If you were watching the tickers on Monday, you saw it. Shopify stock didn't just move; it leaped. A 6% jump in a single session isn't typical for a mature giant, but Monday, September 29, 2025, wasn't a typical day at the Ottawa headquarters.
The big reveal? A massive, "no-turning-back" partnership with OpenAI.
Honestly, it's the kind of news that makes you realize the old way of "searching" for products—typing keywords into a bar and scrolling through sponsored results—is basically becoming a relic. Shopify and Etsy both jumped on the train, but Shopify’s integration is the one that’s going to shake up your dashboard if you're a merchant.
What Actually Happened with Shopify News Sep 29 2025?
Basically, ChatGPT is becoming a storefront.
The deal allows OpenAI’s chatbot to tap directly into Shopify’s massive product catalog—we’re talking hundreds of millions of items. In the past, if you asked an AI for a gift idea, it might give you a list and some dead links. Now, it pulls real-time inventory. You can find it, see it, and buy it without ever leaving the chat interface.
Vanessa Lee, Shopify’s VP of Product, called this a shift toward "conversational commerce." She's right. People aren't just clicking ads anymore; they’re asking their AI assistants to solve problems. "Find me a waterproof jacket for a trip to Iceland that fits a tall frame." Before, you'd spend twenty minutes on Google. Now, the AI just shows you the Shopify merchant’s jacket and handles the flow.
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The Stock Market Reacted Fast
Wall Street (and Bay Street) loved the news. Shopify's price hit $207.46 on the Toronto Stock Exchange. Why the hype? Because Shopify is finding a way to bypass the "Google Tax." For years, merchants have been squeezed by rising Meta and Google ad costs. If Shopify can funnel buyers through AI conversations where the intent is already high, they’ve just built a massive new customer acquisition channel that doesn't rely on the old search giants.
The Sidekick Evolution and "Voice Mode"
While the OpenAI headlines grabbed the front page, some smaller, equally cool updates dropped for the platform's internal tools.
Sidekick—that AI assistant sitting in your admin panel—now has a full-blown Voice Mode. You can literally talk to your store. If you're in the warehouse with your hands full, you can ask Sidekick to "read me the last three high-value orders" or "generate a 20% discount code for the winter collection."
It’s also got a new fullscreen mode. Sometimes you need more than a sidebar to plan a strategy, and the new interface lets you have long-form "brainstorming" sessions with the AI about your business data.
Not All Sunshine: The Antitrust Shadow
You can't talk about Shopify news Sep 29 2025 without mentioning the legal heat. While the AI deals were being signed, a significant antitrust suit from Sezzle was making waves in the background.
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The core of the issue? "Buy Now, Pay Later" (BNPL).
Sezzle is alleging that Shopify is playing favorites with its own Shop Pay Installments. The claim is that Shopify makes it harder for merchants to use third-party BNPL providers by charging extra fees or redirecting customers. It’s a classic "platform vs. partner" fight. If you’re a merchant who relies on specific financing tools, this is the story to watch over the next few months. It could change how your checkout looks.
New Tools You Should Actually Use
The dev team didn't just focus on the "big" AI stuff. They quietly rolled out some features that actually solve daily headaches.
- Instant Add to Cart from Search: This is huge for conversion. Customers can now hit "buy" directly from the search suggestions. No more clicking through to a product page just to add a basic item to the cart.
- Filter by Metafields: You can finally filter your order list by up to five custom metafields. If you have special handling requirements or internal SKU notes, you don't have to hunt for them anymore.
- Category Metafield Support: This gives you way more control over how your products are filtered and displayed, keeping your "merchandising" tight without needing a custom app.
The Reality Check: Support Struggles
It’s worth noting—and users are definitely talking about this in the forums—that as Shopify gets "smarter" with AI, the human touch is getting harder to find.
There’s been a lot of noise lately about the decline in support quality. Merchants are reporting being stuck in chat loops for hours or having tickets passed between four different "advisors" without a fix. It’s the growing pain of 2025. Shopify is leaning so hard into "Agentic Commerce" (AI doing the work) that the human safety net feels a bit thin right now.
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What You Should Do Next
If you're running a store, the OpenAI integration isn't something to ignore. You need to make sure your product data is "AI-ready."
Check your product descriptions. The AI pulls from your data to recommend products. If your descriptions are just a list of specs, the AI won't know "why" to recommend you for a specific human problem. Use natural language.
Turn on "Instant Add to Cart." Go to your Search & Navigation settings and enable it. It’s a low-effort way to potentially bump your conversion rate by 2–5% just by removing one extra click.
Audit your BNPL options. With the Sezzle lawsuit ongoing, keep an eye on your processing fees. If you're paying a premium to use a third-party provider, it might be time to see if Shop Pay Installments actually makes more financial sense for your specific margin, even if the "default" push feels a bit forced.
Shopify is clearly trying to become the "Operating System" of the AI era. Whether you like the "agentic" future or not, the tools are shifting, and Monday's news was the starting gun for a very different kind of holiday season.