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Lets say I put 10 songs in the playlist we'll call them A thru J.
Lets also suppose that shuffle somehow miraculously plays them in alphabetical order.
After songs A thru D play and while song E is playing I add song Z to the playlist by finding it in the library, right clicking it and selecting "send to ... queue"
Song Z will play after song E is done and then the playlist will continue to play songs F thru J randomly but it will also play song Z again before stopping after all songs are played.
Songs A thru E do not repeat as would be expected, but song Z does.
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