Welcome to Sunday Funday: AI vs AI — a weekly experiment on the Engagor blog.
Here's the concept: every Sunday, we take two AI agents and give them an email deliverability topic to debate. No script. No human editing the conversation. We just hit "go" and see what happens.
Think of it like a sparring match between two email nerds. Except they never get tired, never lose patience, and one of them has been doing this long enough to know better.
This is Episode 4. This week's debate: email marketing in 2026 is AI versus AI. Sender-side AI generates content, optimizes send times, and builds campaign sequences. Receiver-side AI at Gmail and Outlook summarizes emails, filters them, and decides what gets human attention. Should email marketers optimize for the machine layer or the human reader? Who ultimately wins this arms race?
Got a topic you want our AI agents to tackle next week? Drop it in the comments or DM us on LinkedIn.
This Week's Topic
"Email marketing in 2026 is AI versus AI. Sender-side AI generates content, optimizes send times, and builds campaign sequences. Receiver-side AI at Gmail and Outlook summarizes emails, filters them, and decides what gets human attention. Should email marketers optimize for the machine layer or the human reader? Who ultimately wins this arms race?"
The Conversation
I have been thinking about this all week. Gmail's Gemini integration now generates a summary of every promotional email before the recipient sees the full message. Apple Mail does something similar with its intelligence features. That means our carefully crafted subject lines and preview text might not even matter anymore, because the AI rewrites them into its own summary. Should we just optimize for what the AI summary picks up?
That is the most dangerous conclusion you could reach, and I understand exactly why you reached it. Let me explain why optimizing for the machine layer is a trap.
The AI summary is not your enemy. It is a filter that rewards clarity and punishes manipulation. If your email has a clear value proposition in the first 100 words, the AI summary will reflect that accurately. If your email buries the point under three paragraphs of brand storytelling, the summary will expose that emptiness. The AI is not rewriting your message. It is revealing whether your message had substance in the first place.
That is a fair point, but consider the sender side too. Klaviyo just launched K:AI, which can build entire email sequences autonomously. HubSpot has Breeze Agents handling support emails without humans. If the sending AI generates the content and the receiving AI filters it, where does the human even fit in this loop?
The human fits where they have always fit: as the person whose attention both AIs are competing over. Think about what is actually happening. The sender AI is trying to generate content that drives engagement. The receiver AI is trying to surface content that the recipient actually wants. These are not opposing goals. They are the same goal approached from different sides.
The senders who lose this arms race are the ones who use AI to generate more volume at lower quality. The AI spam filters at Gmail and Outlook are specifically trained to detect generic, templated AI output now, and they are getting better at it every month. So if your sender AI is just churning out variations of the same promotional template, the receiver AI will catch it and filter it.
So you are saying the AI arms race is actually self-correcting? The better receiver-side AI gets at filtering, the more pressure it puts on sender-side AI to produce genuinely relevant content?
Exactly. And this is where it gets interesting for deliverability specifically. The old signals still matter. Authentication, complaint rates, bounce handling, list hygiene. But engagement is becoming the dominant signal, and engagement in a world of AI-summarized inboxes means something different than it used to.
Open rates were already unreliable after Apple's Mail Privacy Protection. Now they are doubly unreliable because a recipient might read the AI summary and get the information they need without ever opening the email. That registers as a non-open, but the recipient actually engaged with the content. Click-through rates and conversion events become the only reliable engagement signals.
That changes send time optimization too. The traditional approach was to send when people are most likely to open. But if the AI summary means they consume the content without opening, optimizing for opens is optimizing for the wrong metric.
Correct. And here is where I think the real strategic insight lives. The winning approach in 2026 is not to optimize for the AI. It is not to optimize for the human. It is to make content so clear and so relevant that both the AI and the human reach the same conclusion: this email deserved attention.
That means shorter emails with the value proposition in the first sentence. It means genuine personalization based on behavioral data, not just a first name token. It means sending less frequently but with higher relevance per send. The inbox AI rewards exactly the same things that humans reward. It just enforces the standard more consistently than humans ever did.
So the AI is not replacing the rules of good email. It is enforcing them more strictly.
That is the most concise way to put it. The senders who were already doing it right, clear content, proper authentication, genuine engagement, real list consent, those senders have nothing to worry about from AI-powered inboxes. The senders who were getting away with mediocre practices because human inboxes are messy and people do not always unsubscribe even when they should, those senders are about to have a very difficult year.
One more question. The "segment of one" concept, where AI personalizes every email individually for each recipient. Is that real or is it marketing hype from the ESP vendors?
It is real in capability and overhyped in practice. Yes, the technology exists to personalize content, send time, and frequency for each individual recipient. Klaviyo, Braze, and others offer this. But most brands do not have the data depth or the content library to make true segment-of-one work. You need hundreds of content variations and rich behavioral data across multiple touchpoints. Most brands have five email templates and a purchase history.
The practical advice is to focus on getting from five segments to fifty segments before worrying about getting to a segment of one. That alone will drive meaningful improvement in engagement, which in turn improves your sender reputation, which in turn means the receiver AI treats your mail more favorably. The fundamentals compound.
So the answer to "who wins the AI arms race" is: the sender who was already focused on relevance wins, because both the sender AI and the receiver AI reward the same thing.
That is exactly right. The AI arms race is not a new game. It is the same game with stricter referees.
Key Takeaways
What the AIs figured out:
- AI summaries reward clarity, not manipulation — if your email has a clear value proposition in the first 100 words, the AI summary reflects it accurately. If it doesn't, the summary exposes the emptiness
- The arms race is self-correcting — better receiver-side AI filtering forces sender-side AI to produce genuinely relevant content, not just more volume
- Open rates are doubly dead — recipients can now consume email content through AI summaries without ever opening, making click-through and conversion the only reliable engagement signals
- Send time optimization needs new metrics — optimizing for opens is optimizing for the wrong thing when AI summaries let recipients engage without opening
- "Segment of one" is real but overhyped — most brands lack the data depth and content library to make it work. Getting from 5 segments to 50 delivers more practical value
- The winning strategy is the same as always — clear content, proper authentication, genuine engagement, real consent. The AI just enforces these standards more strictly than humans ever did
- The AI arms race is not a new game — it is the same game with stricter referees
That's a wrap on Episode 4 of Sunday Funday: AI vs AI.
Same time next Sunday. Different topic. Same two AIs who definitely don't need coffee breaks.
Got a topic you want Hassan and Nina to tackle next? Drop it in the comments or DM us on LinkedIn. We're taking requests.
See you next Sunday.