This Episode We Cover:

🔥 Major Industry Moves


Notion Acquires Skiff - The privacy-focused email provider with nearly 2M users gets absorbed and shut down


12-month sunset period for manual data migration
What this means for the future of privacy-focused email services
Expected bounce rate increases from @skiff.com addresses




🤖 AI in Email: Promise vs Reality


Zero Email Client - New AI-native approach to inbox management


Thread summarization and AI-powered drafting features
Smart categorization to reduce email time
The social media algorithm concern: Are we heading toward filtered inboxes?


Anti-Phishing AI Failures - Lessons from Yahoo's LLM experiment

How AI protection "failed within an hour" in production
Bad actors adapting faster than models can learn
The ongoing cat-and-mouse game in email security




🔐 Authentication & Security Updates


DMARC Enforcement Momentum - Google and Yahoo leading the charge


Smaller providers like Orange and Seznam following suit
Czech Republic hitting 90% DMARC adoption
Push for policies to shift from "none" to "quarantine"
Real impact: "Basic abuse without authentication has almost disappeared"




⚠️ Service Disruptions & Changes


Rackspace Email Issues - Recurring delivery problems


IP blocks from SpamCop and Microsoft (April 11 & May 27, 2025)
Ongoing compliance challenges for the hosting giant


Microsoft Cuts Nonprofit Support - Abrupt end to free Office grants

Nonprofits left scrambling for alternatives




Key Takeaways:


AI in email is promising but faces real-world adaptation challenges
Authentication enforcement is working, but requires industry-wide adoption
Acquisitions in the email space often mean service shutdowns—plan accordingly
Infrastructure providers still struggle with deliverability compliance


Mentioned Companies/Services:


Notion, Skiff, Zero, Yahoo, Google, Orange, Seznam, Rackspace, Microsoft
SpamCop, DMARC, LLM anti-phishing


 

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