We had an annual travel insurance plan - at the end of March we had to cancel a trip to Italy because my girlfriend's mum had to go for a major heart operation. We had cancelled all the bookings that we could on Agoda and whatever else which still had a free cancellation option, but there were certain things that we couldn't cancel, such as our flight tickets, one hotel and a train ticket. We had called up Tune Protect to check whether we would be able to get this covered by our travel insurance plan. The customer service person said that we could and that we would need to submit our application after the planned departure date.
So when things settled down after my girlfriend's mum's operation, we put together the necessary documents and prepared them nicely to make it as easy as possible for the claims team.
After two weeks, we didn't hear back, there was no email or anything, so we called to follow up. The team said that they are looking into it and they will get back to us. After another two weeks after that, we still hadn't heard back, so I texted a friend of mine who works at Tune Protect to get his help (which was something I didn't want to have to ask a personal favour for). After a couple of days, someone from the claims department reached out to us and requested for all the same documents that we had already submitted. This was a little bit frustrating, but we just went through that process and submitted all the same documents that we had originally submitted online.
After about another 10 days or so, we got an email saying that our claim had been approved and we would be refunded the total amount that we were seeking. We received our payout into our bank account maybe another week or so after that.
Make sure both you and your travel partners' names are on all the travel bookings, just to make it easier for the claims process. For example, for the Agoda booking, you can register a guest to do that so that if anything happens, it's easier.