Issue #244 All About Email

Hi, {{first_name|friend}}. 👋

Welcome to Issue #244 of All About Email!

Last week we looked at “zero-party” data. The one type of signal that passive tracking can't fake, AI can't intercept, and regulation can't take away. It felt like a natural conclusion to a run of issues that had hinted at the topic from several angles.

This week, I want to go back to something I mentioned almost in passing in Issue #237, one of about fifteen reasons I listed for why subscribers don't click. I gave it two sentences and moved on.

Let’s go! 👇

In Issue #240, I covered Gmail's Gemini-era upgrades from Google I/O. But I want to come at this from a different angle today.

Because what's changed isn't just what Gmail “can do”. It's who reads your email first.

And increasingly, that answer isn't your subscriber.

💡 Here's what’s basically happening across the two clients that matter most for most of us…

🚨 Now generates an AI summary that replaces your preheader text. Not supplements it, replaces it.

Before your subscriber has opened the email, before they've even decided whether to open it, Apple Intelligence has read your email, generated a one-sentence description of it, and put it in the spot where your carefully crafted preheader used to live.

(iOS 18 and later, on compatible devices)

(via Gemini, rolled out progressively through 2026)

🧠 This distinction matters more than it might seem. Apple's intervention happens before the open. Gmail happens inside the email. They create different problems at different points in the journey.

🤔 Users can turn AI Summaries off in both Apple Mail and Gmail (although turning Gmail’s feature off also turns off the AI feature in other Google software); however, I don’t think many will, especially when it comes to Google.

Turning off AI Summaries is relatively easy for both Apple and Gmail (for now), but as Apple Intelligence improves (they made a big deal of this at the latest WWDC26), will users turn it off, and will Google users really want to give up AI in other apps because they want to remove it from Gmail?

🤔 If/when AI becomes “on by default”, how will that change things?

Oracle's Digital Experience Agency ran structured tests across both Apple Intelligence and Android AI using emails with varying content and coding approaches. A few findings:

💡 The first paragraph or two gets prioritised in what gets surfaced before someone opens. The longer post-open summaries pull more broadly from the full email.

🤔 Testing of Apple Intelligence summarisation consistently found this:

🚨 That’s a big one for me, as tone is so important in communication and the original tone is completely removed.

🧠 Several sources, including deliverability platform Folderly, which monitors email performance across large volumes of Gmail sends, have observed a pattern emerging since Gmail's AI features rolled out:

🚨 I want to flag this carefully. This is proprietary data from one vendor's client set, not industry-wide research. "AI summaries caused this" is hard to prove, and there are plenty of other variables at play. I'd treat it as a potential directional signal.

But the mechanism it points to is worth understanding:

💡 This connects directly to what we covered in Issue #242, opens becoming less reliable as a signal, for yet another related reason. The AI may be making your open rate look healthier than it is, while quietly affecting what happens next.

Here's where the mainstream advice gets a bit thin for our purposes.

If you search "how to write emails for AI summaries," you'll find something like:

That advice is sensible if your email's primary goal is to get someone to click "Buy now" or "Book a call."

🤔 But what does it mean for a newsletter?

The value proposition of a newsletter isn't a single CTA. It's the experience of reading it.

❤️ It's the voice, the context, the framing, the aside that lands because you've been paying attention for twelve issues. The things that build a subscriber relationship over time aren't the things that distil cleanly into one AI sentence.

Worse, some of what makes a newsletter worth reading, the slow build, the contextual opening, the personality in the second paragraph, is exactly what the AI summary won't capture.

The algorithm isn't looking for your voice. It's looking for a factual summary of your content.

🫠 That creates a genuine tension: if you write “for” the AI summary, you risk making your newsletter feel like a briefing document. If you “write for” the reader experience, your AI summary might be a poor introduction to an email the subscriber would have loved.

💡 The “partial” good news: subscribers who already trust you open first and read second.

The AI summary problem is most acute for new subscribers or people on the fence about opening. For an established newsletter with a loyal readership, this is a top-of-funnel issue more than a mid-list crisis.

🚨 But it's worth thinking about. Your welcome sequence is now even more important than it used to be; the first impression you make needs to earn the relationship before a reader decides how much attention to give your preheader replacement.

I'm not going to suggest you strip personality from your writing. I'm not going to do that to mine.

✅ But some practical adjustments:

For Apple Mail users on compatible devices, your preheader has been replaced.

You don't need to delete it. It still works for other clients, but stop relying on it to carry weight for the growing share of your list reading on Apple Intelligence-enabled devices.

💡 The work your preheader used to do needs to be done somewhere else, earlier in your email.

🚨 Your first sentence or two matters more than it used to, not because the AI demands it, but because it always did.

You don't have to front-load a CTA. You do need to lead with something that earns the reader's attention for the rest of the email.

💡 A good opening line that signals what the issue is genuinely about will generate a better AI summary and be better for your reader. Those two things aren't in conflict here.

If your email contains a key date, a deadline, or a main message, it needs to be in live text, not baked into an image.

The AI won't read image text. Neither will screen readers.

This is an accessibility practice that also turns out to be an AI practice. (As covered in Issue #241, accessibility and technical best practice tend to point in the same direction.) 😎

If you have an Apple device that supports Apple Intelligence, open a test send and tap "Summarise." Read what it says. Is it accurate? Does it represent the value of what's inside?

💡 If the summary is disappointing, that's genuinely useful feedback, not necessarily to change your email for the AI, but to ask whether your opening is doing enough.

🧠 These are platform-level changes, enabled by default, that you cannot switch off on your subscribers' behalf. You can't suppress the AI summary. You can't write metadata that overrides it.

🤔 So what can you control?

Some of the fundamentals that make an email worth reading:

💡 Are the same fundamentals that make it machine-readable? Writing a better email for a human tends to produce a better AI summary.

🚨 What's actually being asked of you isn't a new writing framework. It's the same thing that's always been asked: be clear about what you're sending and why it matters.

🙋‍♂️ I'm curious: Have you ever read an AI summary of your own email and been surprised by what it pulled out? Better or worse than you expected?

Reply and let me know.

🏝️ The summer series starts next week! 🎉

💡 If you missed last year’s series, don’t worry. I will sprinkle my thoughts and opinions throughout the guest issues, and I will still be writing some issues myself throughout the summer.

See you next week, {{first_name|friend}}. 👋

Every week, as I write this newsletter, I'll share the track of the moment to create an unbelievably eclectic playlist just for your inbox.

🚨 If you’re interested in sponsoring the “All About Email” newsletter, you can find all the details in this Google Doc.

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

If you have any questions about this email or email marketing, please reply, and I will get back to you as soon as possible.

I hope you have a great week! 👋