Hi @Michael_Arones,
Thanks for your patience and persistence — you’re right that this was never a playback issue, and we’re sorry for the frustration caused by the earlier closure. We should have seen this through with you.
Reviewing your earlier responses, the most likely cause is that Roon is identifying one of the discs as a separate album because the CD-level subfolders repeat the full album title. In some cases, that repetition can interfere with how Roon determines that the discs are subordinate to a single album object during identification.
While Roon fully supports multi-disc sets stored under a single parent folder, it expects the disc folders themselves to be clearly subordinate (for example, CD1, CD2, CD3). When each subfolder repeats the full album name, Roon can interpret those folders as separate album candidates, which is how you can end up with Discs 1+2 grouped together and Disc 3 split off, even though the albums appear identical at first glance. Because of this, we generally don’t recommend structures like the one below:
Music/Miles Davis - The Complete Columbia Album Collection/
Miles Davis - The Complete Columbia Album Collection CD1/
01-01 Track.flac
01-02 Track.flac
Miles Davis - The Complete Columbia Album Collection CD2/
02-01 Track.flac
02-02 Track.flac
This layout often works, and it explains why many of your other box sets import correctly, but it does leave room for occasional misidentification — and this appears to be one of those cases.
If you haven’t already tried it, we recommend renaming the subfolders to a simple disc format:
Benny Goodman - The Birth of Swing (1935–1936)/
CD1/
CD2/
CD3/
After renaming, move the album out of the watched folder (or disable and re-enable the storage location), then reintroduce it so Roon performs a clean import pass.
Please let us know how this goes.