The worst change I ever made to a production environment took months to fully surface, and I'd made it deliberately, carefully, and for good reasons.
Microsoft had renamed the user shell folder from Documents to My Documents, or back the other way depending on which era you're counting from, and the Group Policy that redirected user folders needed updating to reflect the new path. I made the change. It applied cleanly. Spot checks looked fine. New logons picked up the new path, redirection worked, files were where they were supposed to be, and the change moved out of my head and into the pile of things that were done.
The problems started turning up weeks later and didn't look like a Group Policy problem. A user couldn't find a file they were sure they'd saved. Another user's application was writing to a path that no longer existed for anyone else. A third user had two folders with overlapping contents and no clear sense of which was current. Each one looked like a user error or an application quirk in isolation, and each one got handled in isolation, which is the worst possible way to handle a pattern.
The mechanism was that the rename hadn't been clean for every profile. Existing profiles, profiles that had logged on before the change, profiles that had been roamed, profiles that had been touched by older policies still cached somewhere, all behaved slightly differently from the freshly minted ones I'd tested against. Some users were reading from one path and writing to another. The redirection was working exactly as configured. The configuration was correct. The environment underneath it wasn't uniform enough for "correct" to mean the same thing for every user.
What made it take months to surface was that nothing failed loudly. No error dialogs, no event log entries that pointed at the policy, no helpdesk ticket that said "since the Group Policy change". In fact, the helpdesk started doing "Profile Resets" which caused even more harm and user data loss.
The symptoms were all downstream and all human: missing files, confusion, duplicated work, the slow erosion of trust in the file server. By the time I traced it back to the change I'd made, the incident had stopped being a Group Policy problem and started being a data hygiene problem across dozens of profiles, which is a much harder thing to fix than the original change would have been to roll back.
The lesson I took from it, and the reason I still think about it nearly 15 years later, is that a change being technically correct is not the same as a change being safe in the environment you're applying it to. The test environment was uniform. Production wasn't. Nothing in my process at the time was designed to find that difference before users did.
The technical trigger is always recent. The cause is usually older than the trigger, and sometimes the cause is you.