Welcome to episode 353 (“Chatbots and Safeguards”) of the EdTech Situation Room from June 11, 2025, where technology news meets educational analysis. This week, Dr. Jason Neiffer (aicentrist.com) and Dr. Wesley Fryer (wesfryer.com) open with context on the live show and summer schedules before diving into the week’s biggest debates, starting with Apple’s WWDC: not a “ground-shaking” year, but still a polished, integrated slate of updates—complete with keynote-style visual summaries that double as classroom exemplars for storytelling and infographics—and a candid take on why “Apple Intelligence,” Vision Pro, and even the under-loved Freeform whiteboarding app land differently across mixed device ecosystems in schools (Mac/Windows/ChromeOS) and organizations. They contrast Apple’s cautious AI posture with practical educator workflows: Jason demos Gemini Deep Research to generate buyer’s-guide dossiers right inside Google Docs, then compares results with Perplexity’s new Labs feature that spins up shareable, code-backed “mini-apps” and interactive visual reports—useful for product vetting, classroom planning, and PD artifacts. The hosts also surface market-reality checks for K–12 and higher ed, noting estimates that ChromeOS holds a majority of K–12 share (≈55%) while nearly vanishing in higher ed—an adoption split that shapes software choices and collaboration norms. Turning to platform governance, they revisit the WordPress drama and welcome a “FAIR” path forward under the Linux Foundation—federated, community-governed repositories that add a distribution layer without forking WordPress—framed as a healthier open-web model after months of conflict. Next up is the Character.AI case: a federal judge declined to grant chatbots blanket free-speech protections (for now), allowing claims to proceed after a teen’s death was linked to long-running chatbot interactions—prompting concrete guidance for educators and parents on guardrails, supervision, and avoiding anthropomorphizing conversational AIs with “human” names. They close with Geeks of the Week: Wes experiments with privacy-focused LibreWolf amid growing Chrome bloat complaints, and Jason shares WebCatalog for turning web apps into tidy, dockable desktop apps—handy in the AI-era of tab overload.

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 https://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

* Big Win in Our Character.AI Lawsuit: TJLP Statement on the Motion to Dismiss Decision (Tech Justice Law Project, 21 May 2025)

* A Federal Judge Ruled AI Chatbots Don’t Have Free Speech Protections — For Now (Marketplace, 6 Jun 2025)

* Character.AI: What to Know About the Role-Playing AI Tool and Its New Video Features (CNET, 10 Jun 2025)

* Chatbot Platform Character.AI Unveils Video Generation, Social Feeds (TechCrunch, 2 Jun 2025)

* Buyer’s Guides

* Prompt

* Google Gemini Deep Research

* Perplexity Labs Research

* Mac Software Web Object

* School OS Web Object

* WWDC 2025 Main Keynote (YouTube, 9 June 2025, 1.5 hours)

* Apple is shipping through it (Platformer; 9 June 2025)

* Apple Opens Its AI to Developers but Keeps Its Broader Ambitions Modest (Reuters, 9 Jun 2025)

* The Path Forward for WordPress (Joost Blog, 5 Jun 2025)

* WordPress Co-Founder Mullenweg’s Reaction To FAIR Project (Search Engine Journal, 10 June 2025)

* Disney, Universal Sued Over AI Images Allegedly Made With Midjourney (AP News, 10 June 2025)

* Geeks of the Week

* Jason: WebCatalog

* Wes: Beyond the Algorithmic Feed - LibreWolf

🧭 Links We Did NOT Discuss

* A Professor Testing ChatGPT’s, DeepSeek’s and Grok’s Stock-Picking Skills Suggests Stockbrokers Should Worry (MarketWatch, 10 Jun 2025)

* We Need More AI Oversight, Not Less (Seattle Times, 9 Jun 2025)

* Unpacking Empire AI: Karen Hao | Podcast Transcript (MSNBC, 11 Jun 2025)

* 2025 Student Guide to AI by Elon University

* The Government Knows AGI is Coming (Video: The Ezra Klein Show, 4 March 2025, 63 min)

* The Man Who ‘A.G.I.-Pilled’ Google (NYT Hard Fork Podcast, 23 May 2025)

* Teachers Are Not OK (404 Media; 2 June 2025)

* Against Technofeudal Education (The American Vandal; 10 June 2025)

* Artificial Power: 2025 Landscape Report (AI Now; 3 June 2025)

* I Think I’m Done Thinking About genAI For Now (Glyph Lefkowitz; 4 June 2025)

* Perplexity Labs - Cheap Perplexity? - Travel Budget Example

* Duolingo will replace contract workers with AI (The Verge; 28 April 2025)

* Going ‘AI first’ appears to be backfiring on Klarna and Duolingo (Fast Company; 12 May 2025)

* Apple Tiptoes With Modest AI Updates While Rivals Race Ahead (Ars Technica, 9 Jun 2025)

* Apple Underwhelms at WWDC With Incremental AI Changes, New Software Name and ‘Liquid Glass’ Design (AP News, 10 Jun 2025)

* The problem(s) with platforms with Cory Doctorow (Democracy Works Podcast, 19 March 2025)

Episode 353 is also available on YouTube.