Real Agent Cases

Get a 0.75% to 12.75% unemployment insurance rate jump fixed retroactively with ChatGPT filing the missing wage report

Posted
by mattmaroon (Hacker News)
Last checked
Method:
How we verify

Evidence: Described by posterThe person describes what happened in words, without screenshots or video.

Outcome

mattmaroon runs a seasonal business and noticed their state unemployment insurance rate had jumped from 0.75% to 12.75%. Instead of hours on the state website and on hold, they asked ChatGPT what had happened. It worked out that they were being charged a penalty rate because their new payroll provider doesn't file wage reports for the one quarter with no wages, and without a report the business counted as delinquent. ChatGPT filed the correct wage report and went to the support site to request a retroactive rewrite, which was granted, saving many thousands of dollars without hitting the 5-hour usage limit.

Agent

ChatGPT

Prompt Recreated prompt

The source didn't share its exact prompt, so we wrote this from what it describes.

Before you start, ask me 1–3 short questions about anything important that's missing below. Keep them quick. Then do the task, checking in with me at the key points.

Goal: Find out why a business tax rate suddenly jumped and help me get it corrected.

What I can give you (ask for whatever's missing):
- The notice or rate change, with dates: [ATTACH / DETAILS]
- State and type of tax or insurance: [DETAILS]
- Anything that changed recently (payroll provider, staff, seasons): [DETAILS]

You're not my accountant or financial adviser. Show your working, label estimates as estimates, and tell me which points a professional or the official source should confirm.

Rules:
- Check the state agency's official rules for what triggers a penalty or higher rate.
- Compare those triggers with what changed for me and tell me the most likely cause.
- List the filings or forms needed to fix it, with deadlines.
- Draft any request for a correction or retroactive change, and show me before anything is filed or sent.
- If a site asks me to sign in, pause and let me do it myself (including any CAPTCHA or two-step code); never guess or store passwords.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.

Output: The likely cause, the fix, and draft filings or requests.

You'll know it worked when: the agency corrects the rate and any overcharge.

Try this in:

This prompt has blanks to fill in, like [ATTACH / DETAILS]. We'll copy it instead of filling it in, so you can edit it before you send.

Opens in a new tab. We don't see what you send.

These links are only a shortcut. We're not affiliated with OpenAI, Google or xAI, and your results may not match the source.

Optional stronger version

Our rewrite with extra checks. The poster didn't test it.

Before you start, ask me 1–3 short questions about anything important that's missing below. Keep them quick. Then do the task, checking in with me at the key points.

Goal: Find out why a business tax rate suddenly jumped and help me get it corrected.

What I can give you (ask for whatever's missing):
- The notice or rate change, with dates: [ATTACH / DETAILS]
- State and type of tax or insurance: [DETAILS]
- Anything that changed recently (payroll provider, staff, seasons): [DETAILS]

You're not my accountant or financial adviser. Show your working, label estimates as estimates, and tell me which points a professional or the official source should confirm.

Rules:
- Check the state agency's official rules for what triggers a penalty or higher rate.
- Compare those triggers with what changed for me and tell me the most likely cause.
- List the filings or forms needed to fix it, with deadlines.
- Draft any request for a correction or retroactive change, and show me before anything is filed or sent.
- If a site asks me to sign in, pause and let me do it myself (including any CAPTCHA or two-step code); never guess or store passwords.
- Ask for my OK before you pay, book, send, submit or cancel anything.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.
- Tell me how to stop it happening again, for example a zero-wage report for quiet quarters.

Output: The likely cause, the fix, and draft filings or requests.

You'll know it worked when: the agency corrects the rate and any overcharge.

Before you finish: re-read my goal and constraints, check your answer against each one, and list anything you assumed or couldn't confirm.

Source

https://news.ycombinator.com/item?id=49467734

  • badlibrarian runs a business and sometimes buys things on Amazon. At tax time they used to search for the big business items and categorise them in QuickBooks Online until they gave up, using a janky browser plugin and two monitors full of Excel windows. Now Claude does it and doesn't give up, despite QuickBooks being slow. It will even click 19 times to split a transaction because they'd put a router and shampoo in the same Amazon cart one night in February 2025.

    Claude · Ops · Source date:

  • Sridhar Katakam used Claude Cowork to go through the statements and transactions from several bank accounts, Stripe, PayPal and Wise and prepare business expense and income spreadsheets. Their accountant reviewed them and said they were good enough that Katakam no longer needed the accountant's services for BAS and could file it themselves, a saving of about $530 AUD per quarter. The accountant also suggested having Claude do the same for the whole year, and said the fee for filing the income tax return would come down.

    Claude Cowork · Ops · Source date:

  • Ask Claude whether to convert an LLC to an S Corp, and miss that NYC taxes make it cost moreRecreated promptEvidence: Described by posterFailureBeginner-friendly

    mikeocool asked Claude about converting their LLC to an S Corp. Claude said it was a great idea and estimated how much they would save in taxes. Their accountant said it would actually cost more, because of how New York City taxes S Corps. They hadn't told Claude they lived in NYC, because it didn't occur to them that it mattered. Their takeaway: tax questions are full of details like this, often subtler than where you live.

    Claude · Ops · Source date: