You may have to delete a few tracks for it to work. This is the note from the download page.
Note:
To perform this update, the WALKMAN needs to have at least 50MB free space.
Best of luck.
When I've had problems like that in the past with other models, I found updating the firmware cured it. You can download it from here, http://support.sony-europe.com/dna/wm/nwvp/nwvp.aspx?site=odw_en_GB&m=NWZ-E438F .
Hope it works for you.