May 29 what happened this week in the world of email and emailexpert

Inbox Intel: from emailexpert

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https://emailexpert.com Launched: May 28, 2025
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Inbox Intel: from emailexpert
May 29 what happened this week in the world of email and emailexpert
May 28, 2025, Season 1, Episode 3
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Episode Summary

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

 

Got thoughts on this episode? Hit us up at [email protected]

Want the inside track on what we're building at emailexpert? Check out our membership options and join the conversation.

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Inbox Intel: from emailexpert
May 29 what happened this week in the world of email and emailexpert
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00:00:00 |

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

 

Got thoughts on this episode? Hit us up at [email protected]

Want the inside track on what we're building at emailexpert? Check out our membership options and join the conversation.

This week on Inbox Intel, we dive into the stories shaking up the email world—and what they mean for all of us in the trenches.

We break down Notion's acquisition of Skiff and the messy aftermath that left nearly 2 million users scrambling to export their data before shutdown. Plus, we examine Zero, the new AI-native email client promising to revolutionize inbox management with thread summarization and smart categorization—but are we ready for algorithms controlling our inboxes like social media feeds?

On the security front, we explore the harsh reality of AI in anti-phishing efforts, where Yahoo's LLM-based protection "failed within an hour" as bad actors adapted faster than the models could learn. We also cover the ongoing DMARC enforcement push from Google and Yahoo, and why smaller providers like Orange and Seznam are following their lead—with some impressive results.

Finally, we touch on Rackspace's recurring email delivery nightmares and Microsoft's abrupt end to free Office grants that's left nonprofits in the lurch.

As always, no fluff—just the real talk on what's actually happening in email, from our perspective at emailexpert and beyond.

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