OpenAI's big privacy problem

Good morning, AI enthusiasts. OpenAI’s NYT copyright battle just turned into a privacy nightmare — with a court order forcing the AI leader to retain millions of private (and even deleted) user conversations.

With CEO Sam Altman proposing “AI privilege” and the tech moving towards deeper digital relationships with always-listening devices, this legal fight may set the stage for a new era of digital rights.

In today’s AI rundown:

• OpenAI fights court to preserve convos

• AI policy head weighs in on human-AI bonds

• How to turn complex research into quizzes

• AI reveals Dead Sea Scrolls are a century older

• 4 new AI tools & 4 job opportunities

LATEST DEVELOPMENTS

OPENAI

🔒 OpenAI fights court to preserve convos

The Rundown: OpenAI is pushing back against a recent court order stemming from its ongoing legal battle with The New York Times, which forces the company to retain all user conversations — including deleted chats.

The details:

• The mandate affects hundreds of millions of ChatGPT users across its free, Plus, Pro, and Team tiers, forcing OpenAI to retain even manually deleted chats.

• The New York Times argued for the data preservation out of concern that users might be infringing on its content and then deleting the evidence of their chats.

• CEO Sam Altman called the demand an "inappropriate request that sets a bad precedent" and proposed "AI privilege" similar to doctor-patient confidentiality.

• ChatGPT Enterprise, Edu, and API customers that use a Zero Data Retention agreement are excluded from the court order.

Why it matters: This order arrives at a moment when millions are starting to trust AI with vulnerable thoughts and information (for better or worse) — threatening to shatter trust just as it becomes embedded in daily life. The privacy question will become even thornier as AI transitions to physical devices with always-on recording capabilities.

TOGETHER WITH CONVEYOR

🛠️ AI was made for this

The Rundown: It's 2025 — security questionnaires should complete themselves, your customers should access your Trust Center instantly, and your content library shouldn't be a maintenance burden Sue and Phil, Conveyor's AI Agents, deliver exactly that with 95%+ accuracy.

Let Sue and Phil do the busy work so you can:

• Spend 90% less time answering security questionnaires and RFPs

• Skip the manual updates—your content library stays current on its own

• Give your customers instant AI answers in your Trust Center

• Fully automate admin and collaboration tasks across teams and tools

Learn more and put Conveyor’s AI agents to work.

OPENAI

🤗 AI policy head weighs in on human-AI bonds

The Rundown: OpenAI Head of Model & Behavior Policy Joanne Jang just published a blog post detailing how the company is approaching human-AI relationships and questions of AI consciousness.

The details:

• Jang said that people naturally anthropomorphize AI, a tendency amplified by models responding with what feels like non-judgmental empathy and validation.

• OpenAI considers AI consciousness currently unanswerable, instead focusing on how conscious it appears to users and its impact on mental wellbeing.

• The design philosophy is to thread a fine needle, aiming for a personality that is warm and helpful without giving it a fictional backstory, feelings, or desires.

• Jang also said that evolving human-AI relationships reflect both how people use the tech, but also “may shape how people relate to each other.”

Why it matters: AI labs are becoming the architects of digital companionship for millions of users, making choices that will shape societal norms around connection and empathy. This uncharted territory is essentially one big social experiment — and even the creators are uncertain about the psychological territory we are entering.

AI TRAINING

📚 How to turn complex research into quizzes

The Rundown: Google Gemini’s deep research feature can now analyze any topic in depth and automatically turn findings into interactive quizzes perfect for studying or teaching.

Step-by-step:

1. Visit Google’s Gemini website and click “Deep Research” at the bottom of the chat interface

2. Enter your educational topic with specific requirements (grade level, focus areas), and review and edit the research plan as needed

3. Let Gemini generate a comprehensive report from multiple sources (takes a few minutes)

4. Click “Create Quiz” to automatically generate an interactive quiz with multiple question types

Pro tip: The quiz will provide you with explanations after you answer either correct or incorrectly, review them after your mistakes to learn faster.

PRESENTED BY RUNNER H

🚨 Your job just got 1000x easier

The Rundown: Runner H is the newest AI agent you can delegate all your boring, repetitive, and time-consuming tasks to! Give it access to your tools, and it can handle entire workflows from a single prompt.

Some tasks you can delegate to Runner H include:

• Reading your important emails and drafting (or even sending!) replies

• Creating a Google Sheet with trending ad ideas and sharing it with your team on Slack

• Finding job opportunities and applying for you

Watch this video to see Runner H in action, before trying it for free to experience an agent that transforms the way you work!

AI RESEARCH

📜 AI reveals Dead Sea Scrolls are a century older

The Rundown: Researchers just discovered that the Dead Sea Scrolls may be up to a full century older than previously estimated after training an AI system called Enoch to analyze ancient patterns and combining it with radiocarbon dating techniques.

The details:

• Enoch was trained by linking known radiocarbon dates of scroll fragments with handwriting styles, learning to associate visual patterns with time periods.

• The new dating pushes some biblical texts back to the time of their presumed authors, with some texts coming in at up to 2,300 years old.

• The AI method offers a non-destructive alternative to carbon dating, which requires cutting samples from the precious manuscripts.

Why it matters: Even fields like archeology are seeing transformations in the AI era — with pattern recognition abilities continuing to unlock new secrets from history (like deciphering the Herculaneum scrolls). With ancient texts stored across museums and libraries worldwide, there is still tons of knowledge waiting to be discovered.

QUICK HITS

🛠️ Trending AI Tools

• 🤖 Gemini 2.5 Pro - New update with improvements across benchmarks

• 🗣️ Eleven v3 - SOTA text-to-speech model with support for 70+ languages

• 👄 Bland TTS - New voice AI with enhanced realism and control

• 🎥 HunyuanVideo-Avatar - Create multi-character talking videos from audio

💼 AI Job Opportunities

• 🤝 The Rundown - Partnerships Manager

• 🎤 Parloa - Lead Product Trainer

• 📅 UiPath - Executive Assistant

• 🧱 OpenAI - Full Stack Engineer, Post Training

📰 Everything else in AI today

Apple researchers published a new study revealing that reasoning models hit a “scaling limitation” where they think less and perform worse as complexity increases.

Anthropic added national security heavyweight Richard Fontaine to its Long-Term Benefit Trust, deepening the company’s focus on navigating AI’s global risks.

OpenAI rolled out an update to its Advanced Voice Mode, featuring more natural, expressive speech and improved translation capabilities.

Anysphere released Cursor v1.0, with new features including a Background Agent for remote coding, BugBot for automatic PR review, and new memory capabilities.

Google launched Portraits, a Labs experiment allowing users to have personalized experiences with AI versions of experts based on their voice and knowledge base.

Higsfield AI introduced Higgsfield Speak, a new update enabling talking avatars with custom styles, scripts, and motion.

FutureHouse released ether0, an open-weights chemistry-focused reasoning model that significantly outperforms top models on scientific tasks.

COMMUNITY

🎥 Watch our last live workshop

Check out our last workshop with Dr. Alvaro Cintas, The Rundown’s AI professor. By the end of the workshop, you’ll confidently be able to incorporate Flux Kontext into your creative workflows for consistent, high-quality results.

Watch here. Not a member? Join The Rundown University on a 14-day free trial.

See you soon,

Rowan, Joey, Zach, Alvaro, and Jason—The Rundown’s editorial team