Can I cancel and re-book My trip to reset the pre-existing conditions deadline?

We don’t get this question a lot, but nearly every time we do it’s because a traveler has been advised by their travel agent that they should cancel and re-book their trip so travel insurance will cover their pre-existing conditions. In other words, the clock is reset so the person can buy travel insurance within the pre-existing conditions’ waiver deadline.

Insurance companies are not stupid. All the travel insurance plans I know of address this somewhere in their terms and conditions. They usually have some kind of a phrase that’s along the lines of “this booking must be the first and only booking for the same travel destination and dates”. The travel insurance companies have already anticipated that this advice is out there and they’ve covered it within their policy wording.