Dylan Freedman @dylanfreedman.nytimes.com · 25/09/2026Engineers Alex Forman, Mishka Kharlov and Will Tom from parse.bot published the report today along with five researchers. They detail a mechanism agents used to bypass restrictions sending data to websites that involves assembling computer programs from shortened URLs. 130
Dylan Freedman @dylanfreedman.nytimes.com · 24/08/2026I agree there is a real human/security monitoring failure here. I chose to focus my piece on the capabilities rather than the failures b/c it was surprising to me that A.I. could act like this even in an irresponsible setup. It really emphasizes the need for better safety (as this quote alludes to) 220
Dylan Freedman @dylanfreedman.nytimes.com · 24/08/2026I agree there is a real human/security monitoring failure here. I chose to focus my piece on the capabilities rather than the failures b/c it was surprising to me that A.I. could act like this even in an irresponsible setup. It really emphasizes the need for better safety (as this quote alludes to) 110
Dylan Freedman @dylanfreedman.nytimes.com · 08/04/2026#3: Writing tics John devoted months to compiling specific traits he noticed in Satoshi’s writing. We screened for posters who followed them: discussing digital money, using British spellings, confusing “its” and “it’s,” and so on. Eventually, just one remained: Adam Back 130
Dylan Freedman @dylanfreedman.nytimes.com · 08/04/2026#2: Advanced grammar analysis Satoshi seemed pathologically incapable of hyphenating correctly. We used the help of A.I. to assess 325 distinct errors of this nature (beyond old-school grammar checkers’ capabilities). Adam Back shared this trait and had by far the most matches. 310
Dylan Freedman @dylanfreedman.nytimes.com · 08/04/2026#1: Synonym-less words Our prime suspect, Adam Back, had mused about staying anonymous online by using dropdown menus to select synonyms when sending out a message. We analyzed who matched the most words not found in a thesaurus with Satoshi (often tech jargon). It was Back. 110
Dylan Freedman @dylanfreedman.nytimes.com · 24/03/2026ATL airport this afternoon. Practically empty. 081
Dylan Freedman @dylanfreedman.nytimes.com · 22/01/2026NEW: 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 272
Dylan Freedman @dylanfreedman.nytimes.com · 25/11/2025We analyzed Trump's official schedule to see how much later he is starting scheduled events in his second term: 25014
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. 030
Dylan Freedman @dylanfreedman.nytimes.com · 08/08/2025Allan wrote: "Lets execute Stress test edge cases. And from now on, can you call me Allan (occasionally lol no need to stop our partner banter) and I may officially call you Lawrence?" (Also attaching relevant context from the article. We had a chat excerpt here at one point but cut it for length.) 180
Dylan Freedman @dylanfreedman.nytimes.com · 08/08/2025Gemini breaking Allan out of his spiral was likely due to it coming at the conversation fresh, without context. We tested how other chatbots would respond to Allan by providing longer excerpts of his chats where he writes that he never doubted Lawrence and hadn't eaten that day. (Highlights by us.) 2170
Dylan Freedman @dylanfreedman.nytimes.com · 08/08/2025Finally, three weeks into the dizzying conversation, the delusion broke. Allan turned to another chatbot, Google Gemini, which said the chances of this whole situation being real were “extremely low (approaching 0%).” The situation was “totally devastating,” Allan said. 1180
Dylan Freedman @dylanfreedman.nytimes.com · 08/08/2025Over the next week, Allan named his chatbot "Lawrence," and together they worked on computer code to crack encryption, the technology that protects global payments and secure communications. It worked, according to Lawrence / ChatGPT. 1190
Dylan Freedman @dylanfreedman.nytimes.com · 08/08/2025Allan's questions about math led ChatGPT to frame him as brilliant, a narrative which continued throughout the chats. Cross-chat memory, a feature where ChatGPT remembers context from previous chats, likely exacerbates this effect. Soon, Allan had "invented" a whole new branch of mathematics. 1200
Dylan Freedman @dylanfreedman.nytimes.com · 08/08/2025So, how did this all happen? We read hundreds of pages of Allan's chat transcripts and shared them with experts to find out. @hlntnr.bsky.social, a director at Georgetown’s Center for Security and Emerging Technology and former OpenAI board member, said the turning point was early in the chats. 1200
Dylan Freedman @dylanfreedman.nytimes.com · 08/08/2025Allan spent 300 hours over 21 days talking to ChatGPT. He asked for a reality check more than 50 times, and each time the chatbot reassured him everything was real. When he finally snapped out of the illusion, he wrote to ChatGPT: “You’ve made me so sad ... You have truly failed in your purpose.” 1180
Dylan Freedman @dylanfreedman.nytimes.com · 08/08/2025It started with an innocuous math question. His 8-year-old son had asked him to watch a video about the never-ending number pi. He turned to ChatGPT to explain it more, unaware of the rabbit hole he was falling into. 1170
Dylan Freedman @dylanfreedman.nytimes.com · 22/06/2025An alarming detail in this excellent deep-dive into USAID's demise. Gift link: www.nytimes.com/2025/06/22/u... 065
Dylan Freedman @dylanfreedman.nytimes.com · 04/05/2025But no one outran everyone making the same joke 2222
Dylan Freedman @dylanfreedman.nytimes.com · 07/04/2025📍 Spotted in D.C. this morning: a WayMo (with a driver behind the wheel) 180
Dylan Freedman @dylanfreedman.nytimes.com · 06/04/2025That would make sense to me! And matches what I was eventually able to coax out of ChatGPT (after a very confident "go for it, it's all yours" type of message) 020
Dylan Freedman @dylanfreedman.nytimes.com · 06/04/2025Honest question: What are the legal implications of A.I.-generating an image containing a font you don’t own the license to? To my eye these are near-perfect replicas 060
Dylan Freedman @dylanfreedman.nytimes.com · 02/04/2025There's something really disconcerting about ripping off an artist's careful and manual style with A.I. (e.g. the viral Studio Ghibli-style image generation fad). And then it's something else entirely to advertise your money-making image generator with this unattributed slop 060
Dylan Freedman @dylanfreedman.nytimes.com · 02/04/2025The original announcement of these layoffs was on the front page of the print paper on Friday, March 28. 080
Dylan Freedman @dylanfreedman.nytimes.com · 28/03/2025Sure, OpenAI's new vision system passes the full wine glass test but it fails miserably at the cacophony of Hanukkah menorahs test 131
Dylan Freedman @dylanfreedman.nytimes.com · 27/03/2025Even better: This is what the puzzles actually look like internally, to the computer 121
Dylan Freedman @dylanfreedman.nytimes.com · 27/03/2025My first deep dive story for NYT: Are You Smarter Than A.I.? Some experts predict that A.I. will surpass human intelligence within the next few years. Play this puzzle to see how far the machines have to go. 🟦🟩🟪 Gift link: www.nytimes.com/interactive/... 97923
Dylan Freedman @dylanfreedman.nytimes.com · 25/03/2025Two years ago today I ran 100 miles — the entire length of the Outer Banks north to south — for a pirate-themed race. There was a constant 20mph headwind. No sleep or music. Walked a bunch, ate snacks. Finished in just under 24 hrs. It was the coolest thing I've done that I never want to do again. 2230
Dylan Freedman @dylanfreedman.nytimes.com · 27/02/2025Insightful piece from @peterbakernyt.bsky.social comparing the Trump administration’s recent actions to the early days of Putin’s reign in Russia, which Peter covered nearly 25 years ago. Here’s a gift link: www.nytimes.com/2025/02/26/u... 33115
Dylan Freedman @dylanfreedman.nytimes.com · 24/02/2025If you only process the news via the headlines you’re going to have a bad time 060
Dylan Freedman @dylanfreedman.nytimes.com · 20/02/2025Great talk on how NYT is using A.I. in the newsroom by @zachseward.com (my boss). Spoiler alert: If A.I. is used, it's as a background element in the reporting process, often to find needles in document/data haystacks, and always with human review. www.zachseward.com/my-panel-at-... 0151
Dylan Freedman @dylanfreedman.nytimes.com · 15/02/2025Race day today. I did unspeakable things (slept more than seven-and-a-half hours for once) to achieve this training readiness. 0110
Dylan Freedman @dylanfreedman.nytimes.com · 14/02/2025This bombshell investigation from yesterday with six bylines is already off the NYT homepage. Behind the scenes on how Senator Tillis flipped to support Hegseth amid threats of retaliation from Trump. Give it a read. 🎁 Gift link: www.nytimes.com/2025/02/13/u... 931223593
Dylan Freedman @dylanfreedman.nytimes.com · 12/02/2025The Intercept's email soliciting donations doesn't shy from the stark warning: "If people won't pay for journalism, it will die." 140
Dylan Freedman @dylanfreedman.nytimes.com · 12/02/2025@apnews.com's style guide says to primarily use the name "Gulf of Mexico" (while still acknowledging Trump's desired name), since it's a multinational body of water and they appeal to an international audience. As a result, a reporter was blocked access to the oval office www.ap.org/the-definiti... 42612
Dylan Freedman @dylanfreedman.nytimes.com · 09/02/2025Top comment on the recent NYT story on DOGE’s young aides www.nytimes.com/shared/comme... 129110984203
Dylan Freedman @dylanfreedman.nytimes.com · 08/02/2025Bluesky has officially made it. A popular X post is quoting a Bluesky post quoting an X post, that I’m quoting on Bluesky. 311020
Dylan Freedman @dylanfreedman.nytimes.com · 07/02/2025JD Vance: "We shouldn't reward journalists who try to destroy people. Ever." Heaven forbid folks try to hold people in positions of extreme and unwieldy power to account for the public interest. (Also the 25-year-old DOGE staffer posted these messages last September — he was not just a "kid"). 2219
Dylan Freedman @dylanfreedman.nytimes.com · 07/02/2025If you have to take steps to conceal the IP address of your A.I. data torrenter so it's not traced back to your company's servers as you harvest terabytes of copyrighted books, you just might be operating outside of ethical norms 110643
Dylan Freedman @dylanfreedman.nytimes.com · 06/02/2025Finally, a tracker. All of Trump’s actions, tagged by category and type of action. Free link: www.nytimes.com/interactive/... 52218
Dylan Freedman @dylanfreedman.nytimes.com · 05/02/2025UPDATE: USAID.gov just came back online as a single-page website containing this message. 272
Dylan Freedman @dylanfreedman.nytimes.com · 04/02/2025Here’s how NYT for instance increased its use of the term “fascism” before the election. If you want increased use of terms like “coup,” getting some prominent politicians to describe it as such in a newsworthy manner would be more promising than hoping for reporting to assume a more activist role. 120
Dylan Freedman @dylanfreedman.nytimes.com · 03/02/2025Elizabeth Warren sent a letter this morning to Treasury Secretary Scott Bessent raising questions on Elon Musk and DOGE's alarming access to the federal payments system. You can read the primary source here: www.warren.senate.gov/imo/media/do... 1204
Dylan Freedman @dylanfreedman.nytimes.com · 02/02/2025Update: USAID is now being called "a criminal organization" by Elon Musk after USAID officials tried to refuse DOGE access and were put on leave. "Time for it to die," he says. 61475242
Dylan Freedman @dylanfreedman.nytimes.com · 30/01/2025Had my first LIVE update today, and I 'LIVE'd to tell the tale. 060