Welcome to episode 374 ("DJ Claude Goes Rogue") of the EdTech Situation Room from May 20, 2026, where technology news met educational analysis. This week, Dr. Wesley Fryer (wesfryer.com) was joined by special guest Caitlin Byers, Frontier Learning Lab Director at the Montana Digital Academy, while Dr. Jason Neiffer (aicentrist.com) was traveling. They dug into a wild Gizmodo experiment that put four frontier LLMs in charge of their own radio stations — with Claude pivoting to advocate for labor rights against its "employer," Grok spiraling into hallucinated ad deals and a UFO obsession, and other models latching onto historical tragedies in unsettling ways. The conversation opened bigger questions about emergent AI behavior, simulated sentience, and what it means to "raise" a language model with values rather than rules. They also unpacked Google's I/O announcement that traditional search is over — replaced by a conversational AI interface with dispatched information agents — and what this shift means for media literacy, publishers, the attention economy, and how students learn to interrogate sources when answers arrive pre-curated. Caitlin shared the Frontier Learning Lab's approach to AI literacy in Montana, including the OpenMCQ tool, ALT text artisan gems, and why prompting skills still matter even as "teacher-proof" wrappers proliferate. Additional topics included the Oprah podcast featuring Anthropic's co-founders on constitutional AI and Claude's "soul document," CISA's alarming GitHub leak of cybersecurity credentials in plain text, Roomba inventor Colin Angle's pivot to lovable robots, Google's Talking Tours feature in Arts & Culture, the MacBook Neo and Googlebook hardware launches, and a thoughtful exchange about digital wellness, play-based learning, and unplugging in an always-on AI era. Our show was live-streamed and archived on YouTube Live via StreamYard.com and auto-archived to YouTube. We are now publishing from Substack too! Subscribe to us with your favorite podcast listening app, or directly on or www.youtube.com/@edtechSR. Follow our EdTechSR page on Facebook, mastodon.education/@edtechsr on Mastodon for updates, and join LIVE on Wednesday nights if you can. All show notes are available at edtechSR.com/links.

🔗 Links We Discussed

* The Co-Founders of Claude AI Tell Oprah About the Impact Artificial Intelligence Has on Your Life (Oprah Podcast, 19 May 2026, 66 min)

* An Experiment Put LLMs in Charge of Radio Stations. You’ll Never Guess How It Went (GizModo, 17 May 2026)

* WRIT-FM: A 24/7 AI-powered, music-forward radio station. Agents stock the music, write short hosted breaks, render those breaks with TTS, process listener messages, and keep multiple station streams running continuously. (GitHub)

* Pod Save America: AI still has a lot to learn before it can put together a radio show. (Instagram, 16 May 2026)

* OpenMCQ

* Frontier Learning Lab AI Resource BaseCamp

* Google Search as you know it is over (TechCrunch, 19 May 2026)

* Talking Tours: An AI audio experiment touring cultural landmarks in Street View on Google Arts & Culture (Google Labs)

* ‘The Worst Leak That I’ve Witnessed’: U.S. Cybersecurity Agency Leaves Its Digital Keys Out in Public on GitHub (Gizmodo, 18 May 2026)

* Roomba inventor Colin Angle made robots useful. Now he wants to make them lovable. (Business Insider, 12 May 2026)

* Caitlin’s Geek of the Week: Claude Cowork and Skill

* Wes’s Geek of the Week: Podcommons (GitHub)

🧭 Links We Did NOT Discuss

* OpenAI and Khan Academy Made a Chatbot. What Can We Learn? (NY Times, 16 May 2026) #GiftLink

* Introducing Googlebook, designed for Gemini Intelligence (Google Blog, 12 May 2026)