You may not be able to stream a playlist containing subscription tracks, even if your purchased tracks are in that playlist. You can try making a new playlist with your purchased tracks, and see if that works. Keep us posted.
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I'm requesting individual songs. Sometimes, rarely, they play. But usually I get the message of "That song's only available for Google Play Music subscribers, but try this random shit I picked out purely to piss you off".
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We recommend sharing a feedback report, including screenshot/logs, immediately after you get the error: ☰ > Help & feedback. It'll help our team to identify the issue. Also, you can try modifying the voice commands (i.e. play <song name> form my library) to see if that helps.
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