Ever launch a product update that users actually hated you for fixing?

We had this weird situation where power users got so attached to an old workaround that when we built a real, automated version to fix it, people got annoyed instead of happy. Turns out, when someone builds a routine around a specific glitch or manual export, taking it away feels like you're breaking their daily workflow, even if the new way saves time. We had to realize that "better" doesn't always feel better if it shows up without warning. How do you handle shipping big updates to core features without pissing off the people who use your product every day?