If you make any travel plan upgrades or add services or extensions to your trip, don’t forget to update your travel insurance coverage. Yes, it will take some extra effort on your part and will involve an expense but if there are problems, you want to get your full refund.
If you purchase a $300 upgrade to your accommodations, you will likely pay $25-35 to have this added to your plan. Isn’t it worth that amount to ensure that you will get a full refund?
If your original plan had features (like cancel for any reason) that had to be purchased within a certain number of days after booking the trip, the same rules apply to your add on.