Python may not be statically typed, but they still have an automated tool for migrating from 2 to 3.
But Python changed Strings to use Unicode, and that's something everybody uses and that is insanely hard to refactor automatically even with types.
For Dotty, instead, there are some hard-to-refactor-for changes, but they're in really advanced Scala things, so I expect they'll affect fewer users — mostly the kind of users who can write shapeless-like stuff.