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I've done it before, but sometimes after a certain point it just breaks.
Explain please. What exactly stop working?
placing the track in the list where it's supposed to be
How you adding the tracks? via drag-n-drop in "to current place" mode?
This is how I add the track
I do have "To Current Place" mode too
In this case, the file will be added to end of playlist. But this setting is for drag-n-drop only.
I have it so the end of the playlist is first so that way I can listen to the newest to the oldest. It's adding it to the beginning though and I have to drag it all the way to the end.