There has been significant interest and progress in understanding the role of caregiver-child unpredictability on brain maturation, cognitive and socioemotional development, and psychopathology. Theoretical consensus has emerged about its unique influence in shaping children’s experience, distinct from other adverse exposures or features of stress exposure. Nonetheless, the field still lacks theoretical and empirical common ground due to difficulties in accurately operationalizing and measuring unpredictability. In this paper, we first provide a historical overview of unpredictability and present four issues that are currently under-discussed but are crucial to the field. Focusing on how moment-to-moment and day-to-day dynamics are at the heart of caregiver unpredictability, we review three approaches aiming to address some of these nuances: dynamic systems, environmental statistics, and entropy. Lastly, we conclude with a broad summary and suggest future research directions. Systematic progress in this field can inform interventions and policies aiming to increase stability in the lives of children.