The most unexpected cyber claim I've seen covered was tied to a business email compromise (BEC) attack. A client had their accounts payable clerk tricked into wiring money to what appeared to be a trusted vendor. On the surface, it didn't feel like a "cyber" issue—there wasn't malware or ransomware involved, just a convincing phishing email. However, because their policy included social engineering coverage, the loss was reimbursed. Watching that claim go through opened my eyes to the breadth of cyber risks, beyond the typical "hackers in the network" scenarios.
Since then, I've always recommended that clients double-check their policies for social engineering and wire fraud coverage. Many assume their standard cyber policy has it, but I've seen firsthand that's not always the case. That one situation made me much more direct in urging businesses to read the fine print and ensure their coverage aligns with how cybercriminals are actually targeting companies today.