You can use the Drag & Drop function to move the files from iTunes to your Walkman.
Content Transfer for Mac is a software to transfer your music, video, photos, podcasts and playlists in an easy way. Find firmware updates, drivers and software downloads for NWZ-B183. Software and driver updates for your Sony product are available online. Using Sony software to transfer the music to your Walkman. If you do not have the latest version of the Content Transfer application already installed on your computer, it may be available through the Sony® Support website (for applicable models).
That is a great question! The good news is there is a link on the Sony website that has information and steps for syncing: How to transfer music from the Apple iTunes software to the Walkman player using the Content Transfer software. Thanks for reaching out to the Apple Support Communities! It sounds like you are wanting to know if you can sync your Walkman to iTunes. And MP3 players, including Apple iPod, Zune, Sony Walkman. ICoolsoft Sony Walkman Video Converter is a professional software which can convert video or audio files. Content Transfer Sony Walkman Download For Mac Walkman Software - Free Download walkman - Top 4 Download - offers free software downloads for Windows, Mac, iOS and Android computers and mobile devices.What are the functions of Hi-MD Music Transfer for Mac Ver.2.0? Auto print screen software. The Mac computer does not recognize the Walkman player when I try to transfer music content How to transfer music from Mac OS to a Walkman player. From the developer: Content Transfer for Mac software provides an easy way to transfer music, video, photos, podcasts and playlist form iTunes to the Walkman player.
The actual developer of this free Mac application is Sony Electronics Asia Pacific Pte Ltd.