I tried this with an app. They offered 2% off after a month of data collection. I called and turns out my insurance was already so “low” that 2% is the most it would have ever offered. I dunno about elsewhere but in Canada, insurance is like tech job salaries, the only real way to get the best deal is to change providers every few years.
I have a hunch that the risk is the longer they keep you the more likely to have an accident they have to pay out. So if you are a good customer, no claims for 3 years your engagement with them has been very profitable. If they keep you for another year and you have an claim then that engagement is unprofitable. Just a hunch as insurance math is complicated.