Hi This is one of the things about Windows 10 and Cortana in particular that drives me crazy. I've been using Cortana to play my music since she first showed up in Windows 10 Starting yesterday, when I say "Hey Cortana, Play my music." she says "Sure thing, shuffling your music." Then there is a short pause and then she says "Something went wrong, try again in a little bit." Now I have no idea what's going on, and this it the bit that drives me crazy, I have no idea how to figure it out. Because Cortana seems to have no interface to solve issues like this. It doesn't give me any clue why it does't play my music list, it doesn't say for example, "I can't find your music!", "I don't find a default music player" etc. I've checked and my Cortana play list plays if I click on it and select Play. I've tried setting my default music player to both Windows Media Player, which is what it's been using lately and to Winamp which is what it was using before I reinstalled Windows 10. But there seems to be no way to know what Cortana is supposed to do, no place to tell her where my music is located, (by default it has placed the Cortana.cpl file in my Music\Playlist folder which at least seems logical). Previously (before reinstalling) it played the music from my iTunes media folder. The thing is that I can't even see where Cortana is looking for the music or tell her where to look. Sometimes simplified is too simple. Mike I just remembered that iTunes updated in the last couple of days, I wonder it that has anything to do with it stopping working?