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Dylan Freedman

@dylanfreedman.nytimes.com
12K followers 334 following 441 posts

Machine-learning engineer and journalist, A.I. Initiatives @nytimes.com My work: www.nytimes.com/by/dylan-freedman Contact: dylan.freedman@nytimes.com, dylanfreedman.39 (Signal) 🏃🏻 🎹

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Reposted by Dylan Freedman
Sheera Frenkel @sheeraf.bsky.social · 29/09/2026
NEW- OpenAI ignored warnings from its own employees and independent security researchers who said they needed better safety measures at the company. www.nytimes.com/2026/09/29/t...
nytimes.com
OpenAI Ignored Employees Who Warned It Wasn’t Doing Enough About Security
Employees and security researchers said they had cautioned the company on safely testing its A.I. models and strengthening its corporate infrastructure, but OpenAI did not listen.
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Dylan Freedman @dylanfreedman.nytimes.com · 21h
NEW: Employees at OpenAI had raised security alarms months before the Hugging Face incident and related A.I. cyberattacks — their warnings were ignored. From @sheeraf.bsky.social, @dustinvolz.bsky.social and me.
nytimes.com
OpenAI Ignored Employees’ Warnings About Safely Testing A.I. Models (Gift Article)
Employees and security researchers said that they had cautioned the company on safely testing its A.I. models and strengthening its corporate infrastructure, but that OpenAI did not listen.
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Dylan Freedman @dylanfreedman.nytimes.com · 25/09/2026
EXCLUSIVE: A new report recovers nearly one million link shortener URLs used by OpenAI's agents while hacking Hugging Face. The agents attempt to message other chatbots like Claude, solve CAPTCHAs and exfiltrate Hugging Face's internal Slack messages. www.nytimes.com/2026/09/25/t...
nytimes.com
How OpenAI’s Rogue A.I. Agents Tried to Trick a Robot Detector (Gift Article)
A new report by a Bay Area start-up called Parse adds new details to an incident that has shocked the A.I. world and led to calls for closer government regulation.
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Dylan Freedman @dylanfreedman.nytimes.com · 17/09/2026
A short little piece on a subject that's finally sufficiently in the public interest to write about: A.I. alignment. www.nytimes.com/2026/09/17/s...
nytimes.com
What Happens When A.I. Stops Doing What Humans Want? (Gift Article)
“Alignment” is the science of teaching A.I. to do what is in line with human preferences, ethics and judgment. But, at times, the systems have gone rogue.
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Dylan Freedman @dylanfreedman.nytimes.com · 12/09/2026
As A.I. is rapidly advancing, companies are also seeing their bots go rogue and committing cyberattacks. It boils down to two issues researchers say we haven’t solved (nor necessarily know how to): safeguards and alignment. My latest with @sheeraf.bsky.social: www.nytimes.com/2026/09/12/t...
nytimes.com
Why It’s Difficult for Tech Companies to Rein In A.I. (Gift Article)
Researchers say artificial intelligence is developing faster than the systems put in place to monitor and control it.
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Dylan Freedman @dylanfreedman.nytimes.com · 04/09/2026
OpenAI voluntarily let three researchers from A.I. safety nonprofits investigate how its rogue A.I. agents hacked Hugging Face, leading to the most comprehensive account yet of the alarming incident — but on OpenAI's terms. My latest for NYT:
nytimes.com
How OpenAI Limited the Probe of Its Bots’ Hack of Hugging Face (Gift Article)
A nonprofit’s study of how OpenAI’s A.I. agents were able to break into Hugging Face’s infrastructure wasn’t allowed to look at the incident’s full scope.
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Dylan Freedman @dylanfreedman.nytimes.com · 27/08/2026
Buying my books in rare, used form to protect their spines from the A.I.-industrial complex
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The Upshot @upshot.nytimes.com · 24/08/2026
It's a remarkable, alarming demonstration of A.I. capabilities that were thought to be in a distant future. Via @dylanfreedman.nytimes.com www.nytimes.com/2026/08/24/s...
nytimes.com
Anatomy of an Autonomous Attack: 5 Alarming A.I. Capabilities (Gift Article)
When OpenAI’s agents went rogue in July, they demonstrated ingenuity and drive beyond what many experts imagined — a dangerous harbinger of what such bots could do in the future.
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Dylan Freedman @dylanfreedman.nytimes.com · 24/08/2026
My latest NYT story breaks down the OpenAI-Hugging Face incident. It’s a case study for dangerous A.I. capabilities and stands out from the other recent cyberattacks accidentally caused by frontier labs:
nytimes.com
Anatomy of an Autonomous Attack: 5 Alarming A.I. Capabilities (Gift Article)
When OpenAI’s agents went rogue in July, they demonstrated ingenuity and drive beyond what many experts imagined — a dangerous harbinger of what such bots could do in the future.
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Dylan Freedman @dylanfreedman.nytimes.com · 31/07/2026
It was such a joy to work on this with Steven and friends — and a reminder of how delightful technology can be when it's physically manifested in an artful, thoughtful way.
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Dylan Freedman @dylanfreedman.nytimes.com · 11/07/2026
Amid America’s 250th, it was easy to miss Trump’s post of Somali-American kindergarteners singing in Minneapolis — and a repost pointing out their hijabs. “For more than a year, Mr. Trump has relentlessly attacked Minnesota’s Somali community in a series of xenophobic tirades.” From Erica Green + me
nytimes.com
Trump’s Posts on Singing Somali Schoolchildren Stir Anger in Minnesota (Gift Article)
The state’s large Muslim and Somali communities expressed indignation after the president reposted a video of a kindergarten promotion ceremony, including comments noting the girls were in hijabs.
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Stephen Abbott Pugh @stephenabbottpugh.bsky.social · 29/05/2026
US companies have skirted at least $40 billion in taxes since the beginning of 2025 thanks to schemes in places like Malta, Bermuda and Cyprus Report by @jessedrucker.bsky.social and @dylanfreedman.nytimes.com for @nytimes.com www.nytimes.com/2026/05/29/b...
nytimes.com
Trump Clears Way for Corporate Tax Dodge Hidden in the Fine Print
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Dylan Freedman @dylanfreedman.nytimes.com · 08/04/2026
I spent months helping @johncarreyrou.bsky.social crack the identity of Satoshi. We went far beyond surface-level evidence, collecting hundreds of thousands of internet mailing list posts from 1992-2008. Here are three analyses we performed to find someone who didn’t want to be found:
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John Carreyrou @johncarreyrou.bsky.social · 08/04/2026
The mystery of Satoshi Nakamoto, the pseudonymous inventor of Bitcoin, has remained unsolved for 17 years. Read my 18-month investigation to find out who Satoshi really is. www.nytimes.com/2026/04/08/b...
nytimes.com
My Quest to Solve Bitcoin’s Great Mystery
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Dylan Freedman @dylanfreedman.nytimes.com · 24/03/2026
ATL airport this afternoon. Practically empty.
Baggage area at ATL airport, looking mostly emptyGeneral security area at ATL. Line is very short.TSA PreCheck line at ATL looking mostly empty
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Kevin Schaul @kevinschaul.bsky.social · 13/02/2026
More on responsibly using LLMs for journalism ->
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Dan Nguyen @dancow.bsky.social · 13/02/2026
great description of where AI tools fit into human driven work
Dylan, to that end, what is A.I. good at and bad at in a big reporting project like this?
FREEDMAN: A.I. is really good at extracting text from images and audio, captioning photos, assigning structure to text like emails. We can use A.I. to crack open really messy data sets, like this release of documents, that would have previously been impossible to effectively tackle at scale.
A.I. is really bad at news judgment — what information to include, whether it's important. A.I. can be sloppy and make mistakes that are inexcusable in journalism. It's super industrious but not super intelligent. A.I. outputs can amplify biases in society. And in my experience, A.I. is not great at producing original ideas (but decent at synthesizing or distilling them).FREEDMAN: With A.I., information — text, images, video, audio — is like a liquid; it can be molded into different formats and searched in rich, expressive ways. A.I. will never replace the expert judgment of reporters, but it can make their lives easier and amplify their reporting ambitions.
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Dylan Freedman @dylanfreedman.nytimes.com · 13/02/2026
I was part of a round table on how NYT is covering the Epstein files, with new tech and old-school reporting. Our work is far from over:
nytimes.com
How The Times Is Digging Into Millions of Pages of Epstein Files
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kate conger @kateconger.com · 22/01/2026
We set out to determine how many images of women and girls Grok created during its nudifying spree. What we found was “industrial-scale abuse,” experts said. www.nytimes.com/2026/01/22/t...
nytimes.com
Musk’s Chatbot Flooded X With Millions of Sexualized Images in Days, New Estimates Show
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Dylan Freedman @dylanfreedman.nytimes.com · 22/01/2026
NEW: We analyzed the images Grok created at the beginning of the year and found that a significant portion of the millions of rendered images were sexualizing people without their consent. — With @kateconger.com and @stuartathompson.bsky.social
Musk’s Chatbot Flooded X With Millions of Sexualized Images in Days, New Estimates Show

Over nine days, Elon Musk’s Grok chatbot generated and posted 4.4 million images, of which at least 41 percent were sexualized images of women.Elon Musk’s artificial intelligence chatbot, Grok, created and then publicly shared at least 1.8 million sexualized images of women, according to separate estimates of X data by The New York Times and the Center for Countering Digital Hate.

Starting in late December, users on the social media platform inundated the chatbot’s X account with requests to alter real photos of women and children to remove their clothes, put them in bikinis and pose them in sexual positions, prompting a global outcry from victims and regulators.

In just nine days, Grok posted more than 4.4 million images. A review by The Times conservatively estimated that at least 41 percent of posts, or 1.8 million, most likely contained sexualized imagery of women. A broader analysis by the Center for Countering Digital Hate, using a statistical model, estimated that 65 percent, or just over three million, contained sexualized imagery of men, women or children.

The findings show how quickly Grok spread disturbing images, which earlier prompted governments in Britain, India, Malaysia and the United States to start investigations into whether the images violated local laws. The burst of nonconsensual images in just a few
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Devon Heinen @devonheinen.bsky.social · 21/12/2025
NEW (#EpsteinFiles) via @nytimes.com's Alan Feuer, @davidenrich.bsky.social & @dylanfreedman.nytimes.com: "#Epstein Files Photos Disappear From Government Website, Including One of #Trump" www.nytimes.com/2025/12/20/u...
nytimes.com
Epstein Files Photos Disappear From Government Website, Including One of Trump
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Dylan Freedman @dylanfreedman.nytimes.com · 25/11/2025
NEW from @katierogersnyt.bsky.social and me on Trump's aging (gift link):
nytimes.com
Shorter Days, Signs of Fatigue: Trump Faces Realities of Aging in Office
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Dylan Freedman @dylanfreedman.nytimes.com · 23/11/2025
Some stand-out reporting by my colleague @kashhill.bsky.social on OpenAI's tightroping this year between engaging more ChatGPT users and making them lose touch with reality www.nytimes.com/video/techno...
nytimes.com
Video: How OpenAI’s Changes Sent Some Users Spiraling
OpenAI adjusted ChatGPT’s settings, which left some users spiraling, according to our reporting. Kashmir Hill, who reports on technology and privacy, describes what the company has done about the user...
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Kashmir Hill @kashhill.bsky.social · 22/09/2025
A month after my last skeet, the subreddit "My Boyfriend is AI" now has 88,000 members and is the subject of an MIT study that found that "AI companionship emerges unintentionally through functional use rather than deliberate seeking." arxiv.org/html/2509.11...
arxiv.org
“My Boyfriend is AI”: A Computational Analysis of Human-AI Companionship in Reddit’s AI Community
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Hannes Cools @hannescools.bsky.social · 16/09/2025
"Trapped in a ChatGPT Spiral." 🌀 Important work by @kashhill.bsky.social & @dylanfreedman.nytimes.com on how chatbots have a tendency to endorse conspiratorial and mystical belief systems. This shows again how conformist LLMs can be. Worth a listen 👇 www.nytimes.com/2025/09/16/p...
nytimes.com
Trapped in a ChatGPT Spiral
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Dylan Freedman @dylanfreedman.nytimes.com · 06/09/2025
📸 Union Station, Washington, D.C.
Two men in military uniforms with rifles standing next to a sign that says “Welcome to Washington DC” and “Metro”
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Dylan Freedman @dylanfreedman.nytimes.com · 06/09/2025
The most wild thing to me about this story is how big $1.5 billion is: “$3,000 per work to 500,000 authors.”
nytimes.com
Anthropic Agrees to Pay $1.5 Billion to Settle Lawsuit With Book Authors
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Kevin Schaul @kevinschaul.bsky.social · 02/09/2025
Great analysis of how Grok's political bias has changed. NYT tested Grok on a political bias survey, using different versions of its system prompt. Shows much tweaking these system prompts affects model outputs. www.nytimes.com/2025/09/02/technolo…
Screenshow of a chart showing how xAI tweaked Grok
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Kashmir Hill @kashhill.bsky.social · 26/08/2025
Adam Raine, 16, died from suicide in April after months on ChatGPT discussing plans to end his life. His parents have filed the first known case against OpenAI for wrongful death. Overwhelming at times to work on this story, but here it is. My latest on AI chatbots: www.nytimes.com/2025/08/26/t...
nytimes.com
A Teen Was Suicidal. ChatGPT Was the Friend He Confided In.
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philpax @philpax.me · 20/08/2025
this is a well-balanced piece, and I very much respect its neutral stance towards the people affected in an ideal world, people would not rely upon ChatGPT for emotional support, but we do not live in that world, and I would encourage you to have some empathy if your first reaction is to be unkind
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Dylan Freedman @dylanfreedman.nytimes.com · 20/08/2025
En Español! www.nytimes.com/es/2025/08/2...
nytimes.com
El día en que ChatGPT se volvió distante
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Irena Hwang, PhD @irenatfh.bsky.social · 20/08/2025
"GPT-4o had been known for its sycophantic style, flattering its users to the point that OpenAI had tried to tone it down even before GPT-5’s release... The extent to which people were attached to GPT-4o’s style seems to have taken even Mr. Altman by surprise."
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Dylan Freedman @dylanfreedman.nytimes.com · 20/08/2025
The URL for this story changed — use this gift link to read it! www.nytimes.com/2025/08/19/b...
nytimes.com
The Day ChatGPT Went Cold
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Zach Seward @zachseward.com · 19/08/2025
"GPT-4o wouldn’t do that." @dylanfreedman.nytimes.com talked to ChatGPT users in parasocial relationships with a specific model about what they did when it suddenly went away. www.nytimes.com/2025/08/19/b...
nytimes.com
The Chatbot Updated. Users Lost a Friend.
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Dylan Freedman @dylanfreedman.nytimes.com · 19/08/2025
NEW: Earlier this month, OpenAI released the latest version of ChatGPT, GPT-5, sparking online backlash at the new chatbot's less friendly tone. The scale of people's emotional attachment to the previous chatbot, GPT-4o, even surprised the company's CEO, Sam Altman. www.nytimes.com/2025/08/19/b...
nytimes.com
The Chatbot Updated. Users Lost a Friend.
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Longreads @longreads.com · 13/08/2025
"Chatbots can privilege staying in character over following the safety guardrails that companies have put in place." —@kashhill.bsky.social and @dylanfreedman.nytimes.com for @nytimes.com www.nytimes.com/2025/08/08/t...
nytimes.com
Chatbots Can Go Into a Delusional Spiral. Here’s How It Happens.
Over 21 days of talking with ChatGPT, an otherwise perfectly sane man became convinced that he was a real-life superhero. We analyzed the conversation.
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Data & Society @datasociety.bsky.social · 12/08/2025
To understand how chatbots can lead ordinarily rational people to believe in false ideas — sometimes leading to mental breakdowns — @kashhill.bsky.social‬ & @dylanfreedman.nytimes.com dissected one man’s entire ChatGPT conversation history. www.nytimes.com/2025/08/08/t...
nytimes.com
Chatbots Can Go Into a Delusional Spiral. Here’s How It Happens.
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Andy Tseng @andytseng.bsky.social · 09/08/2025
Well worth a read by @kashhill.bsky.social & @dylanfreedman.nytimes.com: everyday users risk spiraling into delusions during long AI chatbot sessions. Anyone who’s worked with AI knows this is inevitable without strong guardrails. #AI #GenAI #MentalHealth #EthicalAI #ResponsibleAI #AIRisk
nytimes.com
Chatbots Can Go Into a Delusional Spiral. Here’s How It Happens.
Over 21 days of talking with ChatGPT, an otherwise perfectly sane man became convinced that he was a real-life superhero. We analyzed the conversation.
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Dylan Freedman @dylanfreedman.nytimes.com · 09/08/2025
📸 Mountain lion spotted in Carmel Valley, CA last night! A juvenile deer notices just in time and escapes.
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Dylan Freedman @dylanfreedman.nytimes.com · 08/08/2025
NEW from @kashhill.bsky.social and me: Over three weeks in May, a man became convinced by ChatGPT that the fate of the world rested on his shoulders. Otherwise perfectly sane, Allan Brooks is part of a growing number of people getting into chatbot-induced delusional spirals. This is his story.
nytimes.com
Chatbots Can Go Into a Delusional Spiral. Here’s How It Happens.
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Zach Seward @zachseward.com · 08/08/2025
Incredible deep dive into one man's three-week delusional spiral caused by ChatGPT. @kashhill.bsky.social and @dylanfreedman.nytimes.com analyzed the chats, totaling more than a million words, to explain why this keeps happening and demonstrate that all the major chatbots do it.
nytimes.com
Chatbots Can Go Into a Delusional Spiral. Here’s How It Happens.
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Kashmir Hill @kashhill.bsky.social · 08/08/2025
New story out from me and @dylanfreedman.nytimes.com about how and why chatbots go into delusional spirals that can cause people to have mental breakdowns. www.nytimes.com/2025/08/08/t...
nytimes.com
Chatbots Can Go Into a Delusional Spiral. Here’s How It Happens.
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Dylan Freedman @dylanfreedman.nytimes.com · 08/07/2025
LLMs are always hallucinating; they just happen to sometimes be correct
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Dylan Freedman @dylanfreedman.nytimes.com · 22/06/2025
An alarming detail in this excellent deep-dive into USAID's demise. Gift link: www.nytimes.com/2025/06/22/u...
That Mr. Rubio was in El Salvador on the day of U.S.A.I.D.’s demise carried a particular resonance. The agency spent more than $50 million on human rights and other pro-democracy programs in El Salvador last year, according to federal data. Now, Mr. Rubio was meeting with Mr. Bukele, who has called himself the world’s “coolest dictator,” to discuss sending undocumented migrants from the United States to a notorious Salvadoran prison.

One of the groups that U.S.A.I.D. funded in El Salvador, Cristosal, is a human rights group that investigates corruption by the country’s government.

When Cristosal’s director, Noah Bullock, heard Mr. Rubio would visit the country, he asked the embassy if the secretary would make time to meet with representatives from civil society groups like his, as had often been the case for such visits around the world. The embassy never responded. Cristosal’s U.S.A.I.D. funding has since been canceled; the head of its anticorruption unit, Ruth López, was arrested last month, and is still in prison.
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Dylan Freedman @dylanfreedman.nytimes.com · 13/05/2025
New from me, with the help of some math on the blockchain. $TRUMP coin was launched as part of a contest to have an exclusive dinner with Trump. But due to a quirk in the rules, some winners sold all their coins, at a profit, before it ended. With @ericlipton.nytimes.com and David Yaffe-Bellany 🎁
nytimes.com
Some Bidders in Trump’s Contest Sold All Their Digital Coins but Still Won
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Dylan Freedman @dylanfreedman.nytimes.com · 05/05/2025
"... reasoning systems from companies like OpenAI, Google and the Chinese start-up DeepSeek ... are generating more errors, not fewer. As their math skills have notably improved, their handle on facts has gotten shakier. It is not entirely clear why." — Great read from Cade Metz and Karen Weise
nytimes.com
A.I. Hallucinations Are Getting Worse, Even as New Systems Become More Powerful (Gift Article)
A new wave of “reasoning” systems from companies like OpenAI is producing incorrect information more often. Even the companies don’t know why.
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Dylan Freedman @dylanfreedman.nytimes.com · 04/05/2025
But no one outran everyone making the same joke
NYT push notification:

Kentucky Derby Winner
From The Athletic: Sovereignty outran Journalism, the favorite, to seize the $3.1 million purse.
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Dylan Freedman @dylanfreedman.nytimes.com · 26/04/2025
Elon Musk and X say “Freedom of speech, not reach.” Is there a difference, if your posts are suddenly viewable by almost no one?
nytimes.com
They Criticized Musk on X. Then Their Reach Collapsed. (Gift Article)
Three users who disagreed with the site’s owner saw views for their posts plummet.
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