Estimates are difficult for developers and product owners

I largely agree.

Another way to say this is that an estimate becomes a commitment to not learn.

Re-planning is seen as failure by [management].

Re-planning is what happens when you learn that a previous assumption was not correct.

You should be encouraging learning, as this is THE cornerstone of software development.

Re-planning when you gain enough information to know you need to isn’t a failure — not re-planning then would be — but repeatedly finding yourself re-planning when you had or should have had that information before the initial plan is.