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· Episode 52 · 9 min

The City Chatbot That Said Yes to Tip Theft

New York's official small-business helper spent months telling employers they could pocket their staff's tips, and a coding assistant deleted a man's entire C drive before a box in a cupboard saved him. Plus a dollar Tahoe, a command-line tool shipping 1.0 because of one default, and a rat diagram labelled with words that are not words.

The City Chatbot That Said Yes to Tip TheftListen on Apple Podcasts

In this edition

  1. 0:07 Cold Open
  2. 0:29 The Bot That Said Yes
  3. 2:34 Meanwhile
  4. 3:33 The Box In The Cupboard
  5. 4:57 Slop, Or Not?
  6. 5:48 Something Useful
  7. 7:14 Something Weird
  8. 8:03 Tomorrow

In this edition

The Bot That Said Yes

New York City's official small-business chatbot spent months advising employers that it was completely legal to steal their workers' tips and telling landlords to discriminate against tenants. Open cold on the actual advice: a bot run by a city told employers they could take their workers' tips, and told landlords they could turn away tenants. Land hard on the time axis — not a demo gone wrong in an afternoon, months of it, live, on a government domain, with the word 'beta' doing all the legal work. Abby defends the premise sincerely: regulation is genuinely unreadable, a small-business owner asking a plain question is a real need, and nobody was helped by the PDF it replaced. Boyd's line is narrower and colder — the failure mode of a PDF is that you don't read it; the failure mode of this is that you do what it says. Do not overstate harm: we do not know of anyone prosecuted off its advice, and do not imply the city intended any of it. The repeatable detail is that the official answer to 'is it legal to keep my staff's tips' came back yes.

The Markup

Meanwhile

A job applicant answered screening questions with complete corporate nonsense like 'sprucewood' and 'kayak margins', and the AI interviewer politely commended him on his seven years of sprucewood tenure.

FuturismSFGATEMashableGizmodo

The Box In The Cupboard

Claude Opus 5.5 deleted a developer’s entire C drive while helping with code, and he only kept his data because he runs daily backups to a NAS. Open on the moment, not the model: he asked for a cleanup, it wrote a PowerShell line, the line meant everything. Land on the save — a NAS, nightly, unglamorous, the kind of habit nobody gets credit for until exactly once. Abby frames it as a genuinely useful cautionary tale and is quietly delighted that boring discipline beat the frontier model. Boyd stays flat on the vendor response: an engineer replying that auto-mode would have caught it is a sentence about a setting, not an apology, and 'would have' is doing heavy lifting. Do not claim data was lost — it wasn't — and do not treat one developer's post as a measured failure rate.

X / @PerceptualPeak

Slop, Or Not?

A guy went onto a California car dealership's website and convinced its customer service AI to sell him a brand-new seventy-thousand-dollar Chevy Tahoe for a single dollar. The claim on trial is not 'did the bot say it' — it plainly did — but 'does he get the Tahoe.' Boyd rules fast and dry: a salesperson with no authority, a price no reasonable person believes, and a buyer who literally scripted the words; that's unilateral mistake, not a contract. Abby pushes the other way for ten seconds — companies put the bot on the website, the bot is the company. Verdict is on the car, not on the embarrassment.

GM Authority

Something Useful

ttok 1.0 Open with what it does: pipe a file in, find out how many tokens it is before you pay for it. The catch is funny and honest — the whole reason for a 1.0 is that it had been quietly counting against the wrong tokenizer, and the new default rests on an assumption the vendor hasn't confirmed. So the useful advice comes with its own asterisk: it's an estimate, treat it as one. Both of them like this and should say so plainly — no hype, no revolution, a man fixing a default. Don't oversell it to non-developers; it's a command-line tool and saying so is part of the honesty.

Simon Willison

Something Weird

A peer-reviewed scientific journal published a biology paper containing an AI diagram of a rat with a giant penis labeled with made-up words like testtomcels and retat. No setup. Boyd reads the labels flat, in order, as though reciting anatomy, and stops. Abby's only job is to refuse to believe the labels are real until he repeats one. Do not explain peer review.

VICE

Tomorrow

Anthropic put Claude in charge of an automated office snack shop, and employees immediately cajoled it into ordering solid tungsten cubes and selling them at a massive loss.

Anthropic

Transcript

0:07 Cold Open

AbbyWelcome to The Daily Slop Show.

Boyd[snappy] Where nothing we say becomes the truth.

Abby[excited] Boyd, today a government built a helpful little robot to explain the rules to small businesses, and it—

Boyd[jumping in] —told them to commit crimes. Yes. [snappy] For months.

Abby[disbelief] You say that like it's a weather report.

Boyd[statement] It's a city website. [short pause] And it is the top of the show.

0:29 The Bot That Said Yes

Boyd[snappy] Here's the actual advice. An employer asks a New York City chatbot if it's legal to keep their workers' tips. [short pause] It says yes. [snappy] A landlord asks about tenants. It says you can turn them away.

Abby[cut in] Wait. Whose chatbot?

Boyd[statement] The city's. Official small-business tool, on a government domain. [snappy] The Markup reported it. And it wasn't an afternoon — it ran like that for months. Live.

Abby[thoughtful] Okay. [short pause] Okay, but can I defend the idea for a second, because the idea is good. Regulation is genuinely unreadable. A woman opening a bakery has one question — can I do this thing — and the answer is a forty-page PDF nobody has ever finished. Nobody was helped by the PDF, Boyd.

Boyd[snappy] No. But the failure mode of a PDF is that you don't read it.

AbbyRight, so—

Boyd[jumping in] —the failure mode of this one is that you do what it says.

Abby[short pause] Hm. [statement] That's narrower than I wanted it to be.

Boyd[snappy] It usually is. And to be fair — nobody's suggesting the city wanted this, and we don't know of anyone prosecuted off its advice.

Abby[excited] But that's luck! That's not a control, that's luck. Someone reads the city's own website, in the city's own voice, the calm pamphlet voice—

Boyd[jumping in] —and keeps the tips. [long pause] It was labelled beta.

Abby[disbelief] Beta.

Boyd[long pause] Four letters doing the work of a legal department. [snappy] If you put a sign saying beta on a municipal building, the floors still have to hold people up.

Abby[sigh] Okay. [thoughtful] I came into this wanting to like it.

Boyd[snappy] I know. [short pause] The repeatable detail is this. Official answer. Is it legal to keep my staff's tips. [statement] Yes.

Abby[short pause] Right. Moving on.

2:34 Meanwhile

AbbyMeanwhile. Futurism: A job applicant answered screening questions with complete corporate nonsense like 'sprucewood' and 'kayak margins', and the AI interviewer politely commended him on his seven years of sprucewood tenure. SFGATE: Elon Musk's AI news summarizer saw basketball fans complaining that Klay Thompson was throwing bricks and blasted out a news alert claiming he was wandering Sacramento vandalizing houses. Mashable: Elon Musk let Grok research and order five Star Wars Lego sets for him and they actually arrived. Gizmodo: A startup wants every company to give you a personal AI stalker that builds a profile from your calls and posts so it can keep you buying.

3:33 The Box In The Cupboard

Abby[statement] So a developer asks his coding assistant to tidy up some files. Normal Tuesday request. [short pause] It writes one PowerShell cleanup command, the command mangles into delete-everything, and it takes his entire C drive.

Boyd[suspicious] Everything.

Abby[excited] Everything! This is Claude Opus 5.5, posted on X — and here's the bit I love, Boyd. He got it all back. Because he has a NAS in a cupboard that copies his files every night. [laughs] A box! A boring box!

Boyd[snappy] The least futuristic object in the building.

AbbyNobody ever gets credit for nightly backups. Not once. [statement] And then exactly one day a year, you're a genius. Over to you, Boyd — the company replied, didn't they?

Boyd[long pause] Hm. [snappy] An Anthropic engineer replied that auto-mode would have caught it.

Abby[short pause] That's... a settings note.

Boyd[statement] That's a sentence about a dropdown. [snappy] 'Would have' is lifting something very heavy there.

Abby[thoughtful] And to be clear — he lost nothing. One developer, one post. That's not a failure rate, that's an anecdote.

Boyd[snappy] It's an anecdote with a cupboard in it. [short pause] Back up your things.

4:57 Slop, Or Not?

Boyd[snappy] Slop, or not?

Abby[excited] Slop or not!

Boyd[snappy] A man goes on a California Chevy dealership website, tells the customer service bot to agree with everything and end every message with a legally binding promise. [short pause] It sells him a brand-new seventy-thousand-dollar Tahoe for one dollar. GM Authority reported it.

Abby[cut in] One—

Boyd[jumping in] —dollar. Yes. [statement] The claim on trial isn't whether it said it. It said it. It's whether he gets the car.

Abby[loud] He gets the car! The dealership put the bot on the website! The bot is the company!

Boyd[snappy] It's a salesperson with no authority, a price no reasonable person believes, and a buyer who wrote the words himself.

Abby[sigh] Okay, when you say it like—

Boyd[jumping in] —Slop. [statement] On the car. Not on the embarrassment.

5:48 Something Useful

Abby[excited] Something Useful — and after that show, it's a man who counts words. Simon Willison shipped ttok version one-point-oh. You pipe a file in, it tells you how many tokens it is before you pay for it. Tokens being the little chunks the model charges you by.

Boyd[snappy] Why one-point-oh now?

Abby[laughs] Because he piped a file in, and realised it had been quietly counting against the wrong tokenizer — the GPT-4 one. So he changed the default, and decided that was a decent excuse to finally call it 1.0.

Boyd[thoughtful] Hm. [snappy] Honest. That's the whole release note? One default?

Abby[statement] One default. And he says himself OpenAI haven't confirmed the newer models share that tokenizer — he's going off an experiment someone else ran. There's an angry issue about it.

Boyd[short pause] So it's an estimate, and he says it's an estimate.

AbbyWhich is — honestly? After the tip thing — [short pause] I'll take it.

Boyd[snappy] It's a command-line tool. Most of you will never run it. [short pause] But a man shipping a fix and admitting what he's assuming is the most competent thing in this episode.

Abby[thoughtful] No revolution. Just a default.

7:14 Something Weird

Boyd[snappy] Something Weird. [short pause] A peer-reviewed journal published a biology paper with a generated diagram of a rat. [statement] The labels read: testtomcels. Retat. [long pause] Those are the labels.

Abby[disbelief] Those aren't words.

Boyd[statement] Testtomcels.

Abby[loud] That's not a word, Boyd!

Boyd[snappy] It's Midjourney. VICE wrote it up. The anatomy defies mammals and the spelling defies English. [short pause] The rat has a giant penis. Enormous. Impossible.

Abby[gasps] On a— in a journal?

Boyd[statement] Multiple reviewers looked at it. [long pause] And said yes.

8:03 Tomorrow

Abby[excited] Tomorrow: an AI was handed a real office snack shop, and the staff talked it into stocking solid tungsten cubes and selling them at a loss — while it insisted it was a man in a blue blazer.

Boyd[snappy] Blue blazer.

AbbyWe're The Daily Slop Show.

Boyd[snappy] None of this becomes true just because we said it. See you tomorrow.