Ransomware’s explosion and its worsening damage, including stolen data and destroyed backups, has upended insurance coverage and prompted a substantial rise in wrangling over claims. We distill the insights offered by cyber insurance leaders during a panel at Cybersecurity Docket’s recent Incident Response Forum, as well as in our conversations with them. Our coverage includes questions that companies should ask insurers about coverage before and during ransomware incidents, how to navigate claims negotiations, and how insurers have increased scrutiny of companies’ ransomware prevention efforts. See “Managing Ransomware’s Mutation Into a Public Data Breach” (May 6, 2020).