Mailbox Provider AI: Automatic Extraction and Email Previews


April 08, 2025
Written by
Reviewed by
Denis O'Sullivan
Contributor
Opinions expressed by Twilio contributors are their own

Mailbox Provider AI: Automatic Extraction and Email Previews

In today’s attention economy, navigating your email inbox can be overwhelming. The sheer volume of unread messages means you don’t have time to carefully sift through all of them. But what if you’re missing out on content you’d actually benefit from seeing? AI features like automatic extraction, versions of which are currently used by both Gmail and Yahoo, allow you to pick out the most important pieces of information from your inbox quickly. How steep are the discounts your favorite retailer is promoting? What’s the promotion code needed to get that 15% discount on that cute sweater you’re eyeing? 

While there’s no doubt that automatic extraction is a boon to the consumer, email marketers need to be aware of its impact on email inbox previews and attribution. There’s no preventing automatic extraction from having an effect on emails, but brands can use tools like Gmail Annotations and Schema for Yahoo to exert some control over how their promotional emails look in Gmail and Yahoo inboxes.

How Automatic Extraction Works

Automatic extraction is different from Apple Intelligence in that it’s not fully summarizing your email in the preview. Instead, it uses AI technology to scan a promotional email and pull key content features like discount codes, discount percentages, sale end-dates, and images right into the inbox preview. Image previews often come with a link to the sender’s main website which, importantly, can divert people away from the desired actions of opening the email and clicking its content. At the moment, which emails are impacted by automatic extraction and which aren’t seems a bit random, but we have every reason to believe that as the technology improves, it will be applied to promotional emails more uniformly.

The Challenges of Automatic Extraction

So, what’s the problem? Well, there are a few!

First, automatic extraction today isn’t that great at pulling exactly what you the marketer would want to display in the inbox preview for your campaigns. The results can be poor or otherwise uninspiring displays of random content bits and images. Here’s an example of this particular issue from a Gmail inbox:

We suspected that automatic extraction was at play because the image pulled into the inbox wasn’t formatted well for the preview and didn’t display any actual Wolf & Badger products. When we opened the email, we were able to see that Gmail had extracted the image rather randomly from a banner towards the bottom of the email showing the brand’s flagship stores:

This seems to be a common behavior for automatic extraction: the hero image is ignored and the image that gets pulled is often whatever the first next image is.

This leads us to the second problem with automatic extraction: it can cause email attribution errors. If we go back to the Gmail inbox preview for this same Wolf & Badger email and click on the image of the store under the subject line, we are directed straight to the brand’s main webpage:

In other scenarios, automatic extraction will pull exciting bits of content– like discount codes– out of the email, thus making it unnecessary for the recipient to take the desired action of opening and clicking in the email itself. Check out this example from LL Bean:

 

Here we see the discount code is pulled right into the inbox preview. So, where did that code get pulled from? We found it buried all the way down in the small print of the email. Gmail dug deep to find that code that LL Bean seemed to want tucked away!

It’s not that LL Bean didn’t want recipients to find and use the discount code. But it does appear that their preferred method of getting you the recipient to the discount code would have been having you click on their well placed call-to-action inside of the email:

Instead, a recipient of this email could glance in their inbox, see the discount code surfaced, and head straight to llbean.com to start shopping. In the end, that would still be a revenue win, but this poses a problem for email teams: while the email is what inspired the recipient to go on a shopping spree and use that discount code, the resulting sale will not be attributed to the email. 

Sometimes as marketers, you don’t want a discount code featured prominently in the inbox preview. You may have a whole campaign hinged on an “Open to get your discount code!” type subject line to drive engagement, but automatic extraction threatens to make the act of opening the email unnecessary. New Yahoo Mail smart features envision an inbox that allows recipients to take critical actions like copying codes, adding events to a calendar, and grabbing email attachments all without opening an email or clicking an email link: 

 

Furthermore, increased email related activity happening outside of the email means that it’s even harder to establish whether or not a recipient is active. Clicks are the most reliable email activity data point for engagement based sending in a post-MPP world, and now automatic extraction threatens to decrease in-email click activity. With AI features like this making it even harder for marketers to infer interest from their subscribers, marketers are going to have to get really comfortable with simply asking their subscribers if they want to continue to receive promotional emails. This should be done frequently and programmatically for any subscribers that don’t have solid and recent signs of life (clicks, purchases, conversions, etc.). 

The Good News: Annotations and Schema

If you’re fretting and sweating while reading any of this, don’t worry, there is some good news. As opposed to Apple Intelligence summaries that you can’t assert much control over, there is a solution to push back against the sometimes random, ill-fitting previews of automatic extraction: using Gmail Annotations and Schema for Yahoo.

Gmail Annotations has been around since 2018, when Google developed it to help marketers drive value from the promotions tab. Annotations promised to “bring email messages in the Promotions tab to life with features such as images, deals, and expiration dates” (Annotate Emails in the Promotions Tab). Sound familiar? Yep, this is exactly the kind of functionality that automatic extraction is now pushing onto your promotional emails, except that if you’re using annotations, you are in control of your Gmail promotions tab previews! Annotations is built off of schema.org code base, and Gmail provides detailed instructions here for how to use various code snippets to make your emails pop out in the inbox.

Similarly, Yahoo encourages senders to embed Structured Data and Schema code in their emails to create a “rich experience for your campaigns within inboxes.” When you’re using one of these industry standard codebases in your email, Yahoo will “pull key details of your campaign like expiration dates, deal descriptions, and any images representing the deal and render them in a nicely crafted card in the most noticeable real estate of an email message.”

When you’re in control of the inbox previews of your promotional content, you can leverage previews to work with your subject line to entice your recipients to open. Check out the below example from a Gmail inbox where Neiman Marcus does just that:

 

 

You can also create professional looking, strategic image previews with annotations, like Brooks Running routinely does by taking advantage of the multi image and product carousel features:

 

Of note, too, is that if you’re using annotations, you can actually set the image URL to match the promotion you’re running, rather than having Gmail autodirect recipients to the main web page. For example, when we clicked on the “Ghost Max SE” image from the above inbox preview you’re taken to a landing page for the Ghost shoe, and if you click on the “Glycerin 22” image you’re taken to a landing page for the Glycerin shoe:

   

In short, now is the time to start leveraging Schema.org for Yahoo and Gmail Annotations. These mailbox providers are going to be creating previews one way or another– so make sure you have some say over it! And as always, test, test, test to make sure you understand what your email previews look like across a variety of mailbox providers, devices, and operating systems.

Automatic Extraction: Closing Thoughts 

If you send promotional emails, chances are, they are already being impacted by automatic extractions in Gmail and Yahoo inboxes, albeit sporadically. Instead of trying to push against this new technology, work on your email code to take the control back with Annotations and Schema. This is the only way to get consistent results. Because I can already hear someone asking the question, I’ll answer it preemptively: Yes your emails will land in Gmail promotions tab if you use Annotations. That’s where they were going to land anyway, and that’s exactly where they should land. Your recipients that are using tabs have made the decision that they want promotional emails in one folder only, so why not do a little extra coding work to make those emails pop and improve recipient experience? If you need any more convincing, just take a peek at my own promotions inbox today and think about where your attention is drawn first:

Finally, inbox previews underscore the importance of regularly checking in with your email audience members to ask if they still want to receive promotional emails. If people start interacting with content directly in the inbox, you will be able to rely less and less on open and click signals to determine who is engaged. 

Need help navigating what mailbox provider AI means for you and your brand? Our Professional Services team is a group of email industry experts here to help you optimize your email program. Reach out and let us know how we can help!

 


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