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Do I need to check every one of those album folders and load a cover art image into each?

Yes......

ROON simply don't write tags. If you cancel your subscription or use the files outside ROON, all the ROON supplied meta data is gone.

Your best bet is to point any media player to the files.
It will start to scan and, like the Eversolo, will find out that artwork is missing.
Select all these files and do a internet lookup. My preference is to embed the artwork in the file.
Musicbee has an option to download artwork. I expect Audirvana, MP3tag, etc can do this as well.


The Well Tempered Computer

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