Table of Contents
In commerce, the shopping cart is both the vehicle and the signal of revenue. It’s the tell. If this were poker, it’d be the shopper tipping their hand.
Retailers spend an absurd amount of energy getting you to buy more than you planned. That’s cart expansion. But if you add items and walk away? That’s cart abandonment, and retailers treat it like a crisis.
Text Messaging and the Shopping Cart
This makes both moments ideal for SMS: short bursts of momentum right when the shopper needs it.
The best moment to send that message wasn’t after the shopper disappeared. It was while they were still leaning in. When the cart hit $42 and they hesitated. When they added a second item, then paused. When they lingered on the product page but didn’t click Add to Cart. That’s when a message could’ve made a difference. A mid-journey nudge, not an all-hands-on-deck rescue.
Not “Still thinking it over?”; not “You forgot something!”
Instead:
“Add one more, and you get free shipping.” OR
“That bundle qualifies for a faster delivery window.” OR
“Heads up—your size just dropped below five in stock.” OR
“Add $6 more, and the sampler pack’s free.”
These are timely, relevant signals tied directly to the shopper’s browsing pace. The point isn’t to shout; it’s to guide. Right place, right moment, right message.
Until recently, this kind of messaging didn’t scale.
You needed rules, copy, logic branches, and someone to wire it all together. Maybe you’d build it for your highest-value customers. Maybe for one or two flagship products. But not across the whole catalog. Not in real time. Not with context.
That’s where GenAI changes things.
How GenAI Can Change the Cart Experience
You’re no longer writing a single message and hoping it fits. You’re setting the conditions—and the system generates the right variation based on what’s in the cart, what’s in the session, and what’s about to stall. What felt like magic is now possible.
Say a shopper adds two items and pauses on the third. They’ve hovered on a product page for nineteen seconds, scrolled the reviews, and then backed out without adding the item. The old setup would wait for that to become an abandoned cart and then send a one-size-fits-all “Still thinking it over?” message an hour later.
With GenAI, the system sees that pause and generates something smarter, right there in session:
“Looks like you’re building a bundle. Add one more, and it qualifies for free shipping.” OR
“That item pairs well with what’s already in your cart. Want to take a look?”
It is generating the message in real time, based on context, tone, and cart behavior. You’re keeping pace with the shopper’s intent, not chasing the cart.
But Not Without The Shopper’s Permission
None of this works without opt-in. Texting someone while they’re still shopping only works if they’ve already said yes. Otherwise, it doesn’t matter how good the message is or how perfect the timing feels—it still lands wrong. Helpfulness becomes invasive fast.
This is where most brands get it twisted. They treat SMS like just another behavioral trigger. But texting feels closer. More personal. You don’t get to just show up there uninvited.
Here’s one way to earn the shopper’s permission: The shopper lands on your site and starts building their cart, and a soft prompt appears:
“Want help as you shop? Our SMS assistant can nudge you with free shipping, restock alerts, or bundle deals—just while you’re browsing.”
[Yes, text me tips] [No, thanks]
That’s service with consent. Clear value. Clear choice. Clear opt-in. Once they’ve said yes, the message feels like a personal shopper, a confidante, not a store clerk chasing you down the aisle.
Yes, These Systems Still Hallucinate
It would be irresponsible to pretend that this is all upside. Because these LLMs know so much and can share what they know so confidently, it can lull us into thinking that they’re always right. Sure, GenAI is fast, flexible, and context aware. But for reasons no one really knows, it still makes things up.
Poorly implemented, it will invent SKUs, misprice bundles, and offer return policies you’ve never approved. It’ll sound calm and confident the whole time.
So, no, you don’t let these systems run wild in your checkout flow. You don’t feed them your product catalog and hope for the best. You constrain them. You limit what they can say. You train them on actual business logic—pricing rules, fulfillment windows, promo thresholds—and monitor what they generate. Not once, but constantly.
The goal isn’t creativity. It’s personalization and correctness at scale. You’re not hiring a writer. You’re tuning a system. One that has to be right.
Done well, GenAI doesn’t replace your rules. It just scales them—faster, broader, and with better timing than any copywriter/developer combo could do together.
Sidebar: Brick and Mortar Figured This Out Long Ago
Cart expansion and cart abandonment aren’t new problems. Brick-and-mortar retailers have been designing around them for decades.
It’s no accident that the good stores greet you with a smile and hand you a basket. A light act of generosity, paired with a friendly face, creates a small social contract—what Robert Cialdini called reciprocity. You accepted the basket, so you’re just a little more likely to use it.
It’s also no accident that Costco doesn’t tell you what’s down which aisle. It’s structured wandering. You find the thing you didn’t know you wanted because they made you pass five other things first.
Retailers have always known that intent needs space—and a little friction—to grow.
Sam Walton understood this better than most. He used to walk his stores. Watch what people picked up. What they put back. Where they paused. And more importantly, where they turned around. He didn’t call it cart abandonment. He just knew when someone had lost the thread. He called it listening to the customer.
Finally
The shopping cart is one of the purest signals in commerce. Expansion means curiosity. Abandonment means hesitation. And both moments are rich with intent—if you’re paying attention.
The job of SMS isn’t to chase the cart after it’s gone cold. It’s to meet the shopper in motion. A message that’s timely, relevant, and respectful does more than convert; it creates affinity and loyalty.
GenAI finally gives us the tools to scale that kind of message. But only if we use it with care.
Train it well. Set guardrails. Ask permission. And remember: The goal isn’t automation. It’s attentiveness. Because the shopper is already signaling. You just need to know when to lean in and what to say.