Tech
Can AI Avoid the Enshittification Trap?
I recently vacationed in Italy. As one does these days, I ran my itinerary past GPT-5 for sightseeing suggestions and restaurant recommendations. The bot reported that the top choice for dinner near our hotel in Rome was a short walk down Via Margutta. It turned out to be one of the best meals I can remember. When I got home, I asked the model how it chose that restaurant, which I hesitate to reveal here in case I want a table sometime in the future (Hell, who knows if I’ll even return: It is called Babette. Call ahead for reservations.) The answer was complex and impressive. Among the factors were rave reviews from locals, notices in food blogs and the Italian press, and the restaurant’s celebrated combination of Roman and contemporary cooking. Oh, and the short walk.
Something was required from my end as well: trust. I had to buy into the idea that GPT-5 was an honest broker, picking my restaurant without bias; that the restaurant wasn’t shown to me as sponsored content and wasn’t getting a cut of my check. I could have done deep research on my own to double-check the recommendation (I did look up the website), but the point of using AI is to bypass that friction.
The experience bolstered my confidence in AI results but also made me wonder: As companies like OpenAI get more powerful, and as they try to pay back their investors, will AI be prone to the erosion of value that seems endemic to the tech apps we use today?
Word Play
Writer and tech critic Cory Doctorow calls that erosion “enshittification.” His premise is that platforms like Google, Amazon, Facebook, and TikTok start out aiming to please users, but once the companies vanquish competitors, they intentionally become less useful to reap bigger profits. After WIRED republished Doctorow’s pioneering 2022 essay about the phenomenon, the term entered the vernacular, mainly because people recognized that it was totally on the mark. Enshittification was chosen as the American Dialect Society’s 2023 Word of the Year. The concept has been cited so often that it transcends its profanity, appearing in venues that normally would hold their noses at such a word. Doctorow just published an eponymous book on the subject; the cover image is the emoji for … guess what.
If chatbots and AI agents become enshittified, it could be worse than Google Search becoming less useful, Amazon results getting plagued with ads, and even Facebook showing less social content in favor of anger-generating clickbait.
AI is on a trajectory to be a constant companion, giving one-shot answers to many of our requests. People already rely on it to help interpret current events and get advice on all sorts of buying choices—and even life choices. Because of the massive costs of creating a full-blown AI model, it’s fair to assume that only a few companies will dominate the field. All of them plan to spend hundreds of billions of dollars over the next few years to improve their models and get them into the hands of as many people as possible. Right now, I’d say AI is in what Doctorow calls the “good to the users” stage. But the pressure to make back the massive capital investments will be tremendous—especially for companies whose user base is locked in. Those conditions, as Doctorow writes, allow companies to abuse their users and business customers “to claw back all the value for themselves.”
When one imagines the enshittification of AI, the first thing that comes to mind is advertising. The nightmare is that AI models will make recommendations based on which companies have paid for placement. That’s not happening now, but AI firms are actively exploring the ad space. In a recent interview, OpenAI CEO Sam Altman said, “I believe there probably is some cool ad product we can do that is a net win to the user and a sort of positive to our relationship with the user.” Meanwhile, OpenAI just announced a deal with Walmart so the retailer’s customers can shop inside the ChatGPT app. Can’t imagine a conflict there! The AI search platform Perplexity has a program where sponsored results appear in clearly labeled follow-ups. But, it promises, “these ads will not change our commitment to maintaining a trusted service that provides you with direct, unbiased answers to your questions.”
Tech
The Best Presidents’ Day Deals on Gear We’ve Actually Tested
Presidents’ Day Deals have officially landed, and there’s a lot of stuff to sift through. We cross-referenced our myriad buying guides and reviews to find the products we’d recommend that are actually on sale for a truly good price. We know because we checked! Find highlights below, and keep in mind that most of these deals end on February 17.
Be sure to check out our roundup of the Best Presidents’ Day Mattress Sales for discounts on beds, bedding, bed frames, and other sleep accessories. We have even more deals here for your browsing pleasure.
WIRED Featured Deals
Branch Ergonomic Chair Pro for $449 ($50 off)
The Branch Ergonomic Chair Pro is our very favorite office chair, and this price matches the lowest we tend to see outside of major shopping events like Black Friday and Cyber Monday. It’s accessibly priced compared to other chairs, and it checks all the boxes for quality, comfort, and ergonomics. Nearly every element is adjustable, so you can dial in the perfect fit, and the seven-year warranty is solid. There are 14 finishes to choose from.
Tech
Zillow Has Gone Wild—for AI
This will not be a banner year for the real estate app Zillow. “We describe the home market as bouncing along the bottom,” CEO Jeremy Wacksman said in our conversation this week. Last year was dismal for the real estate market, and he expects things to improve only marginally in 2026. (If January’s historic drop in home sales is indicative, that even is overoptimistic.) “The way to think about it is that there were 4.1 million existing homes sold last year—a normal market is 5.5 to 6 million,” Wacksman says. He hastens to add that Zillow itself is doing better than the real estate industry overall. Still, its valuation is a quarter of its high-water mark in 2021. A few hours after we spoke, Wacksman announced that Zillow’s earnings had increased last quarter. Nonetheless, Zillow’s stock price fell nearly 5 percent the next day.
Wacksman does see a bright spot—AI. Like every other company in the world, generative AI presents both an opportunity and a risk to Zillow’s business. Wacksman much prefers to dwell on the upside. “We think AI is actually an ingredient rather than a threat,” he said on the earnings call. “In the last couple years, the LLM revolution has really opened all of our eyes to what’s possible,” he tells me. Zillow is integrating AI into every aspect of its business, from the way it showcases houses to having agents automate its workflow. Wacksman marvels that with Gen AI, you can search for “homes near my kid’s new school, with a fenced-in yard, under $3,000 a month.” On the other hand, his customers might wind up making those same queries on chatbots operated by OpenAI and Google, and Wacksman must figure out how to make their next step a jump to Zillow.
In its 20-year history—Zillow celebrated the anniversary this week—the company has always used AI. Wacksman, who joined in 2009 and became CEO in 2024, notes that machine learning is the engine behind those “Zestimates” that gauge a home’s worth at any given moment. Zestimates became a viral sensation that helped make the app irresistible, and sites like Zillow Gone Wild—which is also a TV show on the HGTV network—have built a business around highlighting the most intriguing or bizarre listings.
More recently, Zillow has spent billions aggressively pursuing new technology. One ongoing effort is upleveling the presentation of homes for sale. A feature called SkyTour uses an AI technology called Gaussian Splatting to turn drone footage into a 3D rendering of the property. (I love typing the words “Gassian Splatting” and can’t believe an indie band hasn’t adopted it yet.) AI also powers a feature inside Zillow’s Showcase component called Virtual Staging, which supplies homes with furniture that doesn’t really exist. There is risky ground here: Once you abandon the authenticity of an actual photo, the question arises whether you’re actually seeing a trustworthy representation of the property. “It’s important that both buyer and seller understand the line between Virtual Staging and the reality of a photo,” says Wacksman. “A virtually staged image has to be clearly watermarked and disclosed.” He says he’s confident that licensed professionals will abide by rules, but as AI becomes dominant, “we have to evolve those rules,” he says.
Right now, Zillow estimates that only a single-digit percentage of its users take advantage of these exotic display features. Particularly disappointing is a foray called Zillow Immerse, which runs on the Apple Vision Pro. Upon rollout in February 2024, Zillow called it “the future of home tours.” Note that it doesn’t claim to be the near-future. “That platform hasn’t yet come to broad consumer prominence,” says Wacksman of Apple’s underperforming innovation. “I do think that VR and AR are going to come.”
Zillow is on more solid ground using AI to make its own workforce more productive. “It’s helping us do our job better,” says Wacksman, who adds that programmers are churning out more code, customer support tasks have been automated, and design teams have shortened timelines for implementing new products. As a result, he says, Zillow has been able to keep its headcount “relatively flat.” (Zillow did cut some jobs recently, but Wacksman says that involved “a handful of folks that were not meeting a performance bar.”)
Tech
Do Waterproof Sneakers Keep the Slosh In or Out? Let WIRED Explain
Running with wet feet, in wet socks, in wet shoes is the perfect recipe for blisters. It’s also a fast track to low morale. Nothing dampens spirits quicker than soaked socks. On ultra runs, I always carry spares. And when faced with wet, or even snowy, mid-winter miles, the lure of weatherproof shoes is strong. Anything that can stem the soggy tide is worth a go, right?
This isn’t as simple an answer as it sounds. In the past, a lot of runners—that includes me—felt waterproof shoes came with too many trade-offs, like thicker, heavier uppers that change the feel of your shoes or a tendency to run hot and sweaty. In general, weatherproof shoes are less comfortable.
But waterproofing technology has evolved, and it might be time for a rethink. Winterized shoes can now be as light as the regular models, breathability is better, and the comfort levels have improved. Brands are also starting to add extra puddle protection to some of the most popular shoes. So it’s time to ask the questions again: Just how much difference does a bit of Gore-Tex really make? Are there still trade-offs for that extra protection? And is it really worth paying the premium?
I spoke to the waterproofing pros, an elite ultra runner who has braved brutal conditions, and some expert running shoe testers. Here’s everything you need to know about waterproof running shoes in 2026. Need more information? Check out our guide to the Best Running Shoes, our guide to weatherproof fabrics, and our guide to the Best Rain Jackets.
Jump To
How Do Waterproof Running Shoes Work?
On a basic level, waterproof shoes add extra barriers between your nice dry socks and the wet world outside. If you’re running through puddles deep enough to breach your heel collars, you’re still going to get wet feet. But waterproof shoes can protect against rain, wet grass, snow, and smaller puddles.
Gore-Tex is probably the most common waterproofing tech in footwear, but it’s not the only solution in town. Some brands have proprietary tech, or you might come across alternative systems like eVent and Sympatex. That GTX stamp is definitely the one you’re most likely to encounter, so here’s how GTX works.
The water resistance comes from a layered system that is composed of a durable water repellent (DWR) coating to the uppers with an internal membrane, along with other details like taped seams, more sealed uppers with tighter woven mesh, gusseted tongues, and higher, gaiter-style heel collars.
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