From early TV advertising all the way to e-commerce, holiday shopping has always evolved alongside technology. Then smartphones changed where and when customers shopped. Omnichannel retail blurred the line between digital and physical experiences, and now, AI is beginning to sit across all of them.
There’s no denying that AI seriously influenced the 2024 and 2025 holiday seasons. But 2026 may be the first truly AI-native holiday shopping season, where artificial intelligence is no longer just an experimental nice-to-have sitting beside the customer journey.
The shift is already visible. Adobe Analytics found that traffic from generative AI tools to U.S. retail websites increased 693.4% year over year during the 2025 holiday season. Salesforce estimates that AI and agents influenced $262 billion in global holiday spending last year. Meanwhile, Deloitte expects 2026 holiday retail sales to reach between $1.70 trillion and $1.71 trillion, with e-commerce growing as much as 8.4%.
This enormous opportunity for retailers also creates a customer experience challenge that brands should be addressing now. The more tech-enabled CX becomes, the more opportunities it has to break your current workflows and underdeliver on your desired brand experiences.
A much larger chunk of customers now begin their journey with an AI conversation instead of a search bar. Target reported that AI-driven traffic to its website increased 2,000% year over year in the first quarter of 2026, and the retailer has expanded shopping experiences across Google and Gemini, Microsoft Copilot, and ChatGPT.
There’s an important catch to this, though. Recent Contentsquare research found that 21% of consumers have received information from an AI shopping assistant that differed from what they later found on a brand’s website. And when an AI-recommended purchase leads to a disappointing website experience, only 3% of consumers say they would complete the purchase anyway. Nearly one-quarter would switch brands. For years, retailers worked toward creating a single source of truth for their customers. AI just introduced another one.
And the potential disconnect extends well beyond the website. Imagine a customer who uses AI to select a gift, visits the retailer’s website, receives another AI-powered recommendation, places a BOPIS order, visits the store, asks an associate a product question, and later starts a return through an automated chatbot before being transferred to a human agent. That is one purchase containing AI, digital, physical, AND human interactions.
A conversion dashboard can tell you the sale happened, a customer survey can tell you whether the shopper was satisfied, but neither necessarily tells you where the experience almost broke.
That’s why the better question for retail leaders isn’t simply, “Where can we use AI?”
It is: Where should AI lead, where should humans lead, and how should we measure each experience?
The AI-Human CX Matrix For Holiday Retailers
Earlier this year, our Founder & CEO Ron introduced an AI-Human CX Measurement Matrix built around two questions: Is the customer’s situation predictable or ambiguous? And is the customer emotionally neutral or emotionally charged?
For holiday retail, those four quadrants become especially important.
Predictable + Emotionally Neutral
Think: “What’s the status of my delivery?”
These are ideal AI-led interactions. Customers usually want a fast, correct answer—not a relationship-building conversation. Brands should measure accuracy, resolution time, and whether the customer needs additional support afterward.
As Ron put it: “Fast-but-wrong still fails.”
Predictable + Emotionally Charged
Now change the question: “My child’s gift was supposed to arrive yesterday. Where is it?”
The underlying information may still be simple, but the customer’s emotional state has changed.
AI can retrieve shipping information or accelerate resolution, but human accountability may become much more valuable. Measurement should consider empathy, tone, escalation, and whether the interaction actually reduced the customer’s stress.
Ambiguous + Emotionally Neutral
Now the question may be: “I want to buy a laptop for my daughter for Hanukkah. Which one should I get?”
There may not be one objectively correct answer. AI can narrow choices and provide recommendations, while a knowledgeable associate can add context and judgment.
Here, brands should be evaluating recommendation quality, consistency, product knowledge, and whether employees confidently understand (or contradict) the guidance customers are receiving digitally.
Ambiguous + Emotionally Charged
Finally: “The main gift I ordered arrived damaged two days before Christmas. What are you going to do about it?”
These are trust-critical moments.
The customer isn’t simply looking for information. They want someone to understand the situation, make a judgment call, and take responsibility.
Pressure-Test Your Holiday Customer Experience Before Black Friday
Holiday volume amplifies CX problems. An inventory mismatch affecting a small percentage of customers in September becomes much more serious at peak volume. Likewise, a confusing AI-to-agent handoff becomes harder to manage when service demand spikes.
Retailers: Black Friday is your main event for the year, not the time to be testing your CX.
This means looking beyond whether individual systems are technically working. Is the chatbot giving customers accurate information? Does that information match what they hear from an associate? Does online inventory reflect what is actually available in-store? Can employees explain the products and promotions customers discovered through AI? When an automated interaction needs human judgment, is the transition seamless?
Retail leaders should be pressure-testing these experiences now: chatbot accuracy, online-to-store inventory, BOPIS, promotions, employee product knowledge, returns, AI-to-human escalations, and the emotionally charged scenarios where good judgment matters most. And no single measurement tool captures that entire journey.
Know Your CX Before Your Customers Test It for You
The 2026 holiday season will not be the first touched by AI.
It may be the first where AI is embedded deeply enough across discovery, shopping, service, and store operations that retailers can no longer treat it as a separate channel.
The winning will understand where AI improves the experience, where human judgment remains essential, and where the handoffs between the two create friction customers can feel.
September and October are the opportunity to find those gaps, correct them, and build a stronger holiday customer experience before traffic peaks. Because this holiday season, customers are going to test your technology, your people, and every handoff in between.
