Always had my ipod classic to manually transfer songs from itunes. Have over 4000 songs on my ipod now. Not on itunes. Itunes is recognising my ipod but every time I try to manually move the music across to the ipod nothing gets transferred and itunes won't locate the songs anymore (exclamation mark in circle next to each song on itunes).
iPod classic
See Recover media from an iPod to reclaim any media on the device that isn't in your library.
See Backup your iTunes for Windows library with SyncToy to backup the library.
See Corrupt iPod Classic to check the health of the iPod.
Once everything that you want on your iPod is secured in a library and backed up see Use iTunes on your Mac or PC to restore your iPhone, iPad, or iPod to factory settings - Apple Support to wipe the device and then reload it.
tt2
itunes won't transfer my music to ipod classic and deletes all the songs
