Microsoft introduced the personal assistant Cortana in 2015 when it released the Windows 10 operating system (and even earlier on Windows Phone). Just like Microsoft tried to get a fast start with Windows 10 by offering it for free, it attempted to push Cortana by integrating it deeply into the Windows 10 operating system.
Microsoft merged search with Cortana so that any user who used search was exposed to the personal assistant at the same time at first.
Windows 10 users could use Cortana for a variety of tasks, e.g. for answering questions, set reminders, or to control music.
The tight integration was not enough to establish Cortana as a competitor to Amazon Alexa or Google Assistant; Microsoft CEO Satya Nadella made the decision to reposition Cortana. Instead of playing catch-up with the two dominating assistants, Microsoft will now attempt to make Cortana a skill that is compatible with these devices.
The company integrated Amazon Alexa already with Cortana, and it plans to do the same for Google Assistant. Integration would improve Microsoft's reach significantly and users could integrate Microsoft products, e.g. Outlook functionality, with personal assistants that they have at home or work already.
The Verge reports that Microsoft would like for Cortana to become available as a skill of other digital assistants, like Microsoft "apps on Android or iOS".
Current Windows 10 Insider Builds confirm a change in strategy. Microsoft plans to split Search and Cortana in Windows 10 version 1903, the upcoming version of Windows 10.
Instead of launching the new version of Windows 10 with Cortana and search combined, Windows 10 version 1903 will have them split. Users who want to run searches can do so without having to deal with Cortana, and those who want to run Cortana can activate the personal assistant without having to deal with search.
Microsoft wants Cortana to become an essential skill, not only on Windows devices but also on mobile devices and smart speakers. Cortana could become an interface to control Microsoft services using non-Microsoft digital assistants.
Only time will tell if that strategy will be more successful, or if Microsoft will retire Cortana in the coming years.
I don't use personal assistants and have no intention of using them at this stage.
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