Why is Siri unable to play Playlists on iOS 17.5?

Same here. It seems, the problem started right after updating to 17.5. Extremely frustrating. I rely on Siri commands to play/shuffle my playlists using CarPlay in addition to other scenarios. “Looks like Apple Music can’t play that” is always the reply.

I get the sense that Apple Music is somehow interfering with My Library. For example, I asked Siri to “Play (artist) in My Library.” It was a mishmash of songs by the (artist) in my My Library, immediately followed by the same song in Apple Music. (Won’t bore you with details on how I can tell the different sources.)

I have progressed with Apple Support from Representative, to Technician Reuben, who has been super reliable, and who is now communicating with Apple engineers. I have received several callbacks.

Again, extremely frustrating. But they are very much aware of the problem.

The latest: Technician Reuben called me this morning and also sent a corresponding email. Our issue has been further “escalated” but still no solution. From the email:

“Thanks for your patience. I received an update about your case. According to our escalations team on your behalf, a bug report has been filed for further review of the issue. This process could take days, weeks or even months before another response is received. 

The advice from our escalations team is for you to ensure that you keep your iPhone 15 Pro software update, as the response from engineering can come as additional troubleshooting steps to complete, a software update or a new article with instructions on how to proceed to resolve the Siri unexpected behavior.”

I wish I could be sharing a definitive fix, but it looks like it could take a while.

I've been experiencing this same issue exactly as you stated. I'm hoping someone can help.