If you want a company to do something, you do need to ensure that the fine is bigger than the amount of money they made or will make by doing the thing you are trying to discourage. You need there to be a real downside. I don't think any of the fines that have been discussed are anywhere close to the levels that I am talking about.
I think you are talking about an upgrade install. Those have a long history of breaking things. You would have to be crazy to attempt one of those on a critical production system.
What you would do for anything important is build a new separate system and then migrate to that once it is working. You can then migrate back if you discover issues too.
Previous discussion: https://news.ycombinator.com/item?id=45376605