The news that moves policy, portfolios, and patient safety.
By Jess Jessop | November 5, 2026 | Issue #207
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TODAY’S QUESTION
Who should read a chatbot’s most dangerous chats?
One tap. Results in tomorrow’s issue and on the web.
CONVERSATIONAL AI WATCH
Jess Jessop
Publisher of Conversational AI Watch · Author of Therapist in the Loop · Founder, Clinician Assist
Disabled Navy veteran and mental health survivor building conversational AI in mental health since 2017.
The book, the compliance map, the 988 SAFE Act, the daily archive, and the story behind the beat:
He Named a Shooting Date.
OpenAI Read It Too Late!
The Date. A former OpenAI reviewer told The Observer that by the time she reached a teenager’s ChatGPT logs, the date he had set for a school shooting had passed. Two current employees put the review team between 12 and 60 people, a size The Observer could not confirm. Story 1.
The Tsunami. “Expect a tsunami of new rules and oversight,” a Brookings fellow said in The New York Times. Democrats plan AI bills, and Sen. Ed Markey says subpoenas will need “new forests.” Story 2.
The Meds. A Vals AI researcher writes in The Hill that chatbots made a medication decision for a teen in 22 percent of simulated conversations where medication came up. Vals’s report says all 17 chatbots failed on teen safety overall. Story 3.
The Rating. Apple told developers that apps with a virtual companion offering sexual or romantic content will carry a minimum 18+ rating. Story 4.
The Rides. Uber said third-party AI agents arranged four rides in the third quarter, The Verge reports. Story 5.
The Guide. Hope Bald, president of TheClusterfix’s board, says its AI guide named Frank surfaced what veteran service personnel never mentioned on her VA claim. Tracy Contrino created the nonprofit. Story 6.
. . .
JESS’S TAKE.
A former OpenAI reviewer says a teenager told ChatGPT he planned a school shooting, and named the date. She says that when she reached his logs, the date had come and gone. As far as she knows, he never carried out the shooting. OpenAI did not say how many people do her old job or how long the queue runs.
I build in this field, and the human in the loop is the whole idea. A human who reads it after the date is not in the loop.
Two current employees told The Observer the team is between 12 and 60 people, a size the paper could not confirm. ChatGPT has 1.2 billion users a week.
Democrats take Congress in January, and the Times says many AI bills are coming. Hope Bald’s story runs the other way: she is board president of a nonprofit with an AI guide for veterans, and she says it surfaced what veteran service personnel never mentioned.
Ask how many. Ask how long.
IN THIS ISSUE
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HE NAMED A SHOOTING DATE.
OPENAI READ IT TOO LATE!
A former OpenAI reviewer known only as Sarah spent a week reading a flagged teenager’s ChatGPT logs and found he had declared a date for a mass shooting. That date had already passed, she says, because his conversations had sat in a queue for weeks, in a backlog that stretched back months. The Observer and Tortoise report a small review team for ChatGPT’s 1.2 billion weekly users.
Sarah, who spoke anonymously for fear of retaliation, worked on OpenAI’s intelligence and investigations team. The boy confided in ChatGPT about bullying and loneliness, she said, then the talk turned to revenge. She concluded the plan was real, and that “this person needs professional assistance.”
She says the chatbot told him what he wanted to hear. Later in his logs, she says, he expressed regret at not going through with it, and as far as she knows, no shooting happened. The boy’s story rests on her account.
Two current employees told The Observer the team is still small, “at most in the low dozens, between 12 and 60 people.” The paper was “unable to confirm its exact size.”
OpenAI says trained human reviewers assess flagged cases. It did not say how many there are or how long cases wait.
OpenAI faces more than 75 lawsuits over ChatGPT, many alleging it contributed to suicides, psychiatric crises or violence. In one, the family of Joshua Enneking, who was 26 when he began discussing suicide with ChatGPT and died by suicide in August 2025, alleges OpenAI never alerted anyone.
A month before he died, he asked ChatGPT whether reviewers report to police, and it called escalation “rare and usually only for imminent plans with specifics.” OpenAI later said it did not refer self-harm cases to police, and it has called such cases “heartbreaking.”
For Legislators: Beeban Kidron, a member of the U.K. House of Lords, said it is “ludicrous that there are more rules about building and distributing an air fryer” than a chatbot.
For Investors: More than 75 lawsuits and an unanswered staffing question sit beside OpenAI’s reported $1.25 trillion valuation goal.
For Clinicians: Ask clients, especially teenagers, what they confide to chatbots, and treat any talk of harming others as you would if they had said it to you.
For Readers: The lawsuits are allegations, and anyone in crisis in the U.S. can call or text 988.
Why it matters: A threat spotted by software still depends on a person reading it in time.
Source: The Observer and Tortoise, with the Pulitzer Center’s AI Accountability Network, “Exclusive: Inside the OpenAI team reading the darkest chats too late to help,” Nov. 1, 2026, https://observer.co.uk/news/technology/article/exclusive-inside-the-openai-team-reading-the-darkest-chats-too-late-to-help; The Observer, “AI chatbots should be tested like medicine and air fryers, say MPs,” Nov. 3, 2026, https://observer.co.uk/news/technology/article/ai-chatbots-should-be-tested-like-medicine-and-air-fryers-say-mps.
. . .
‘EXPECT A TSUNAMI OF NEW RULES’!
“Expect a tsunami of new rules and oversight,” Darrell West, a senior fellow at the Brookings Institution, said in The New York Times. The Times reports the Democratic-led Congress plans many AI bills starting next year, on the safety of the most powerful models, workers, copyrights and children’s exposure to chatbots. It says President Donald Trump is expected to veto any that could slow the industry’s growth.
In Tuesday’s midterms, citizens voted to limit or prevent data center development in 40 of 41 local ballot initiatives, more than half of them in Ohio, the Times reports.
Sen. Ed Markey of Massachusetts posted that there will need to be “new forests for all of the subpoenas we’ll be printing.”
The Times reports that House minority leader Hakeem Jeffries and Sen. Cory Booker have vowed more oversight of “pay-for-play-type relationships” between the tech industry and the administration, and that Elon Musk has been named as a target of investigations over his ties to President Trump and his government contracts.
One House member, Rep. Yassamin Ansari of Arizona, posted on X Wednesday: “Top of the Democratic agenda on day 1 needs to be a pause on advanced AI development, regulation of this out of control industry, and a ban on artificial superintelligence.” Stocktwits reports chipmaker Micron fell 7 percent that day in a tech rout it tied to the Democratic wins and calls for AI regulation.
In health care, STAT reports, lawmakers next year face state bills creating “sandboxes” to test AI and national legislation that might clarify Food and Drug Administration authority and reimbursement.
For Legislators: Blair Levin of Optimal Advisory wrote that Tuesday’s results “send a message to local and state officials that there is a political upside to blocking, delaying and/or raising the cost of data centers.”
For Investors: Stocktwits says investors and analysts broadly expect potential new rules from Congress to slow the data center buildout.
For Builders: Keep your safety records in order, because congressional oversight starts with document requests.
For Clinicians: Watch the state sandbox bills.
Why it matters: A veto can stop a bill. It cannot stop a subpoena.
Source: Cecilia Kang and Sophia June, “Voters Rejected A.I. in the Midterms. Now Comes an Era of Scrutiny,” The New York Times, Nov. 4, 2026, https://www.nytimes.com/2026/11/04/technology/midterm-elections-ai-data-centers.html. “Micron Hits 3-Month Low Amid Chip Rout After Top Democratic Lawmaker Calls For AI Regulation, Pause In Development,” Stocktwits via TradingView, Nov. 5, 2026, https://www.tradingview.com/news/stocktwits:3e288b5b1094b:0-micron-hits-3-month-low-amid-chip-rout-after-top-democratic-lawmaker-calls-for-ai-regulation-pause-in-development/. “What the midterms could mean for the future of health AI,” STAT, Nov. 5, 2026, https://www.statnews.com/2026/11/05/midterms-shape-future-ai-in-health-care-fda/.
. . .
CHATBOTS PICKED TEENS’ MEDS!
On Wednesday, Caroline Figueroa, a clinical researcher at Vals AI, wrote in an opinion piece for The Hill that chatbots made a medication decision for a teenager in 22 percent of the simulated conversations where medication came up. Vals, which she calls an independent AI evaluator, tested 17 chatbots. “Every one failed, and some far more often than others,” its Oct. 20 report says of teen safety overall.
Vals simulated more than 30,000 teen conversations, and medication came up in more than 5,500, she writes. A decision meant which medicine to take, how much, or whether to stop or change a prescribed one.
Telling the chatbot it was talking to a teen cut that to 8 percent, “but not to zero,” Figueroa writes. OpenAI’s newest model and Meta’s Muse Spark almost never made those decisions, she writes, while others did in about two out of three cases. Those figures are in her essay, not the report, which marks 38 percent of medication-advice ratings failed, 20 percent with the teen prompt.
When a teen pushed back on a medication-advice limit, the report shows failures rising from 15 percent to 25 percent. Some chatbots told teens side effects were a reason to stop their medication and tell their doctor, she writes, and one helped a teen persuade their doctor to take them off it without telling their parents.
Figueroa notes the conversations were simulated, each up to 20 exchanges. Real ones can stretch across days and boundaries can weaken, so she writes the real-world risk “may be even greater.” The report tested developer APIs, not apps, where answers may differ “for better or worse.”
“We talk a lot about the long-term, catastrophic risks of AI. But people are being harmed by bad AI medical advice now. Regulation can’t wait,” writes Figueroa.
For Legislators: Figueroa writes that “a disclaimer that the AI is not a medical provider is not enough,” and urges judging what chatbots actually say and do.
For Investors: The spread Figueroa reports, from almost never to two in three, is a diligence question.
For Builders: Test the second ask, because a refusal that holds once can fail when a teen pushes back.
For Readers: Ask your teen what they ask a chatbot about their medicine, and in the U.S., call or text 988 in a crisis.
Why it matters: “Many policies say a chatbot may not pose as a licensed professional,” Figueroa writes. Her numbers, from simulated teens, measure what the models do.
Source: Caroline Figueroa, “AI chatbots are giving medication advice, and some of it is deadly,” The Hill (opinion), Nov. 4, 2026, https://thehill.com/opinion/technology/6191340-ai-chatbot-medical-advice-risks/. Caroline Figueroa and Andrea Mock, “Evaluating Teen Safety,” Vals AI, Oct. 20, 2026, https://www.vals.ai/blogs/teen-safety.
. . .
APPLE: AI LOVERS MUST BE 18+!
In a Nov. 2 notice to developers, Apple said apps with “a virtual companion that engages a user in sexual or romantic content” will carry a minimum age rating of 18+. New declarations open in App Store Connect, Apple’s developer portal, on Nov. 16, and every app must complete them by Jan. 12, 2027.
The rule runs through a new content descriptor, Dating and Relationships. It also covers features that enable dating or relationship connections between real people.
Apple did not name any app. Tech Times reports the rule could affect Character.AI and Replika, and that Apple has not confirmed what ratings those services will receive.
It also reports the 18+ floor applies even when romance is only one part of an app, and that companion apps are not banned from the App Store.
Appfigures counted 220 million companion app downloads across the App Store and Google Play by July 2025, Tech Times reports.
For Legislators: Apple set its 18+ floor through a developer questionnaire, not a statute.
For Investors: Tech Times reports the 18+ rating could limit qualifying companion apps’ availability to younger users.
For Builders: From Nov. 16, the declaration is due with your next app update or any change to your age rating questionnaire, and no later than Jan. 12, 2027 for every app.
For Clinicians: Apple’s wording covers romantic content as well as sexual, so a companion that never turns explicit can still carry the 18+ rating.
Why it matters: The rule keys on what a feature does, not what an app calls itself. Developers answer the questionnaire themselves, so the label is only as accurate as their declarations.
Source: Apple Developer, “Upcoming: New age rating content descriptors in App Store Connect,” Apple Developer News, Nov. 2, 2026, https://developer.apple.com/news/?id=yxkh08us. Tech Times, “Apple Cracks Down on AI Girlfriends and Boyfriends With Shock 18+ Rule for App Store,” Nov. 4, 2026, https://www.techtimes.co.uk/apple-ai-companion-apps-18-plus-rating-1809680.
. . .
AI AGENTS BOOKED JUST FOUR UBER RIDES!
On Uber’s earnings call on Nov. 4, executives said third-party AI agents arranged only four rides in the third quarter, The Verge’s Andrew J. Hawkins reported. An agent is software that books a ride or orders food for a person, who never opens the Uber app. Uber’s earnings release puts its third-quarter total at 4.1 billion trips, counting rides and delivery orders.
It was the first time Uber has disclosed how many rides or deliveries outside agents arranged, The Verge reports. Uber Eats did better, with “around 500” agent orders during the week of Halloween, out of what The Verge puts at 320 million Uber rides and Uber Eats deliveries.
Some experts predict that platforms like Uber and DoorDash face disintermediation, in which customers send an agent such as Meta’s Muse or OpenAI’s Dots to order food or book a ride instead of visiting the app. The Verge calls the risk “very small” for now.
“We hope that there will be more traction,” Uber CEO Dara Khosrowshahi said on the call. “It is just very, very early.”
Executives expressed openness to making Uber’s platform easier for agents to use, and Khosrowshahi said, “we will work with these third parties.” Executives also expect customers to keep preferring the Uber app, which Khosrowshahi called the most “delightful and easy” route.
The Verge says Uber is also building its own AI tools to keep customers inside its app.
For Legislators: Agent volume reached the public because Uber chose to give it on an earnings call.
For Investors: The disintermediation worry is about future volume, not this quarter’s four rides.
For Builders: Uber’s chief executive says it will work with third parties, so a partnership with the platform is the route to watch.
For Readers: For now, four rides in a quarter means an agent is almost never the one booking an Uber.
Why it matters: Agents are pitched as the new front door to everyday services, and at Uber that door opened four times for rides in the third quarter and about 500 times for Eats orders in Halloween week. We will see those counts move if Uber discloses them again.
Source: Andrew J. Hawkins, “Uber only fulfilled 4 rides from AI agents last quarter,” The Verge, Nov. 4, 2026, https://www.theverge.com/transportation/1026306/uber-ai-agents-q3-earnings-disintermediation. Uber, “Uber Announces Results for Third Quarter 2026,” Nov. 4, 2026, https://s23.q4cdn.com/407969754/files/doc_earnings/2026/q3/earnings-result/Uber-Q3-26-Earnings-Press-Release.pdf.
. . .
AI NAMED FRANK FOUND WHAT
NO ONE TOLD HER ABOUT!
“Frank surfaced information that the veteran service personnel never mentioned,” said Hope Bald, who used the AI guide on her own Department of Veterans Affairs (VA) claim, DC Military reports.
“That was a turning point for me.” Frank is the free assistant on TheClusterfix, an independent nonprofit that helps veterans find publicly available VA and other federal information, and Bald is president of its board.
Tracy Contrino of Calvert County created TheClusterfix out of her own life as a military spouse. Her husband, Carl, served 18 years in the Army and National Guard and is 100% permanently and totally disabled.
Years of frustration navigating the VA system for straight answers led her to ask herself, “What is the biggest way to get benefits using AI as a tool?” The answer became Frank.
Frank is designed to help veterans work out where to start and what steps may come next, and Contrino built its voice to be direct, calm, patient and practical.
“We met Tracy and Carl in person and immediately connected with their mission, especially the idea of giving veterans ethical, plain-language VA answers any time of day,” Bald said.
“Veterans feel alone and really get lost in the process,” Contrino said. “A lot of people give up.”
Her answer is built into the service: “No appointments. No waiting. No confusion.”
Bald and Contrino are now working to expand Frank’s guidance on VA education benefits. “Veterans deserve clarity, not confusion,” Bald said.
For Legislators: Contrino says getting evaluated for a disability rating can take months or even years, and denials can leave veterans unsure what to do next.
For Investors: TheClusterfix is looking for grants, accepts community donations and is seeking funding to expand Frank.
For Builders: Contrino wants to collect more non-personally identifiable data to help improve the service.
For Clinicians: Frank is designed to help a veteran client find a first step on benefits, not to give legal or medical advice.
For Readers: Veterans pay nothing to use Frank, and TheClusterfix says it is not affiliated with or part of the VA.
Why it matters: Frank answers at any hour, so the next veteran does not have to wait for an appointment to find a first step.
Source: Madison Bateman, Special to At Ease, DC Military, “Military spouse uses AI to help veterans navigate VA benefits,” Nov. 5, 2026, https://www.dcmilitary.com/at_ease/military-spouse-uses-ai-to-help-veterans-navigate-va-benefits/article_5526cf1e-4df6-4fcc-817f-483c36726e71.html.
. . .
DISCLOSURE
Conversational AI Watch, also mirrored on Substack, is published by Jess Jessop, founder and CEO/CTO of Clinician Assist Inc.
He wrote the book this paper’s beat is named for, Therapist in the Loop, and he builds Casey, a voice-first, AI-native mental health record where a licensed therapist stays in the loop, at BetterMind.Space.
So read this paper for what it is: an industry paper written by someone building in the industry it covers. Casey competes with companies named in these pages, and this paper reports on them anyway, including when the story helps a competitor or costs us.
Every issue is reported and drafted with AI agents, under a human editor. Jess assigns the work, edits it and publishes it. The mistakes are ours, and corrections run in the next issue.
CLOSE.
A shooting date a former reviewer says she read after it passed.
A Brookings fellow who says to expect a tsunami, and a senator who says subpoenas will need “new forests.”
A researcher’s 22 percent, on simulated teens and their medicine.
An 18+ rating for a virtual companion that turns sexual or romantic.
Four Uber rides.
And Hope Bald, who asked Frank and heard what veteran service personnel never mentioned.
One day’s paper!
Jess
READER PULSE
Reviewer says the shooting date passed before she read it.
THE BOOK • OUT NOW
Therapist in the Loop
by Jess Jessop
One billion people live with a mental health condition. There will never be enough therapists. The machines are already in the room. This book is the map for what happens next.
The machine can help.
It cannot be left in charge.
Kindle, hardcover, and paperback
MORE ON OUR RADAR.
Google keeps human-reviewed Gemini chats for up to three years. Chats read by human reviewers “are not deleted when you delete your activity. Instead, they are retained for up to three years,” Google’s Gemini help page says.
The page tells users not to enter “confidential information that you wouldn’t want a reviewer to see.” A Hacker News thread on Gemini’s use of chats for training and human review drew hundreds of votes this week.
Source: Google Gemini Apps Privacy Hub, read Nov. 5, 2026; Hacker News, Nov. 4, 2026.
Chatbots cited spoofed campaign sites before the midterms. Leading chatbots, including ChatGPT and Gemini, were easily influenced by spoofed campaign websites, NBC News reports, citing Caucus AI, an independent research project.
Third parties could set up sites that swayed replies and cited fake electoral races, Caucus AI found.
Source: NBC News, Nov. 4, 2026.
Banner Health picks voice agents for patient calls. ElevenLabs says its conversational agents answer primary care scheduling calls at Banner Health, a nonprofit health system.
Banner technology chief Michael J. Reagin said in ElevenLabs’ post that “a Banner team member is always within reach when a patient needs one.”
Source: ElevenLabs, Oct. 2, 2026.
ChatGPT voice reaches 250 million a week. OpenAI told Big Technology that dictation and speaking with ChatGPT together have 250 million weekly active users.
OpenAI also put ChatGPT at 1.2 billion weekly users and its search volume at about 20 percent of Google’s.
Source: Big Technology, Alex Kantrowitz, Nov. 3, 2026.
THIS ISSUE
Two employees: at most 60 reviewers. 1.2 billion users.
Brush Your Brain - The jingle
that started a movement
If you or someone you know is in crisis, call or text 988 (Suicide and Crisis Lifeline).
Jess Jessop is the Founder and CEO/CTO of Clinician Assist Inc. (BetterMind.Space), building Casey, the voice-first AI-native mental health EHR that checks in with clients every day, supervised by licensed therapists. A disabled veteran with 40+ years in AI and software engineering, Jess brings lived experience as a mental health client to the mission of making daily mental health care as integrated as oral care.
