I've had Progressive for 2 years. It was a relationship that started off well, but only went down hill. When it started, it was a nice low rate compared to other companies. I paid the 6 months in advance to get the discount. Then I switched to the month to month and discovered I could get text alerts when my bill was ready. I was very pleased, except after 6 months they stopped and I was unaware when my bill was ready and missed payment. It was extremely stressful being unaware when the bill was ready, although I knew it was usually the 20th, it would have been nice to continue to receive the reminders. Also, frequently parts of the website just would not load, making it very difficult to pay online. So after another 6 months I thought I should just pay the next 6 months in advance again so I wouldn't have to try to remember every month or rely on the availability of the website. I went online and selected to pay for my last month and the next 6 months, entered my credit card information, and clicked through. I received no indication that anything went wrong.
Today, a month later, I have received an email stating that my policy has been canceled and that I still owe them for the last month. I am extremely dissatisfied that I was not warned that my policy was going to be canceled. It is uncomprehendingly frustrating to have the money to pay a company but have to go over hurdles to get them the payment. I checked my bank statement and no money was charged even though I ended the transaction without any issues. The insurance is constantly going up even though I have only had one fender bender (a decal on the front of my truck hit the work box attached to some other guys work truck) and was told it would not increase my rate. It is just starting to make me feel rather scammed.
I highly recommend you DO NOT use Progressive. And if you decide to for your first year, shop around your second because other companies will give you a larger discount for having it. Unless of course, Progressive's ineptitude results in a lap in coverage.