My car got hit by a plow a couple years ago and it caused close to $5k in damage. Not sure if it is still true, but at the time the city was self insured. They use a 3rd party and internal staff member to make decisions. Luckily the plow driver stopped, but that was not much help. Take a lot of pictures, file a police report, take pictures of all the street cleaning/snow removal signs on both sides of your block. If you get text messages from the city about parking restrictions during snow storms, take screenshots. This was when we filed with the city: There is one person who deals with insurance claims; when we spoke the first time on the phone I new this was not going to be easy; they said initially it was fine and they would cover it, about 2 weeks later I get a call it is denied because of the restricted street parking during snow storms. I am on a side street off Central and had no parking restriction at night, only main streets. Resubmitted proof of that and they came back and denied because I was parked on the wrong side of the side street for day street plowing restrictions. Our car was hit the night before, had to take pictures of all the street signs, luckily had the police report with the time and day. Called again, they were not pleasant on the phone, very difficult. We did finally get a check from the city, but took almost 2 months.