Netflix also famously went this route, allowing rampant password sharing and then deciding "Hey, we want to get paid!" On one hand I don't have a problem with companies wanting to get paid for what they produce, but on the other, given that allowing the piracy is a deliberate decision they made from the get-go, I don't have a problem telling them to get bent once they decide "Time for profits! Enshittification it is..."
That said, this strategy is surefire when it comes to consumer products like Windows. Consumers will stick with what thye are comfortable with. The Network Effect. It's a huge gamble for professional tools like Adobe, and they are somewhat lucky there wasn't a timeline where GIMP un-GIMPED itself, nor where Krita and other modern competitors didn't get adopted faster. There's money at stake, so professionals can and will learn new tools if the tools bite them.
(Lest you think I am joking, have a look at the 'MoviePass economy.')
It’s like when someone offers to sell you a product weighed in grams, you can’t just say ‘ah yes, the drug dealer measurement system’ and dismiss their business out of hand.
Because I don’t think the moral issue people have with drug dealers is that they take a deliberately easy going attitude to theft of their merchandise and allow others to profit from selling it to a territory, only to later on increase their prices.
See also how 'picking the low hanging fruit first' would get you fired from any picking gig: the fruit higher up the plant tends to ripen first. So that's what you pick first.
There's lots of other funny (business) metaphors going wrong.
See also how a 'quantum leap' is the smallest possible change possible, not something big and amazing.