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Okay all I did was plug my HDX via USB then drag a folder of music into the music folder via Windows Explorer. It immediately showed up and works fine on the music tab.
I say try again. There is no need to go through the cloud player I didn't need to.
Also my songs are all showing that are on the cloud. It could be your unit acting up as my first did with audiobooks but a factory reset fixed it right up.
If you keep having trouble use May Day that's what it's there for.
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