At the insurance company I worked for for 2 years I have enough stories to fill a whole subreddit.
One that sticks in my mind was someone who clearly did not understand the way insurance works.
I worked on the sales and service side of the business for a home insurance provider and once had a man transferred through from the claims team as he was adamant he had a policy with us but the claims handler could find no evidence of it.
It took all of 2 minutes for me to discover that he had taken a policy out with us 6 months prior and had defaulted on his direct debit 3 times so following the standard letters of warning we had cancelled the policy about 2 months after he took it out.
He openly admitted that he didn’t want to pay the premium so had cancelled his direct debit, but because he had been sent policy documents when he took the policy out, he was under the impression that he would still be covered for the catastrophic flood that had ripped through his home after a pipe burst at some point during his 2 week holiday.
It then took me 45 minutes to get it through to him that the company was not going to pay out the tens of thousands of pounds it would cost to repair his home and replace his contents, and maybe he should have thought about the bigger picture before deciding the £33 per month payment was ‘not worth it’
Hindsight is 20/20 I guess.