Microsoft is in the process of rolling out a new integration between their personal assistant, Cortana, and the Skype messaging client. The new integration essentially makes Cortana a chat-bot inside of Skype, allow it to give you suggestions for replies to messages, get weather and news information, as well as facts and other information. In order for it to work, you have to give Cortana various permissions for Skype and since it is rolling out now, not everyone is seeing it just yet.
If this sounds familiar as an Android user, it should. Essentially Microsoft is replicating what Google has done with Allo and Google Assistant which, for Windows 10 PC users and those who are heavily in the Microsoft ecosystem, this is great news.
As indicated earlier, the update is rolling out now and it appears to be on the slow train. It does appear to be rolling out for Android and iOS users but it is only in the Preview (beta) version of Skype on Windows 10. There isn’t much you as a user can do at this point other that wait for it to pop-up in your Skype app once it hits your account. Just make sure you have the latest version of the app as well as Cortana on your phone.
The integration of Cortana and Skype has been a long time coming and one that Microsoft indicated would be coming this year.