in which a parent seeks to protect their children, and the ways this shapes the internal meaning the parent gives to their caregiving experiences. In this chapter, the Meaning of the Child Interview (MotC) is used to develop an understanding of non-sensitive caregiving as a series of implicit and explicit compromises that parents make to safeguard their child and manage the outside world. These compromises that are informed by their past and present experiences of danger, including the threats inherent in unequal social conditions and power relations, and contain both child-protective and self-protective elements. A case example based on interviews with parents of a child with a diagnosis of autism and his brother is used to illustrate the systemic and clinical potential of the theory.