Unique problem using 2 Clips and iTunes

I burned a bunch of songs from iTunes to a cd. I then used iTunes to import the songs burned from the cd into .mp3 format.

Using Media Monkey, I transferred the songs to my first Clip no problem. When I tried to transfer those songs to a 2nd Clip in Media Monkey, I received an error “Problem with copying file” and it lists the path. Now, I tried the same process, but with songs that I didn’t transfer to the 1st Clip and still the same error. Is there a problem with my 2nd Clip?

Are both Clips in the same mode (MTP/MSC)?