How to make Cortana play my newly created playlist on shuffle

I have created a playlist called Hiphop. How can I ask Cortana to shuffle n play the tracks. As of now when I say play hiphop it starts with the very first song in the playlist.

It's been a while since I raised this question. Can someone please reply?

I don't have a specific answer for your question,but I can say that Cortana is useless at music shuffle.plays the same track every time I try it 9 times out of 10.then other times it plays one of two other ones.Would be cool if it actually worked.i have over 100 tracks

I think the shuffle problem is fixed now. Any update on how to make Cortana play a playlist on shuffle mode?

I say to Cortana "play MY GO TO playlist" and it does. My playlist name is "MY GO TO". I have no problem with it.

I dont know what exacly triggers it, but sometimes I manage to get Cortana to shuffle my playlist. I usually say "play my X playlist, shuffle", sometimes she shuffles sometimes doesnt.