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I saw in a recent changelog for Groove that it was supposed to start being able to respond to Cortana requests to play a genre if you have a Groove pass. But I still can't get it to play a specific artist through Cortana (if it makes a difference I don't have a pass). "Groove music play Adele" results in pulling videos from the web instead.
You don't need to say Groove before it, just "hey Cortana, play ______". It will play from anything you have in Groove, if it can't find it then it asks you to buy a music pass. You'll want to make sure the metadata (specifically artist) is good for your own music, otherwise it won't pick it up. If the artist is spelt wrong or missing, it won't find it, and it'll ask you to buy a music pass.
Thanks! I see that in the tips now. What's strange is that she asks for a subscription if I ask for a specific album (which is on the device and I own) but not if I just ask for the artist. Also, it doesn't actually launch Groove, just plays it as background, so it's harder to do followup things like turning off shuffle.
Try putting an album you own in OneDrive instead of local and then ask for her to play it.