THE NUMBER
About 1 in 3 times a car dealer’s AI tried to hand a service caller to a person, the handoff failed: the call went to voicemail, got cut off or sat on hold that never ended. Pied Piper, a company that measures how dealers handle customers, found it by contacting every dealership in the biggest US dealer groups, and it says the dealers’ own reports may show everything working as intended.
3 THINGS HAPPENING RIGHT NOW
TruckSmarter told drivers on a Tuesday that its AI dispatcher would be gone Friday
TruckSmarter built Dispatch so a truck driver could ask for freight in plain words while software agents bid on loads and booked them. On Tuesday, September 1, the company said it had been sold, and an email from the company said the app would shut down “this Friday, September 4.” The company said subscriptions would end that Friday and recent payments would be refunded. The company didn’t say who bought it. FreightWaves wrote that drivers were “getting four days notice on a tool some of them built a workweek around.”
Allianz named its AI after a manager’s old mentor and made it show its sources
Benjamin Blackie wanted Allianz UK’s underwriters to stop losing hours in guidance documents that can run to 600 pages. The tool Allianz built answers an underwriter’s question from those guides, and every answer comes with “a direct link to the specific section of the guidance document used to generate the response,” so anyone can check it in one click. Blackie named it BRIAN, after a colleague who guided him early in his career, “so every underwriter can have what I had when I first started.” Allianz estimates it saved 135 working days of searching between its January 2025 rollout and that September.
Google’s AI invented a $4 pizza deal, and a family restaurant refused to honor it
Customers were calling Stefanina’s in Wentzville, Missouri, about a special it had never run: buy a pizza, get the second for $4. Google’s AI search summary had told them about it, and told some of them a large cost the same as a small. “We’re like, what are you talking about?” said Eva Gannon, whose family owns the restaurant. Angry customers were yelling at the staff, and by August 2025 the restaurant had posted on Facebook that it “will not honor the Google AI specials.” In January 2026 it was still telling customers to contact the restaurant directly. “We can’t, as a small family business, honor a Google AI special,” Gannon told InvestigateTV.
THE DEEP DIVE
Paul Birrell found 400,000 emails he never meant to send
Paul Birrell went looking for a file and found that his business had sent about 400,000 emails in three days. He runs a food and catering delivery service in New Jersey, a soup subscription he started this year and a consulting practice, with about 30 AI agents and a handful of human contractors. An automation he’d set up months earlier was stuck in a loop. “I don’t have 400,000 customers,” he told Forbes.
A second loop, in his text messaging, ran up a bill in a single day before he caught it. Nothing flagged either one. There’s no security team to do it.
So he stopped trying to prevent every mistake and built a way to spot one early. A job now reports his messaging spend every four hours, with an instruction attached at the end. “Put the brakes on it. Stop it,” is how Birrell puts it. Spend jumps when something runs away, so a check every four hours catches a loop the same day, not three days later when he happens to go looking for something else.
“It can see the flood before the dam breaks and get in there and plug it,” he says.
ONE THING TO TRY THIS WEEK
Week 3 of 4: The silence alarm
Most breaks are quiet. A login expires, a tool shuts down or a model gets retired, and the work just stops, with no error and nothing on the bill. The fix is a watcher that tells you when the work stops or runs away, plus a card that shows whose inbox each warning lands in.
Search your email for each of these on its own, going back six months: “action required”, “shutting down”, “retiring”, “expiring” and “expired”. Then look in your spam folder for the same words. Anything about a tool you use is a change someone already tried to tell you about. OpenAI, for one, set a batch of older AI models to switch off on October 23 and says it emails the customers actively using a model before it retires it. If someone else set up your tools, check whose inbox that email went to.
Pick one thing that runs on its own for you. If you built the two agents from last issue, use them. On paper, list everything it needs to work: each account, login, spreadsheet, inbox or service. Next to each, write whose email gets the warning when that thing changes. Any line where the answer isn’t you is a risk. Last line: “I’ll know it worked today because ___.” That’s its receipt, like a new row in the sheet or a sent email in your Sent folder.
On a Mac open Terminal, on Windows open PowerShell, type
claudeand press enter. Paste: “Set up a separate watcher for [name the automation]. Never change the automation itself. On every day it’s meant to run, by [time], check for this receipt: [paste your line]. If it’s missing, or there’s way more of it than usual, send me one line saying so. Every Monday, send me ‘still alive: N receipts this week.’ On the first of each month, take me through this card one line at a time and ask whether each thing still works and still emails me: [paste your card]. Set it to run on its own and tell me when it’s ready.” Connecting the watcher to your inbox or sheet can take one setup step, and Claude will tell you what it needs.Test it once. Ask Claude to run today’s check as if the receipt were missing, and make sure the message reaches you. Then leave it alone. If a Monday note doesn’t arrive, the watcher itself has stopped. That’s why it writes to you even when everything is fine. Put a repeating Monday reminder on your phone that asks, “Did the still-alive note come?”
Stuck? Reply to this email. I’ll help.
WHAT’S COMING
Next issue: if you vanished for two weeks, which of your agents would still be working on day fourteen, and what would someone need to take them over?
Manu