When the preferences "Always replace playlist with opened files" is checked, it becomes impossible to add more than one file to the playlist. To test, open a file browser (Thunar in my use case), select a few audio files. Then, either right-click and chose "Open with Parole", or drag-and-drop them into Parole's playlist. In both case, only one of the files gets added to the playlist.
Indeed, I can reproduce and that is annoying. As a workaround for the meantime you can use the "+" button in Parole's playlist sidebar to add more files to the playlist while keeping that setting checked.
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