To the OP, that is bad luck, and I hope that the surgery happens quickly. I would wait until the last minute before cancelling things, but only if the delay doesn't make it more expensive. So if you could cancel the hotel for free today, but not next week, then you should make sure to minimize losses. The insurer should pay for reasonable losses from the cancellation, but will complain if you have made the situation worse. That is the reason for the gall bladder exclusion, they are essentially liable for the cancellation fees, but not necessarily the expensive overseas surgery and repatriation should you decide to travel anyway, once you were aware of the potential for the problem to happen. But I don't think they can use the exclusion to avoid their responsibility for cancellation fees for something that wasn't pre-existing at the time the policy was purchased. But aside from cancellation related costs, they don't have an obligation to provide medical advice or costs prior to the departure date. Usual disclaimer here, as I'm not a lawyer, or an expert in the insurance industry.