Gamified inboxes and purple nostalgia: Yahoo Mail bets on AI to win back Gen Z

Yahoo Mail is betting on artificial intelligence and mobile-first design to reinvent itself for a younger, digitally native audience. In a bid to streamline the inbox experience, the company has announced the rollout of a new ‘Catch Up’ feature on Thursday.

Once a dominant player that survived the dot-com bubble, Yahoo gradually lost relevance following major data breaches and its eventual acquisition by Verizon. An existence that did not seem to impact all those existing on the internet. The brand faded into the background of the internet landscape. To recapture its relevance, Yahoo is now investing heavily in AI tools and advertising strategies.

The question remains whether this revamp of Yahoo Mail is a meaningful step forward. The new features signal a clear intent to modernise and appeal to a new generation of users, but success will depend on how well these changes resonate in a crowded and competitive digital space.

What is the Catch Up feature?

This is an AI-powered tool exclusive to its mobile app (iOS and Android), designed to help users clean up unread emails quickly through a swipe-and-tap interface.

“We are evolving Yahoo Mail to be the best personal email service, built to take the stress out of a busy inbox and make email look and feel less like work. We’re all anti email when it becomes another tiring task,” said Kyle Miller, GM, Yahoo Mail.

According to Yahoo’s internal research, nearly 70% of Gen Z and Millennials check their personal inboxes multiple times a day, yet almost half admit to missing important events due to clutter or overload. The ‘Catch Up’ feature aims to tackle the pain point by summarising unread emails with AI-generated previews and letting users decide, within seconds, whether to delete or retain each message. Completing the task triggers a gamified reward screen, reflecting the number of emails cleared and time taken.

This effort marks the first in a series of feature enhancements Yahoo is planning as part of a larger push to reposition itself as a modern personal email platform, particularly for younger users. Yahoo claims that over 50% of its mail service’s user base today is Gen Z or Millennial, a demographic more likely to prefer fast, intuitive, mobile-first tools.

“With Yahoo Mail, personal email is quick and easy to sort and manage, with game-like experiences that are built for mobile, and relevant AI-powered tools integrated throughout,” Miller added.

Earlier this year, Yahoo Mail had achieved its highest single-day user count in the last three decades, Rob Gelick, GM, Yahoo Mail, had shared in a LinkedIn post.

Not leaving a stone unturned for repositioning the brand

To promote the rollout of its new AI features, Yahoo partnered with streetwear brand Anti Social Social Club for a limited-edition line titled “Anti Email Email Club.” The collaboration, paired with influencer marketing led by creator Morgan Jay, is part of a broader effort to build cultural relevance and attract Gen Z users.

As part of its brand overhaul, Yahoo appointed Josh Line as its new chief marketing officer. Previously Paramount Global’s chief brand officer, Line is tasked with overseeing global marketing, user acquisition, and customer engagement. In an interview with the Wall Street Journal, Line said Yahoo has "almost latent brand love" among users as "one of the OGs of the internet," and that the challenge is to reignite that emotional connection while driving growth.

Visually, Yahoo is embracing a fun, purple, cartoonish design across its platforms. Oversize cursors and early web-style graphics play into a deliberate nostalgia strategy. Its info page now describes Yahoo as "a nice place to stay on the internet," reflecting a softer, more welcoming tone compared to algorithm-heavy rivals. This retro-friendly approach coincides with growing fatigue toward major tech platforms, positioning Yahoo as a quirky, alternative internet space.

Across all verticals, beyond design and branding, making regular acquisitions and forging strategic partnerships has long been part of Yahoo’s playbook. Yahoo Finance recently teamed up with Forge Global to offer Private Company Insights, allowing users to access and review data on pre-IPO startups. The platform now enables browsing private company share prices alongside publicly listed ones, a feature traditionally reserved for institutional investors.

Altogether, Yahoo is attempting a comeback that blends nostalgic appeal with forward-looking tools. Whether these efforts can revive its long-dormant influence remains to be seen, but the company is clearly not content with simply existing in the background of the internet.

How does Yahoo mail stack up against its competitors?

Yet, Yahoo still seems to only ‘Catch Up’ with its biggest competitor Google, who started rolling out features of Gemini integration into Gmail since June last year. Gemini offers users smart replies and summarised email content based on AI-generated context.

But what sets Yahoo apart from Gemini is that former takes a different route by gamifying the experience. The Catch Up screen creates a sense of accomplishment for users, encouraging repeated engagement. This playful design may resonate with younger users, particularly Gen Z, but may not appeal to the larger professional audience that dominates rival platforms.

While this could improve retention, it may not be enough to expand Yahoo’s share in an email market still dominated by Gmail and Apple Mail. Gmail remains the global leader in email usage, and Apple Mail continues to benefit from seamless integration with iOS devices. Regaining relevance, and not just innovating, remains Yahoo’s bigger challenge in an industry it once led.

According to Litmus Email Analytics' May 2025 report based on over 1.3 billion email opens, Apple accounted for 51.52% of all email opens, Gmail for 26.72%, Outlook for 7%, and Yahoo Mail a modest 2.15%.

However, Yahoo Mail shows signs of life in other metrics. According to Similarweb data, Yahoo Mail has exceeded Gmail in monthly website visits between March and May this year, suggesting higher discoverability. This may also be because Gmail has reached a near-saturation point in terms of user growth.

Following its summer revamp, Yahoo reported a 125% increase in users connecting their Gmail accounts to Yahoo Mail on desktop. On iOS, Yahoo Mail’s monthly active users have been growing at double-digit rates year over year, according to a Business Insider report.

Still, Yahoo’s greater challenge lies not in retention or engagement, but in expanding its user base. For meaningful growth, it must either convert users from rival platforms or attract new internet users altogether. But conversion is difficult in the email space, where habits, loyalty, and convenience strongly influence user behaviour.

The second hurdle is the overall stagnation in the growth of global email users. According to Statista, the number of global email users is expected to see a slowdown compared to earlier periods. From 2018 to 2020, the email user base grew 8%, but between 2023 and 2025, it is projected to grow just over 5%. In other words, while email remains relevant, the pie is no longer expanding quickly, that will make it harder for Yahoo to grow its share.

Yahoo’s efforts to modernise and attract younger users are timely, but in a mature market with slowing growth, the real challenge will be winning over users already committed to other platforms.

But privacy concerns also prevail

While the integration of AI into email services may seem like a compelling leap forward, it inevitably raises serious questions about privacy. Emails often contain highly sensitive information, making the stakes far higher than in casual, consumer-facing applications.

When Google began rolling out Gemini features for Gmail, many users expressed discomfort at the idea of a generative AI scanning their inbox. Google recently took it a step further when it introduced personalised smart replies designed to match a user’s typical tone and context, using past emails and Drive files as a base. The problem is that these features raise red flags about data misuse.

For Yahoo, this issue is especially delicate. The company suffered a major blow in 2013 when all 3 billion of its accounts were compromised in what remains one of the largest data breaches in history. Its decline accelerated after this, worsened by its failure to adapt to the mobile era. Verizon acquired Yahoo in 2016 for less than $5 billion, and it was later sold to Apollo Global Management in 2021. By then, Yahoo had already faded from relevance, overshadowed by Google and Meta.

Given that legacy, Yahoo’s recent AI push must be handled with caution. The Catch Up feature and other tools aimed at Gen Z users are part of a broader strategy to position the platform as a productivity companion. But the introduction of AI into email, without clear communication and airtight privacy protections, might pose the risk of repeating the very history Yahoo has been trying to move past.