The playlist definition itself should work assuming you have a playlist
named 'mylist' and it does contain at least one track which have play
count exactly 1.
Could it be that you have Custom Skip plugin installed and active so it
skips tracks when you play it, that would give exactly the behavior you
explain as it's active when playing something but not when using the
Test button.

If that's not it, could you try to enable debug logging of
plugin.sqlplaylist and plugin.dynamicplaylist in LMS
Settings/Advanced/Logging and then play the playlist and post the
server.log after you have tried to play it. You will find the server.log
file through LMS Settings/Advanced/Logging.


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