OSWEGO, NEW YORK -- When I was 18 I had progressive insurance. They had failed to send me my auto insurance bill. After about a month (In 18 year old terms). I called them up and asked where my bill was. They told me that I was a month and half over due. They then told me (this is through their number not through a third party), that my insurance was cancelled and this put me into a risk pool so I had to pay a higher rate, but they would retroactive me back to my cancellation date. I told them no. A few days later I got a letter in the mail from the DMV, stating that Progressive had informed them I had no insurance.
Funny how the letter was dated the day I called them. So I had to put my car off the road or pay a fine. This also happened to two other people I had met in my travels.