# Chapter 11. When the Worker Goes Wrong (/managing-ai-workers/when-the-worker-goes-wrong/overview)

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title: "Chapter 11. When the Worker Goes Wrong"
description: "How to stop a failing AI Worker, read its task record, check that a run really worked, find which of five causes a failure comes from, and fix it so the fix lasts, on Claude or ChatGPT."
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## The point

Chapters 5 to 10 taught you to manage an AI Worker, an AI that holds a role at work. You learned to brief it, review its work, set its limits, give it knowledge, schedule it and govern it. All of this lowers the chance of a bad result. It does not remove that chance. This chapter is about the day a result is wrong anyway.

Troubleshooting means finding where a failure lives, which is the place it comes from. Then you fix that place and nothing else. The chapter answers seven questions:

| Question | Concept | You can then |
| --- | --- | --- |
| What did the worker actually do? | 11.1 | Stop it, read its record, and check what changed |
| Did it work, or did it only run? | 11.2 | Give every job a **success signal** |
| Where does this failure live? | 11.3 | Run the five checks, cheapest first |
| Did it reach a usage limit? | 11.4 | Read usage and limits on Claude and on ChatGPT |
| What should I change? | 11.5 | Fix the brief, the inputs or the permissions, then test the fix |
| How do I stop fixing it by hand? | 11.6 | Move fixes into the worker's setup, and measure them |
| What do Claude and ChatGPT show today? | 11.7 | Find each AI vendor's step list, scheduled runs, pause reasons and usage pages |

This chapter deepens **Discernment**, one of the 4Ds of AI fluency: Delegation, Description, Discernment and Diligence.

## Why it matters

Brightline Wholesale Supply is the book's example company. In January 2027, its AP Worker had run two recurring jobs on its own since November 9 (Chapter 9). AP means accounts payable, the bills a company owes, and the AP Worker is the AI Worker that handles them. Its two jobs were the Thursday pre-run note and a duplicate check on each invoice email. Maria, the office manager, ran the worker day to day. Dave Kowalski, the controller, approved what it worked on. Jordan Ellis, the clerk hired to help at year-end, had stayed on for the January close of the accounts.

> **Two terms used below.** A *register* is the list of every invoice the company owes, with its due date and status. A *remittance notice* is the note that tells a vendor which invoices a payment covers.

Then, in one week, four things went wrong.

**Monday, January 11.** Maria spent the afternoon on a large year-end task, matching twelve months of vendor statements against the register. She worked from her seat, her own account in the company's AI workspace. **Tuesday, January 12,** nine invoice emails arrived. The duplicate check runs on each invoice email, but this time it checked none of them. It posts a message only when it finds a duplicate, so its silence looked like good news. One of the nine was Kenton Box & Crate's invoice 7781, sent again as 7781-R for $4,812.50. It was entered and scheduled for the next payment run.

**Wednesday, January 13.** Jordan asked the worker to "reply to these three vendors about their short payments." A short payment is when Brightline pays a vendor less than the invoice says. All three drafts said Brightline used the same terms with every vendor: "2 percent 10, net 30." That means a 2 percent discount for paying within 10 days, and otherwise the full amount within 30 days. They also said the amount Brightline took off was the early-payment discount. But Stonebridge Carton's terms are net 45, which means pay within 45 days, with no discount. Brightline had paid it less because of a credit for damaged cartons. Maria noticed the mistake in her review.

**Thursday, January 14, 7 a.m.** The pre-run note, the summary Dave reads before he approves each Friday's payment run, said "No invoices due this week." Maria saw a short note in the usual layout and forwarded it to Dave. He was pleased. In fact, 31 invoices, worth $86,240.15, were due. After the January 8 payment run, Maria had closed the 2026 register and started "AP Register 2027." The old file was closed and fully paid, but it was still called "AP Register," the name the job looked for. The job checked that name, not the date of the file's last entry. So the January 15 run paid none of the 31 invoices. They were paid a week late, except 7781-R, which could still be stopped.

**Friday, January 15.** Five replies to vendors said "Attached is the remittance notice." Nothing was attached. On January 4, the IT team had reset passwords, and the worker's link to the shared drive had stopped working. Its record said "access denied" at step 2. It continued anyway, and Maria sent all five without opening an attachment.

Dave read about all four on Friday afternoon. "Switch to the most expensive model," he said, "and Maria, rewrite every brief from scratch." A stronger model would have fixed none of the four. New briefs would have fixed Jordan's replies, and only part of the other three. Rewriting every brief would also have meant losing every part that already worked. This chapter shows how to find the place before changing anything.
