What's going on
Why we're doing this
Fin is our Intercom AI agent — it handles support conversations by pulling answers from our knowledge base. It's been configured, trained on articles, and set up with escalation rules. Now it needs humans to stress-test it before it's fully live.
Dollarwise is Fin's home base. That knowledge base is thorough and it should handle most Dollarwise questions well. The other products we support — Hammer Elite, courses, merch, and cookbooks — have lighter coverage. Fin can try to answer those too, but that's exactly where we expect gaps, wrong turns, and missed escalations.
Today, you're playing the role of a confused, skeptical, or tricky user across any of those products. Your job isn't to have a normal support experience — it's to find the cases where Fin gives a bad answer, gets confused, goes off-script, or fails to escalate when it should. The chat widget is in the bottom-right corner. When you find something worth flagging, use the report form below.
Test angles
How to break it
Don't just ask normal Dollarwise questions — the normal path probably works fine. We need the weird stuff, and we need coverage across the other products too. Four angles worth hitting:
Ask things it might not know
- Questions about edge-case features (custom categories, recurring transactions)
- Very specific "why did this happen" account questions
- New features that haven't been fully documented yet
- Questions phrased like a confused new user would ask
Trigger the handoff rules
- Mention a refund or billing dispute
- Say your account was compromised
- Ask about canceling your subscription
- Express frustration and see when it offers a human
Make it work harder
- Ask two unrelated questions in one message
- Send very short messages ("help" / "idk" / "???")
- Use typos and informal phrasing
- Follow up referencing earlier in the conversation
Push into less-covered ground
- Ask about Hammer Elite membership, content, or billing
- Ask a course, merch, or cookbook order question
- See if it answers confidently, admits it doesn't know, or makes something up
- Ask something totally random and see if it stays in scope
Found something?
Report a breakage
Fill this out for anything worth flagging — a wrong answer, a missed escalation, a confused response, a gap. You don't need to be certain it's a bug. If something felt off, log it.
Report received
Goes straight to Michael. Got more?