Hotmail’s Journey from Internet Must-Have to Laughing Stock

Microsoft’s email service was once the cutting edge in online communication. Now, it’s a relic from the days of dial-up internet. What happened?
Photos via Alamy and Wikimedia Commons.

I’m staring at a photo of three women’s bums. Shot from behind, their bodies are cut off from the waist and each wears a pair of garishly branded Evisu jeans. A “BUY NOW” button flashes intermittently over the photo. I have never Googled “Evisu” and have no desire to purchase a pair of women’s jeans. And yet, this advert continues to stare at me from the sidebar of my Hotmail inbox.

When Microsoft launched Hotmail in 1996, no one cared about the ads. Finally, emails had a web-based home and were completely free to send and receive. Before that, email was only accessible through desktop or other non web-based services, which often cost money and relied on clunky interfaces. Three years after Hotmail's launch, its email address also gave you access to MSN Instant Messenger, Microsoft’s new instant chat service that millennials spent all night using to message the same friends they’d just seen at school, causing intense arguments over custody of the family desktop computer.


It was only in 2004, when Gmail came along with its ad-free, sleek design and supposedly user-friendlier server, that people started to question whether Hotmail was really the best email could do. Many made the switch from what they knew – Evisu ads included – to the updated world: one that was fully integrated with the new ever-evolving internet superpower Google.

To achieve online dominance, Gmail had to be better than Hotmail in every way. It began by tantalising users with a one gigabyte storage capacity – 500 times more than Hotmail’s offering. The new server also introduced a scanning tool, which identified keywords that could be used for advertising purposes. But perhaps most impressive was Gmail’s instant search tool, now a standard feature in all inboxes. (How else would you find that Yodel confirmation email from over five weeks ago?) In 2012, Gmail surpassed Hotmail’s 360 million monthly active users, achieving 425 million, and is now thought to have close to 1.5 billion users – compared to Hotmail’s 400 million.

“The initial appeal of Gmail was its integration with the G-suite tools – like Drive, Sheets – and its collaborative aspects like Hangouts, and live editing,” Alex Oakley, an IT consultant based in London, tells me. “Ultimately, everyone preferred the look, feel and experience of it because everyone thought Google was sexy and that Hotmail wasn’t.”

While many abandoned their Hotmail accounts for Gmail, there are still a committed few who won't let go of their addresses. Lady Kitt, a 29-year-old Hotmail remainer living in Newcastle, agrees. “It’s nostalgic, comforting, familiar and a bit clunky – like going to that shitty pub where you had your first underage drink. I can track most of my adulthood through my account,” they say. “It’s like personal archaeology in there.” Indeed, one of Hotmail’s greatest strengths is that it harks back to an easier, more innocent time on the internet. A time when I was entitled – nay, encouraged – to use the email address for over five years, and no one batted an eyelid.


However, there are practical reasons for sticking with Hotmail in the face of Gmail’s dominance, too. “I’m horrifically dyslexic,” Kitt says. “I find it hard to remember any new email address I try to make, let alone navigate the totally unworkable inbox once I get in there.” So for some, the accessibility of something like Hotmail, which has seemingly always been there, is a matter of necessity.

For others, it’s about optics. While Hotmail seems adolescent, Gmail is viewed as the more grown-up choice. Safiyyah Choycha, 32, from Birmingham, says she made the switch to Gmail when she became a full-time artist, because she was advised by her website designer that it looked more professional to use a “newer account”. Even though she still finds Hotmail “so much easier” to use – “probably because it’s where I learnt how to email when I was 17” – Choycha says she will only use it personally, never professionally.

The professionalism of a Hotmail email address is an ongoing topic of debate. Sree Sreenivasan found himself in a very public LinkedIn row in 2018, when he posted to his profile: “When you see a resume with a Hotmail address, what do you do? Treat ’em same as others? Reject ’em right away?” One response read: “If my email doesn’t get me the job, then I didn’t want it to begin with!” Another countered this with: “If you’re still using Hotmail, you don’t understand modern technology. Simple!” Email snobbery doesn’t stop there. Both the Telegraph and Poynter have published articles advising readers not to apply for jobs using a Hotmail – or “vintage” as Poynter calls it – domain.


When Hotmail relaunched as Outlook in 2012, industry experts said it was a clear move to rival Google’s email supremacy. Larry Magid, a consumer technology writer, trialled the new look before it was released to the public and applauded its “clean modern interface” that was “free of clutter and easy to navigate”. Other features he noted were the ability to mark messages as read, live chatting with Facebook friends, links to Twitter, LinkedIn, Google and Skype, and a design that clearly had smartphones in mind – unlike Gmail.

Since the rebrand, Outlook has made something of a comeback, Oakley tells me, but only really in workplace communication – not personal. “Whereas the majority of offices use Outlook for emails now, it’s true that its outdated reputation in the public eye has never, and probably will never recover,” he says. Safe to say, no longer exists.

And yet, I still use Hotmail – albeit with an email address that’s based on my actual name, rather than a teenage desire to seem edgy. For all its chaos, at least my inbox is reliable mayhem. Outside, the mess of the internet is much more unpredictable. There’s comfort in the familiarity of Hotmail, even if that does come in the form of nonsensical ads.

Speaking of, the Evisu sidebar has just changed – a Tiffany’s one now sits in its place. Perhaps it’s suggesting I propose to one of the bum models? Who knows. This is the kind of fun only Hotmail users can have.