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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