Cortana will now interrupt your Skype chats

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Microsoft’s virtual assistant Cortana has finally arrived in Skype. Announced at last year’s Microsoft Build 2016 event, the assistant’s integration was also previewed when the company released an overhauled, Snapchat-inspired version of its mobile messaging app this summer. But Cortana for Skype wasn’t ready at that time. Now, the feature is live, offering users in-context assistance during their chats, as well as the option to message Cortana directly to ask questions or get help with a number of other tasks.

It’s unclear why Cortana’s arrival in Skype took as long as it did, but the big Skype makeover could have contributed to the delay.

However, the idea to bring an A.I.-like helper to mobile messaging isn’t unique to Microsoft. Google’s Allo app is aided by Google Assistant, while Facebook Messenger has its own assistant, “M,” for example.

Similarly, Cortana will pop into conversations to offer suggestions based on the context of your chats. This includes “smart replies,” which are quick responses like “Yes!,” “Sure!”, and others, which you can select with a tap to save you from typing.

Cortana can also offer other input, like restaurant options, movie reviews, a good place to meet, a fact it knows the answer to, and more. Plus, the assistant can help with scheduling events and setting up reminders, which are then synced to your other devices where Cortana is enabled, like your Windows 10 PC.

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In addition, Cortana is being added to your Skype as a contact you can message directly, if you choose. In this case, you can chat with Cortana to ask it things like fact-based questions, the current weather, your flight status, stock quotes, restaurant ideas, directions, and more – very much like Google Assistant can already do.

While it seems like it’s now becoming table stakes to include an A.I.-powered assistant in mobile messaging apps, the real-world benefits of these integrations for end users are still a bit unproven. Too often, the suggestions interrupt and slow down conversations instead of adding value. And on multiple occasions, I’ve had to explain what those “dumb little icons” are that are getting in the way during a Facebook Messenger-based chat session. (“M” is suggesting stickers – and yes, that’s an exact quote from an annoyed friend.)

Smart replies on their own are a useful enough feature, as they feel more like an upgraded version of a keyboard app’s phrase suggestion, but many of the other A.I.-powered inputs are less than welcome. The problem is that these bots are butting in automatically, instead of being asked to contribute. Ideally, the user interface for these in-app assistants would be one where you press a button to ask for their help, rather than having them automatically add their 2 cents at every turn.

Microsoft says that Cortana began its rollout on Monday to iOS and Android users in the U.S. But this is not a switch that’s being flipped, so to speak – the rollout is gradual, meaning you may not yet see Cortana yet.