I have a fun one: I booked a reservation using points for a location that has since temporarily closed. After no follow-up from Hertz's Twitter team, I called the PC line and was offered to make a new reservation at another (less convenient) location. For some reason, however, the rep had to transfer me to someone else to cancel the old reservation (but she was able to make a new points reservation first even though my remaining balance, before canceling the old reservation, was insufficient).

I checked my Hertz account yesterday and, while I got my points back from the canceled reservation, they were never debited for the new one. I did notice an "RQ" code in my new reservation, which I am not sure if that impacts the points. I tried to modify my reservation (making sure to select a point redemption option) and it didn't change anything.

Hoping Hertz doesn't come after me for the cash price of this rental ($1,000+) after some accountant notices there was no compensation.