I think I'm beginning to figure out what's wrong. When I import the file from "Playing Now" it isn't tagged to show artist, album, track or song title - for some reason I'm having to manually add those tags even though most of the rest of the songs on the same album are correctly tagged.
Yes. When you import via one of these mechanisms:
* Import via drag-drop from Windows Explorer or the Finder
* Import from Playing Now by right-click > Import.
* Import via Automation Commands (generally, unless you run Auto-Import via automation)
Then MC imports the file completely "clean" and does not do the normal processing it does on the file, unlike other regular Import methods. This is an "escape valve" you can use if MC's normal automatic parsing is causing problems when importing a file. For more info, check out the wiki page:
http://wiki.jriver.com/index.php/ImportHowever, you can force MC to pick up the tags from the files themselves, even if they were already imported in this way. Simply select the files in question and do:
Right-Click > Library Tools > Update Library (from Tags).
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