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As critical infrastructure systems consider whether and how to adapt and build resilience to climate variability and change, more research is needed to holistically explore the dynamics of resilience-building changes over time. We begin to fill this gap with a case study of the Rhode Island public wastewater sector. The Rhode Island Department of Environmental Management has invested significant funding, technical assistance, capacity building, and regulatory pressure to help publicly owned wastewater systems build resilience to climate challenges since 2010. To trace, assess, and understand the dynamics of resilience-building efforts over time, we interviewed wastewater utility and municipal personnel using event history calendars (EHCs). EHCs helped respondents recall details of relevant events, including potentially disruptive storms/incidents, and how they responded, including large- and small-scale adaptations, during the study period (2010–2023). We used EHCs to trace resilience and transformation capacities over time, and to analyze and predict movement toward transformational adaptation. We found that factors that best enable movement from incremental to transformational changes include unlocking capacity, or the organizational cultural value of in-depth learning/change, and a suite of contextual supports – new information, forward-looking collaborators, and stable funding sources – which require buy-in across levels of governance. We also found that, with organizational culture considered, experiencing disruption is not predictive of pursuing transformative adaptation. This suggests decision-making strategies for states, local jurisdictions, and utility managers to support climate adaptation and resilience in critical infrastructure, such as eliminating path-dependencies and silos, lowering thresholds for action, and leveraging networks to support moving toward transformation.