Great question. The good news is that insurance is regulated by States and not the Federal Government. Provided the insurance company has sufficient liquidity to pay claims, most regulators allow a wide range of investment for insurance reserves. Captive Insurance Companies normally have an investment policy statement (IPS) that is approved by the insurance regulator at the state level. Bitcoin or other cryptocurrencies could be included in the IPS and owning them would be justified since potential claims in the future might require cryptocurrencies for payment. Bottom line - many captive regulators would approve holding some Bitcoin.
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You are right and more about the recent Virus like WannaCry or the most recent of them Petya, that are asking the “rewards” on Bitcoin. I think that they are or are going to be into Cryptos, basically, Bitcoin in other to paid to some of their clients. And as the risk is out there will be insurance policies on Bitcoin. Regardless of the regulations. Very interesting