Skype, once a pioneering VoIP service, has been relegated to a forgotten relic of the pre-mobile era, a casualty of Microsoft's failed efforts to integrate the service into its ecosystem. The company's $8.5 billion acquisition of Skype in 2011, its biggest-ever deal at the time, was meant to help Microsoft compete with the rise of the iPhone and other mobile devices. However, over the past 14 years, Microsoft dropped the ball again and again, failing to address fundamental issues with the service and ultimately losing ground to competitors like Zoom, WhatsApp, and FaceTime.

In the early days of the Skype division at Microsoft, the team was focused on building a new version of Skype for a touch-friendly version of Windows. However, as Skype increasingly turned its focus to mobile, problems with overhauling its aging peer-to-peer infrastructure started to emerge. Microsoft began migrating Skype users to its Messenger platform in 2012, which previously helped power MSN Messenger, to improve the ability to send chat messages and pick up calls on multiple devices. This transition lasted years and resulted in many bugs, including calls, messages, and notifications repeating on multiple devices.

Despite the issues, Microsoft continued to add features to Skype, including emoji and a radical redesign in 2017 that didn't go down well with users. The company was forced to redesign Skype once again in 2018 and walk back the Snapchat-like changes, but it was too late. WhatsApp, Messenger, FaceTime, WeChat, Line, and Telegram had already become entrenched, offering easy video calls and reliable messaging. As a result, Skype was relegated to a forgotten relic of the pre-mobile era, with Microsoft ultimately deciding to replace it with Teams in May.

There's no longer a Skype division inside Microsoft, and the remaining team has been combined with the Teams org to work on future features of the app. While Microsoft might have stumbled with Skype, the acquisition helped bring Teams to life in 2016, and it even acted as a bridge to transition business users from its Lync enterprise messaging software to Skype for Business and, eventually, Teams.

However, the issues that plagued Skype are still present in Teams, with users complaining about the complexities of switching tenants, or just because they're using a personal Microsoft account and Teams gets confused. The messaging part of Teams is still very basic, although Microsoft is looking to address that with threads and combined chats and channels soon. There are plenty of areas for improvement with Teams, and while the faster and redesigned client is a good step in the right direction, it should be the foundation for bigger changes.

The Teams complaints are growing, and Microsoft will need to address them a lot faster this time if it wants to avoid another Skype situation. As the company continues to push ahead with its AI initiatives, including the launch of a new AI accelerator and agents for sales, it's clear that Microsoft is still learning from its mistakes with Skype. Whether it can apply those lessons to Teams remains to be seen.