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Travel insurance remains a mystery to me...

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I feel like I always have to have a topic about insurance at least once a year, so here goes again...

I still -- even after getting it a handful of times -- don't completely understand the logic behind what part of the trip you're supposed to be insuring when you purchase travel insurance.

All signs point towards the 'non-refundable' aspects of your trip...so, anything you'll pre-pay by the time you leave that you risk losing completely if you have to cancel.

That all makes senses, but talking to TravelGuard last week I was a bit confused about their tactics on how to go about this. They seemed to indicate that I should purchase a policy as soon as I pay my first pre-paid cost (that would be one hotel, in our instance). It was important time-wise if I recall to do this within a certain amount of time of the first payment for the trip. But obviously there will be many more pre-paid costs to be incurred for our trip in the coming months and before we leave in December. Their response was to just keep 'adding on to the policy' each time we have a new prepaid cost.

That, obviously, seems weirdly inefficient and sort of silly to me. But wondering how others have handled this.

What's clear is that we're only really paying to insure prepaid costs and not, for instance, hotels that are cancelable 24hrs in advance.

Thanks in advance for any advice and/or first-hand experience here.

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