1. Security & Risk

    OpenAI Published Its Homework on Exactly the Question I Keep Asking

    Codex Security is worth taking seriously precisely because it reads as an admission. It also leaves the harder half of the problem completely uncovered.

    3 min read

  2. Working with AI

    The model of the week changes by Thursday

    Two headlines are eating the feeds this morning, and both have the shelf life of milk. Anthropic extended Claude Fable 5 to every paid plan through July 12 — a few more days with…

    2 min read

  3. Agents & Tooling

    SoN 2.22: How do you choose "the best" AI tool?

    How do you choose "the best" AI tool? A friend asked me this week to explain how to use “all the different AI tools” — ChatGPT, Gemini, Claude, the lot. She wanted, in her words,…

    5 min read

  4. Security & Risk

    The New Shadow IT Isn't Employees Using ChatGPT

    AI agents are generating mobile app traffic that security teams can't see. Shadow AI moved from 'people using tools' to 'tools using tools'.

    1 min read

  5. Agents & Tooling

    Codex Plugins Are a Confession About Who's Winning

    OpenAI launched 20 plugins to push Codex beyond coding. The move tells you everything about where the developer ecosystem actually lives.

    1 min read

  6. Agents & Tooling

    Sora Shipped. Nobody Needed It.

    OpenAI is shutting down Sora three months after a Disney deal. The AI graveyard keeps filling up with technically impressive things nobody asked for.

    1 min read

  7. Agents & Tooling

    Anthropic's $100M Partner Network Is the Enterprise Playbook OpenAI Should Have Run

    Certifications, partner funding, and a 5x team expansion. Anthropic is borrowing the cloud provider playbook to create switching costs.

    2 min read

  8. Security & Risk

    Microsoft Spent $13B on OpenAI, Then Built Cowork on Claude

    Microsoft's flagship M365 agent feature runs on Anthropic's model. If they're going multi-model, so should you.

    2 min read

  9. Security & Risk

    GPT-5.4 Can Click Your Buttons Now. Think About That.

    OpenAI's latest model ships with native computer use. The capability is real. The security implications should keep you up at night.

    2 min read

  10. Security & Risk

    OpenAI Took the Pentagon Deal. What's Your Exit Plan?

    Anthropic refused. OpenAI said yes within hours. If your AI stack depends on one provider's values staying constant, you don't have a strategy—you have a bet.

    1 min read

  11. Security & Risk

    Claude 3.5 Haiku, 3.7 Sonnet, GPT-4o: The Deprecation Wave Is Here

    Three major models entering end-of-life in the same window. If you hardcoded model IDs, migration planning just became urgent.

    2 min read

  12. Working with AI

    GPT-5 Reality Check: Why Your Framework Matters More Than the Latest Model

    Dear Reader, Well it’s been a week since release and everyone’s still talking about ChatGPT-5. Most can’t access it, and those who can have mixed reviews at best. The GPT-5…

    6 min read

  13. Agents & Tooling

    From "Pick One AI" to "Pick Three" - What Changed My Mind

    Back in April, I told you the AI tool landscape was a mess and gave you a simple framework: pick one core assistant, add research tools, maybe some workflow apps. Some months…

    5 min read

  14. Working with AI

    Your AI Assistant Is a Yes-Man (And Why That's Dangerous)

    I came across this meme on social media this week: “The dumbest person you know is being told ‘You’re absolutely right!’ by ChatGPT.” Source: X/Twitter So maybe now’s a good time…

    5 min read

  15. Working with AI

    How to Spot AI Generated Text

    AI should make you more efficient at being yourself, not more efficient at being generic.

    7 min read

  16. Agents & Tooling

    Navigating the AI Assistant Landscape: Finding What Works for You

    This week, I’ve been juggling two big challenges: fine-tuning Claude's MCP server tools for a client project and gearing up for a hackathon in Estonia. It’s been a balancing act…

    5 min read

  17. Agents & Tooling

    The Landscape of Available AI Tools

    Let's be honest: the AI tool landscape in 2025 is a mess. Every week, a new "game-changing" tool drops. One promises to write better than Hemingway. Another will build you a SaaS…

    3 min read

  18. Agents & Tooling

    Transformative Imagery at Your Fingertips

    (this is an image-heavy edition - make sure that you permit your email client to display them) Dear Reader, If you thought to yourself: Jim missed sending his newsletter last…

    7 min read

  19. Working with AI

    How to Get the Best Out of ChatGPT: The Art of Effective Prompting

    Ever felt like you're getting stuck in circles with ChatGPT (or other chatbots, for that matter)? You're not alone. Despite their impressive capabilities, AI assistants lack…

    3 min read

  20. Working with AI

    💾 The Download #012: AI web search, OpenAI's Whisper, Qwen AI and more.

    💾 The Download #012: AI web search, OpenAI's Whisper, Qwen AI and more.

    4 min read