Problems transferring files with iTunes on Mac

I am starting to use a brand new Clip Sport and I am having difficulty transferring songs onto my device using iTunes.

When I open iTunes the device does not seem to be recognized at all.  There is no indication that the Clip Sport is a device that songs can be transferred onto.

There does not seem to be a problem with the computer itself recognizing my device.  When i use my Finder on my Mac and I connect the Clip Sport, I can see that the player appears under Devices.  Through this method I am able to transfer songs onto the Clip Sport that happen to not be in iTunes.

Any assistance would be greatly appreciated.

Have you tried to open a window showing the content on the Clip Sport and use drag and drop from iTunes to that window?

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