Something that I've become aware of recently is that if I have an album or tracks in the queue, other albums or more tracks appended to the queue don't always play when the original selection finishes and have to be manually started. I can't pin it down to any particular sequence or logic.
I'm doing this all the time - and DSTM does exactly this, too. What kind of content are you playing? Did you check your server.log for any hint about an issue?
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