CDW Claim Experience
So I rented car from Sixt in Switzerland. Unfortunately I managed to dent a door and brake off the mirror in the hotel garage. It was my stupidity and no one else was involved. I had to switch cars for the reminder of my trip / rental period in nearest location.
After I came back I called Chase Sapphire Reserve benefits administrator. (just call the number on your card they will transfer you). They took down some basic info and sent me an email with instructions. You can mail stuff in, or email it, or file the whole claim online. I went for option three. Over a period of about two weeks I collected all the paperwork they requested from Sixt and uploaded the documents the the claim website.
In the meantime, Sixt charged my credit card for the damage for ~$4300.
About 5 days after I uploaded all the documents the benefit administrator responded via email and asked me for proof of payment for the damage, also stating that if I did not pay for it yet, the will. I supplied printout of the credit card activity from chase with the said charge and three days later, when I checked online it said the check is in the mail.
The check I received was $125 dollars less than what Sixt charged me. I'm not sure why that is. Maybe different currency conversion??? I have no clue, might call them and ask, but I'm pretty happy I got the check. Plus extra ~13000 or so points from Chase, since the charge is for 'car rental'
One piece of advice is to save, or make copy / take a photo of every little piece of paper that is in any way related to your rental and the damage. I had to request some missing paperwork from Sixt. They responded quickly, being Swiss and all, but I can imagine that you might have a hard time getting paperwork from some other countries.
Overall positive and quick experience with CDW insurance on the card. This benefit saved me a lot of money over the years and now that I experienced it first hand it's an additional piece of mind.