Yahoo Mail is rolling out a new artificial intelligence feature called “Catch Up,” a move that signals the company’s deeper foray into AI as it seeks to modernize and regain relevance in an era dominated by competitors like Gmail and Outlook.
The feature, exclusive to Yahoo Mail’s iOS and Android mobile apps, aims to help users instantly skim through their unread emails with AI-powered summaries and intuitive inbox sorting—presented in a “game-like experience” to make email feel less like work.
To promote the launch, Yahoo has partnered with streetwear label Anti Social Social Club on a limited-edition apparel line dubbed “The Anti Email Email Club.” The collaboration includes T-shirts and sweatshirts and is accompanied by a campaign video featuring comedian Morgan Jay, portraying the chaos of managing incoming emails and how the new AI feature eases the burden.
According to Yahoo, the tool was developed in response to how younger users—Millennials and Gen Z—engage with email. A Pollfish survey commissioned by Yahoo Mail found that while 70% of respondents check their personal email multiple times a day, about half reported missing key events due to a cluttered or overwhelming inbox. Yahoo Mail claims that its AI-powered tool is the first of its kind among email platforms and is designed to streamline this growing demand for more intelligent and intuitive communication management.
Kyle Miller, general manager of Yahoo Mail, said the company is rethinking the email experience to make it less of a burden.
“We’re all ‘anti email’ when it becomes another tiring task,” he said. “If you’re anti how email has worked for decades — welcome to our club.”
A Push for Revival
Yahoo’s latest AI push is more than a product upgrade—it’s part of a broader effort to revive the company’s identity and re-establish a competitive foothold in the internet landscape it once ruled. Founded in 1994 as one of the first web directories and portals, Yahoo was an early leader in email, news aggregation, search, and online advertising. By the early 2000s, Yahoo Mail was the most widely used webmail service globally, dominating the inboxes of millions.
But a series of strategic missteps and missed opportunities eventually sent Yahoo into a long decline. In 2002, Yahoo had the chance to buy Google for $5 billion but walked away. In 2006, it failed to acquire Facebook for $1 billion after backing out of a deal. In 2008, Yahoo rejected a $44.6 billion takeover offer from Microsoft, a decision widely criticized after the company’s market value continued to plummet.
The rise of Gmail, with better storage, smarter spam filters, and faster updates, began to erode Yahoo Mail’s dominance. In 2013, Yahoo suffered a massive data breach that eventually affected all 3 billion of its user accounts—a PR and trust disaster that further weakened the brand.
Despite once being valued at over $125 billion, Yahoo was sold in 2017 to Verizon for just $4.48 billion, and its internet business was merged under a new division called Oath, which also included AOL. In 2021, Verizon sold Yahoo to private equity firm Apollo Global Management for $5 billion, marking a new chapter in the company’s long road to reinvention.
Now operating under Yahoo Inc., the company is trying to rebuild its brand through AI, tapping into the current wave of interest surrounding generative technologies. While competitors like Google have begun integrating AI across their services—such as Gmail’s Smart Reply and Smart Compose—Yahoo’s move with “Catch Up” is a notable attempt to leapfrog years of stagnation and speak directly to mobile-first, younger users who grew up with faster, sleeker alternatives.
While the stakes are high, Yahoo is betting that by blending utility with playful branding—like the “Anti Email Email Club” streetwear—it can begin carving out a niche that’s both functional and culturally resonant. The apparel line, priced between $55 and $99, is available for preorder on Anti Social Social Club’s website.
Only time will tell whether “Catch Up” becomes a turning point. But for a company that helped define the early internet, Yahoo’s return to innovation may be its best shot at rewriting its legacy in the AI age.