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At Microsoft Build 2016, Microsoft announced plans to integrate Cortana into Skype (Microsoft's instant messaging service) as a bot to allow users to order food, book trips, transcribe video messages and make calendar appointments through Cortana and in addition to other bots.

A writer from Engadget has criticised the Cortana integration in Skype for only responding to very specific keywords, feeling as if she was "chatting with a search engine" due to the impersonal way the bots replied to certain words such as "Hello" the Bing Music bot brought up Adele's song of that name.

Cortana stores personal information such as interests, location data, reminders, and contacts in the "Notebook".

It can draw upon and add to this data to learn a user's specific patterns and behaviors.

In May 2017, Microsoft in collaboration with Harman Kardon announced INVOKE, a voice-activated speaker featuring Cortana.