Crop insurance loss data can illuminate variations in agricultural impacts from exposure to weather and climate-driven events, and can improve our understanding of agricultural vulnerabilities. Here we perform a retrospective analysis of weather and climate-driven reasons for crop loss (i.e. cause of loss) obtained from the Risk Management Agency of the United States Department of Agriculture. The federal crop insurance program has insured over $440 billion in liabilities representing farmers' crops from 2001 to 2016. Specifically, we examine the top ten weather and climate-driven causes of loss from 2001 to 2016 across the nation comprising at least 83% of total indemnities (i.e. insurance payouts provided to farmers after crop loss events). First, we analyzed the relative fraction of indemnities by causes of loss, over different spatial and temporal resolutions. We found that drought and excess precipitation comprised the largest sources of crop loss across the nation. However, these causes varied strongly over space and time. We applied two additional normalization techniques to indemnities using (1) insurance premia and the gross domestic product implicit price deflator, and (2) liabilities to calculate the loss cost. We conducted trend analyses using the Mann–Kendall statistical test on loss cost over time. Differential trends and patterns in loss cost demonstrated the importance of spatio-temporal resolution in assessing causes of loss. The majority of monthly significant trends (p < 0.05) showed increasing loss cost (i.e. increasing indemnities or decreasing liabilities) in response to weather events. Finally, we briefly discuss an online portal (AgRisk Viewer) to make these data accessible at multiple spatial scales and sub-annual time steps to support both research and outreach efforts promoting adaptation and resilience in agricultural systems.