The purpose of this research is to better understand community housing resilience and the role of insurance using a Build Back Better Long-term Recovery Housing framework to analyze approaches and effects on long-term housing rebuilding and recovery. A comparative case study approach is taken to assess insurance policies and outcomes following Hurricane Katrina in New Orleans and the Canterbury earthquake sequence in Christchurch, New Zealand, both affluent urban communities with strong insurance markets. Framed within the context of “Build Back Better”, the community housing and insurance resilience assessment is based on five key indicators; governance, community resources, risk reduction, housing rebuilding funding (funding and speed of funding), and time compression (built environment and periods of recovery time). Public and private insurance schemes for both case studies are identified and are considered together with analysis of insurance claims and other sources of financial support. The findings and results show that recovery is the result of highly interdependent Build Back Better processes. The data suggests that insurance and governance systems greatly influences the onset and overall speed of recovery (time compression), thereby performing a major role in long-term recovery. This research provides an original contribution to disaster recovery knowledge by analyzing insurance claims from two well-documented natural disasters. Additionally, the paper proposes for the singular definition of community housing resilience.