Issue #188 All About Email

Hi, friend. 👋

Welcome to Issue #188 of All About Email!

Last week, I made a massive announcement (for me anyway 🤣) and added a little further note about Gmail clipping.

This week, Microsoft starts (today) enforcing their new sender guidelines, there’s a new AI native email for Gmail, and I launch a new newsletter feature.

Let’s go! 👇

Outlook Sender Guidelines

🚨 This time, it’s a little bit different as Microsoft’s new sender guidelines come into force.

If you are new to this newsletter, then we’ve been here before, and these are important in light of Microsoft’s enforcement starting today:

• Issue #168 - Breaking down the basics of deliverability.

• Issue #169 - Subdomains and deliverability

The very first email I sent from Beehiiv was about the Google and Yahoo Sender Guidelines, and if you’ve been following those, you should be fine.

⚠️ However, if your domain is NOT authenticated and you are a bulk sender (5,000+ emails), you are going straight into spam from today.

Al Iverson of Valimail breaks everything down nicely in this short video. 👇

🚨 There are also some additional considerations with Microsoft. 👇

Additional Email Hygiene Recommendations

Large senders should also adopt these practices to maintain quality and trust:

• Compliant P2 (Primary) Sender Addresses: Ensure the “From” or “Reply‐To” address is valid, reflects the true sending domain, and can receive replies. 

• Functional Unsubscribe Links: Provide an easy, clearly visible way for recipients to opt out of further messages, particularly for marketing or bulk mail. 

• List Hygiene & Bounce Management: Remove invalid addresses regularly to reduce spam complaints, bounces, and wasted messages. 

• Transparent Mailing Practices: Use accurate subject lines, avoid deceptive headers, and ensure your recipients have consented to receive your messages. 

⚠️ That first bullet point (Compliant P2 (Primary) Sender Addresses), friend, is very important, as Google, Yahoo, and Apple haven’t requested this (yet).

And here’s an important comment from Microsoft about its guidelines, including the above considerations. 👇

What Should I Do?

✅ As I said at the start of this email, if you’ve been following best practices and sender guidelines set out by other mailbox providers over the last year,

⚡️ You might need to change your “reply-to” address if it’s not a real mailbox (i.e. it can send and receive email), although we don’t know when/how that will be enforced.

🧠 If you are still confused, check out this fantastic deep dive from Valimail with everything you need to know.

💡 Also, check out breakdowns from Alison Gootee and Lauren Meyer.

Before You Go

There’s another new Gmail replacement in town!

Yes, friend, AI is involved, but it’s not the same as the new Notion Mail, which we covered back in Issue #180.

This time it’s called Zero Mail and it’s:

• Open Source native AI

• Serverless with the power of Cloudflare.

• Option to self-host (even more privacy)

I’ve already connected with my Gmail account to check it out, and I hope to test the self-hosted version soon.

🫠 Once you connect your Gmail account to Zero Mail, there is no onboarding, and you are thrown into the deep end (unlike Notion Mail, which has wonderful onboarding), and to be honest, I was a bit clueless.

I imagine in the future, onboarding will be added, and more to come on this in the next few weeks.

🎉 New Feature - Powered By Music!

I listen to a lot of music, friend, especially when writing newsletters.

My tastes are eclectic, and when I hit the publish (schedule) button each week, I’ll share the track I’m listening to and build the craziest playlist you’ve probably ever seen.

Starting with a blast from the past and my kids’ “go-to” for starting a car journey. 🤣

Sponsorship Opportunities

🚨 If you’re interested in sponsoring the “All About Email” newsletter, you can find all the details in this Google Doc. I currently have “Classified” slots and a Main Sponsor slot available.

That’s It For This Week 👋

⏭️ Next week, (if I’ve had time), I will be taking a closer look at Zero Mail (not the self-hosted version, that will take a little bit longer).

I’ll also have a little update on my new email community, “Campfire”.

See you next week!

Email Marketing News & Tips

This week's excellent and insightful email news & tips:

• May the 4th - Now this is how to theme a newsletter for Star Wars Day. (Action Rocket)

• Gen Z at Work - How They Use Email – And What Makes Them Happy in Their Careers. (ZeroBounce)

• Don’t Forget Apple - Postmaster information for iCloud Mail. (Apple)

• I Did It! 🙌 - and it took me less than 2 minutes. Quick research survey. (Jenna Tiffany & EmailTooltester)

• Redesigned - Robust but simple, revamped automations with a customer focus. (Natalie Lynch & Mailjet)

• Designed vs Text Emails - What Really Works in Email Marketing?. (Naomi West & Really Good Emails)

• Should Email Follow? - Is intent-based unsubscribe the future of email marketing? (Sebastian Kuemmel)

• Clever Idea - He added 5,000+ subscribers with one simple tweak. (Chenell Basilio)

• Legal Compliance - Why accessibility in email isn’t optional anymore. (Megan Boshuyzen & Mailgun)

• Personalisation - Dynamic Images, Alt Text, and Accessibility. (Sarah Gallardo)

• 2025 Fresh Data -How many emails are sent per day? (EmailTooltester)

• Email Courses - How to Repackage Your Best Content Into Email Courses That Grow Your List and Convert Readers. (Inbox Collective)

If you have a question about this email or email marketing, reply, and I will answer you as soon as possible.

I hope you have a great week! 👋