AI in email marketing has been a topic of discussion for years. But in the past few months, it’s truly exploded—just in time for Black Friday.
Black Friday is already a chaotic battle for attention in crowded inboxes. Now, with developments like AI summaries, Yahoo’s new “catch up” feature, AI assistants, and potential misrepresentation on the horizon, understanding how AI impacts your emails is more critical than ever.
Today we’re digging into these recent developments and how marketers can adapt to ensure their Black Friday emails stand out—even to the robot middlemen.
AI summaries are here—whether we want them or not
Of course, we’d love subscribers to be head-over-heels engaged with every inch of our copy and design. However, mailbox providers are adapting their user experiences to accommodate shrinking attention spans.
This began with Gmail annotations. As we noted in our previous post about Gmail annotations, these snippets of code are useful for skimming but prone to errors when not sender-asserted. Despite these challenges, Gmail’s interest in AI is aligned with the rest of the world and continues to innovate frenetically. They have recently allowed collaboration with Google Gemini in Gmail for summarizing and drafting features, but to use it, you need an eligible Google Workspace or Google AI plan. Gmail has also introduced another form of AI summation: Deal Cards. This feature summarizes your email and creates a card with your sale or offer to be displayed in the promotions tab.
Yahoo took the summary trend a step further with its new “catch up” feature, which offers users AI-powered recaps of their unread emails. These summaries make it easier for subscribers to decide whether to keep or delete a message. The goal is to help users declutter inboxes, especially after a Pollfish survey revealed that many Millennials and Gen Zs were missing time-sensitive appointments due to email overload. Yahoo has even gamified the experience, rewarding users with confetti and celebratory animations when they reach inbox zero.
With these features generating excitement, email marketers must pay close attention to how their emails are skimmed and summarized by AI. All the personalization touchpoints marketers are implementing in their segmentation efforts based on subscriber demographics, purchase behavior, and engagement could be boiled down to a few core points, effectively losing many of the subtleties and nuances senders worked so hard on.
And this is just the beginning of what’s to come—mailbox providers aren’t the only ones bringing AI into the inbox…
Perplexity’s AI inbox assistant
Perplexity, an artificial intelligence company known for its search engine that delivers answers with source citations, recently unveiled its new AI-powered “Email Assistant”—a tool designed to streamline inbox efficiency.
This advanced agent can schedule meetings, draft replies, mark emails as needing a response or simply as “FYI,” and deliver personalized summaries and priorities. Currently compatible with both Outlook and Gmail, the service promises impressive efficiency gains of anywhere between 3x to 18x. Even with its hefty price tag, it’s clear the industry wants to cater to the faster pace, greater automation, and a relentless push for efficiency. For consumers, these developments sound like a dream. Imagine having an AI that manages your inbox without lifting a finger!
But for email marketers, there’s another side to the story: if AI-generated emails are being summarized and responded to by AI assistants, humans could be completely removed from the email experience, potentially causing a significant decline in traditional email marketing metrics.
Unfortunately, lower engagement signals are only one of the hurdles marketers will have to clear. The other might need to get lawyers involved…
Misrepresentation and potential legal issues
AI may be fancy but it’s not immune to mistakes! While it’s tempting to blame the technology, errors in AI-generated summaries could lead to confusion or even legal consequences. For example, misleading human-created subject lines have previously resulted in lawsuits and costly fines for companies, demonstrating the serious implications of misrepresentation.
Now, consider a more complex scenario: What if your subject line and email content are accurate, but an AI misinterprets them and produces an incorrect summary? Who is liable for the resulting confusion? Could the sender be held accountable by the customer, or could the email service provider (ESP) be liable to the sender? Could this lead to a new wave of potential legal cases? Early examples of such disputes are already emerging.
So, what does this mean for email marketers? How can you safeguard your brand, protect your audience’s trust, and avoid potential legal battles in the age of AI-driven inboxes?
How to fight back ahead of Black Friday
On a recent episode of the Email After Hours podcast, Guy Hanson and Danielle Gallant shared valuable insights on how email marketers can adapt to AI changes just in time for Black Friday.
As they discuss in the episode, this situation isn’t hopeless! Email marketers have several tools at their disposal to stay ahead of the curve. Here are a few more actions to take into your own hands:
- Make your emails more machine-readable: Using semantic HTML, text-based copy, and following best practices for creating accessible emails will make it easier for AI to interpret your messages. Think about your email content the same way you think about optimizing web content for SEO: What kind of content is the AI summary likely to identify? How can you make your main points crystal clear?
- Avoid all-image emails: On the flip side of the point above, AI features can’t interpret information embedded in images. Stay away from them!
- Let subscribers opt down or snooze: With AI making it easier for users to opt out entirely, get ahead by empowering subscribers to choose how often they hear from you. Offering options to reduce frequency or temporarily pause emails can preserve engagement without losing them completely.
- Implement annotations: If you have the dev resources, coding Gmail-approved annotations can help ensure your emails are summarized correctly. If you can’t beat the AI, join it!
- Repurpose open rates: After Apple MPP, email marketers moved away from open rates as a true engagement signal. But with the AI features swirling around the inbox, opens can be a good proxy for open trends because the pixel fires only happen if the messages landed in the inbox.
- Don’t be misleading: Misleading subject lines or content erode trust and could land you in legal trouble. Ensure your messaging is clear, accurate, and optimized to minimize misinterpretation by AI.
- Leverage BIMI: With AI-driven inboxes rife with misinformation and spoofing, BIMI (Brand Indicators for Message Identification) can help your brand logo stand out and establish credibility. With options like Common Mark Certificates (CMCs) and Apple Branded Mail, even small businesses can benefit.
Preparing for industry shifts and Black Friday
AI is transforming the email marketing landscape—from how inboxes are organized to how messages are interpreted. As these tools evolve, marketers face exciting opportunities but also significant risks, including lower engagement and potential legal pitfalls. By implementing strategies like semantic HTML, annotations, and BIMI, you can stay ahead of the curve and ensure your emails thrive in this new AI-driven era AND peak sales season.
We hope this is a helpful place to start getting ready for Black Friday chaos.
Want to dive deeper into email optimization? Check out the Litmus from Validity’s 2025 State of Email report for a full breakdown of the email marketing landscape and insights on how marketers everywhere are becoming better senders.