Cortana should...

Cortana unprompted interactions (in a non-intrusive way)

I'd like to see back and forth conversations, and unprompted interactions with Cortana using the functionality that she already has for text messages:

If your notifications aren't silenced, on vibrate, or in quiet hours...

Cortana: "Hey, [name]? / Excuse me, [name] / etc."

•Cortana listens for "Yes?" "Yeah?" "What's up, Cortana?" etc.

(If she doesn't hear an affirmative response, conversation stops. This is the polite, "Are you available?" check to avoid bugging you when you're busy... similar to how a real assistant would check.)

Cortana: "You know that thing you asked me to remind you about earlier? Don't forget to call your wife about XYZ tonight."
or "You'd asked me to track ABC subject for you. I found something interesting about it. Do you want to hear about it?"

•Cortana again goes into listening mode, looking for things like, "Yeah, read it" or the other similar prompts we get with text messages now.

•If "Yes." Cortana reads subject of news item, update on plane flight, etc.
•If "No." Cortana says "OK, it will be on my list for you when you check later."
•If "Right, call my wife please." Cortana starts the call, or performs other app functions depending on the context of the reminder.

I think that would make her feel a lot more like a real assistant. You can use the same functionality we already have for text messages, just include a very short, polite "Are you available?" prompt in front of other reminders and things she's tracking for you (and allow the feature to be turned off, or limited to only prompting every X number of hours for news/subject updates).

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