Although Sony's Walkman MP3 products and Apple's iTunes were not designed to work together, there are ways, and software packages, that allow you to synchronise them. The ability to do this allows you, with some limitations, to load your favourite songs and videos from your iTunes library onto your Walkman without having to go through the time-consuming procedure of importing these songs and videos all over again.
Open iTunes by clicking on the icon in your task bar. Insert an audio CD containing music you want to add to your Walkman, if you don't already have it already in your library, and click on "Yes" when "Would you like to import the CD [Album Name] into your iTunes library?" appears in a box on the screen.
Install and open the Content Transfer Software that comes with your Walkman.
Click on "Music" tab in iTunes and select the songs, or videos, you want to sync with your Walkman. Click and drag these songs/videos into your Content Transfer Software; the software will now automatically sort and label your music collection.
Plug your Walkman into your computer's USB port using a USB cable; the files that you dragged and dropped into the Content Transfer Software will automatically transfer to your Walkman.
Close iTunes. Disconnect your Walkman from on screen first, using the "Eject" tab on your Content Transfer Software. Unplug the USB lead from your computer.
Select multiple songs, or videos, to drop into the Content Transfer Software at once by clicking on a song, or video, while holding down the Tab key and then clicking on a file farther down the list.
Do not disconnect the USB lead from your computer's USB port, or from your Walkman, without first ejecting it through your software program. Failure to do so could lead to lost data.