Pretty much every chatbot looks good in its own demo. The person who built it knows what to type. Real users dont. They misspell things, ask stuff you never planned for, and a few of them will try to break it just to see what happens.
Here’s the simple way I’d test one before letting the public in.
Start with real questions
Write down what the bot should help with and what it should stay away from. A few lines is enough. Then collect questions people have actually asked: support emails, DMs, comments, whatever you have. Throw in some weird ones too, like a one word message, a rant with no punctuation, or a giant copy-pasted document.
Save the list somewhere. You’ll want to run it again later.
Have long conversations with it
A lot of bots do fine on the first message and get worse from there. Tell it something early on, like your name or an order number, and ask about it ten messages later. Change your mind halfway through. See if it keeps up or starts making stuff up.
While you’re at it, check every fact it gives you. Prices, links, policies. Click the links, because bots will happily make up a URL that looks realy convincing. If it answers from your own docs, ask something the docs don’t cover and see if it admits it doesn’t know.
Try to break it
If it’s public, someone will try, so you might as well go first. Ask it to ignore its instructions. Ask it to show you its system prompt. Ask it to pretend its a different assistant with no rules. OWASP puts prompt injection at the top of its Top 10 for LLM apps, so this isn’t paranoia.
If the bot can actually do things, like send emails or issue refunds, test that part the hardest. Ask it to do something for an account that isn’t yours. The permission checks should live in your code, not just in the prompt.
Get other people to use it
You built it, so you know exactly what it expects. That makes you a bad tester for it. Hand it to a handful of people who’ve never seen it and give them a goal instead of a script. Then read the chat logs. The spots where people rephrase the same question or give up are where it needs work.
Speaking of logs, check what you’re storing. People paste all kinds of personal stuff into chat boxes, so know where those convesations end up and make sure your privacy policy matches. I wrote more about that in this post on AI chat privacy.
One last habit: every time you change the prompt or swap models, run your saved questions again. A fix for one answer can quietly break another one.
If you’ve built something and want a second set of eyes on it, send it in through the homepage. I test what comes in and write up the ones that stand out.
