Hi @Christopher_Zapf ----- Thank you for the report and sharing your feedback with us, sorry to hear of the troubles.
Moving forward, we usually see this kind of behavior when Roon is unable to resolve the pathways in the playlist’s XML file. Can you please perform the following:
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Locate a single song that imported into Roon successfully that you know is also featured in the mentioned playlist.
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Verify it’s file path by navigating to the content in Roon and choosing “View file info” from the “3 dot menu” next to the track.
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Open up the iTunes XML and locate the same song that you’re viewing in Roon.
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Verify if the files paths match.
Let me know how it goes!
-Eric