On Monday, Microsoft brought the “Skyping” era to an end, officially shutting down the free-calling platform after a 22-year run that reshaped how people connected across borders.

The company announced the decision on February 28, giving users just over two months to transition to alternative platforms. 

Even the name “Skype” reflected the service’s early ambitions. Derived from the phrase “Sky peer-to-peer,” it hinted at how the platform connected calls through users’ computers instead of routing them via a central hub. That approach was groundbreaking in the early 2000s and set the stage for the app’s rise as a pioneer in internet calling.

The platform connected more than 300 million monthly users at its peak in the mid-2010s—roughly the population of the United States. But over time, it lost ground to a new generation of mobile-first apps like WhatsApp, Zoom, and eventually, Microsoft’s own Teams.

When Microsoft bought Skype in 2011 for $8.5 billion after outbidding Google and Facebook — its largest deal at the time — the service had around 150 million monthly users; by 2020, that number had fallen to roughly 23 million, despite a brief resurgence during the pandemic.

"Skype has been an integral part of shaping modern communications" said Microsoft.

"We are honored to have been part of the journey."

The company has been gradually shifting resources toward its Teams platform, which now serves over 320 million monthly users across business and personal accounts.

The fall of desktop communication giants

Despite revolutionizing internet communication in the early 2000s, Skype failed to adapt to changing consumer expectations and technological shifts. 

The voice, video and messaging app maintained its desktop-centric approach well into the smartphone era, missing crucial opportunities such as developing user-friendly mobile apps and integrating its chat and video-conferencing features with social media platforms that became standard in competitors like Meta’s WhatsApp and Facebook Messenger.

“Skype could not effectively modernize its offering, pricing or marketing strategy to stay on top of an increasingly crowded and fast-moving market,” says Alina Timofeeva, senior advisor in technology, data and AI.

During the pandemic, videoconferencing platform Zoom surged rapidly, capturing an additional 22.3 percent of the market, while Google Meet expanded by 20.2 percent. By early 2021, Zoom dominated the space with nearly half of all users, while Skype lagged far behind at just 6.6 percent.

Skype's two-decades journey from being a revolutionary technology to a digital relic reflects the story of many once-dominant early digital platforms.

Other desktop giants like Yahoo! Messenger have been shut down in 2018 after 20 years of service. During its peak in the early 2000s, the popular chatting platform boasted over 100 million registered users, having the second largest market share in the US market for digital advertising in 2012.

However, it eventually lost ground to more versatile, mobile-first messaging apps like WhatsApp and Facebook Messenger, which offered deeper social integration, better mobile accessibility, and more intuitive interfaces.

Yahoo’s lack of innovation, failure to keep pace with technological advancements or user expectations, and poor management decisions led to a lack of strategic direction for Yahoo Messenger. By 2017, Yahoo's core business revenue had decreased to $3.9 billion from $4.8 billion in 2013.

"Yahoo didn't pivot fast enough toward search, which Google does so well, or toward social, which Facebook does," said Laura Martin, New York-based senior analyst for investment bank and asset management firm Needham and Co.

While MSN Messenger (later Windows Live Messenger) disappeared in 2013, as the platform's user base shrank extravagantly from 330 million in 2009.

Microsoft’s $8.5 billion purchase of Skype in 2012 marked the beginning of the platform’s decline, as users were merged into the famous call app that ultimately shut down this week.

AOL Instant Messenger has also retired in 2017 after connecting 36 million users. In 2000, AOL's market value hit $125 billion, but by 2012, it plummeted to $1.75 billion, and between January 2011 and 2012, AIM's user base crashed by 64%, tumbling from 12 million to just 4 million and losing revenue competition to Gmail's Google Talk, SMS, and Internet social networks.

"The rise of Google and search, and Facebook and social, it's just taken a lot of advertising revenue out of the market," says Martin.

The rise of mobile messaging apps

WhatsApp in particular pulled ahead by designing from day one for smartphones and ensuring it worked the same way whether you were on iOS, Android or desktop. Its users now swap roughly 100 billion messages each day, nearly a dozen times the global SMS text messages.

This fundamental difference between mobile successors and desktop communication platforms lies in their underlying design philosophies. 

Desktop giants built their business models around stationary computing, while mobile platforms recognized that modern communication needed to happen anywhere, anytime. 

The lightweight applications, minimal data requirements, and intuitive interfaces of mobile messaging apps were purposefully designed for users who want to go wherever they wish, opposed to the session-based approach of traditional desktop platforms.

This shift mirrors a broader truth in today’s digital environment, where staying relevant depends on a brand’s ability to understand how people live, think, and connect.

“To stay relevant, brands must listen, adapt, and design for the whole person and not based on assumptions, but grounded in a genuine understanding of what customers truly need, using both behavioral science and data-driven insights,” Alina tells TRT World.