This Episode We Cover:
Notion Acquires Skiff - The privacy-focused email provider with nearly 2M users gets absorbed and shut down12-month sunset period for manual data migrationWhat this means for the future of privacy-focused email servicesExpected bounce rate increases from @skiff.com addresses🤖 AI in Email: Promise vs Reality
Zero Email Client - New AI-native approach to inbox managementThread summarization and AI-powered drafting featuresSmart categorization to reduce email timeThe social media algorithm concern: Are we heading toward filtered inboxes?Anti-Phishing AI Failures - Lessons from Yahoo's LLM experimentHow AI protection "failed within an hour" in productionBad actors adapting faster than models can learnThe ongoing cat-and-mouse game in email security🔐 Authentication & Security Updates
DMARC Enforcement Momentum - Google and Yahoo leading the chargeSmaller providers like Orange and Seznam following suitCzech Republic hitting 90% DMARC adoptionPush 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 problemsIP blocks from SpamCop and Microsoft (April 11 & May 27, 2025)Ongoing compliance challenges for the hosting giantMicrosoft Cuts Nonprofit Support - Abrupt end to free Office grantsNonprofits left scrambling for alternativesKey Takeaways:
AI in email is promising but faces real-world adaptation challengesAuthentication enforcement is working, but requires industry-wide adoptionAcquisitions in the email space often mean service shutdowns—plan accordinglyInfrastructure providers still struggle with deliverability complianceMentioned Companies/Services:
Notion, Skiff, Zero, Yahoo, Google, Orange, Seznam, Rackspace, MicrosoftSpamCop, DMARC, LLM anti-phishingGot thoughts on this episode? Hit us up at [email protected]
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