Knowing when to stop prompting
Some loops don't converge. Here's how to spot one early.
The single most expensive habit in vibe coding is continuing to prompt a conversation that has stopped improving. It feels like progress — messages are being sent, code is coming back — and the code is getting steadily worse.
The three-strike rule
If the same problem survives three attempts, stop. Do not send a fourth "that didn't work either". Three failures means the model does not have what it needs, and more attempts will produce more variations of the same misunderstanding.
What to do instead
Change the context, not the wording. The fix is almost never a better phrasing of the same request. It is more information: the actual error text, the whole file rather than a fragment, the versions you are on, what you already tried and what happened.
Start a fresh chat. Long threads carry every wrong turn. The model has read its own bad guesses and will stay near them. Open a new one and describe the problem as if to someone who has never seen it — which is often when you spot the thing you never mentioned.
Get smaller. If a feature will not come out right, ask for one piece of it. Just the function. Just the query. Assemble it yourself.
Ask it to disagree with you.
We've tried three times and it still <what happens>. I think the problem is <your theory>. Assume my theory is wrong. What else could cause this? List the three most likely alternatives and the fastest way to rule each one out. Also: what have I not told you that you'd need to know?
That last line is the most valuable question in this entire site. Ask it whenever you're stuck.
The other kind of stopping
There is a second stopping point that matters more: when the thing works.
A working tool with an ugly button is finished. A working tool you are still "improving" at midnight is a working tool you are risking. When your project does the thing in your one sentence, commit it, put it online, and let a real person use it before you write another line.
Nearly everything you would polish in that next hour is something you would have removed after watching one person use it for two minutes.