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Hello there, Alfatom!

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. 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.
IMPORTANT:
- 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). Software and driver updates for your Sony product are available online.
- You can also install the application from an included CD (if applicable) or file on your Walkman® player (if applicable). Check your manual for more information about installing the included software. Manuals, Specifications and Warranty information for your Sony product is available online.
- The Content Transfer (Windows version only) installation requires the Windows Media Player 11 software.
- It is recommended to use the Apple® iTunes® software version 9 or later with the Content Transfer version 1.3 or later software.
Follow this procedure to transfer DRM-free iTunes Plus® files or other files not containing DRM, such as MP3 files, to your portable player using the Apple iTunes software:
NOTE: A procedure is available to confirm that the files you are trying to playback are DRM-free.
- Start the iTunes software.
- Connect your portable player to your computer.
- Start the Content Transfer application if it did not start automatically.
- Locate the song in the iTunes software.
- Drag and then drop the song into the Content Transfer application.
Cheers!
Sep 19, 2016 12:37 PM
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The highest quality Sony Walkman is a luxury portable high-res audio player with Android streaming apps, a premium build and excellent sound. Most users prefer the Walkman, which offers outstanding detail, luxurious comfort, and impeccable build-quality. The Walkman is compatible with a wide variety of audio file formats, including FLAC, Apple Lossless (ALAC), and AIFF, as well as “lossy” formats like MP3 and AAC.
But many Spotify users ask 'Can Sony Walkman play Spotify?' The answer is yes, but not through Spotify app. Spotify requires an internet connected device with the ability to run a Spotify application. Sony Walkman is not in the compatible list. Then how to listen to Spotify music on a Sony Walkman? Most Spotify fans want to download and transfer Spotify music to their Sony Walkman and enjoy high quality music when they are running or traveling without internet connection. To solve this problem, you should use a third party converter to unlock the Spotify DRM and transfer Spotify music to Sony Walkman supported format like, MP3, AAC, FLAC…
In order to transfer Spotify music to Sony Walkman or other MP3 players, you should remove Spotify DRM and convert Spotify to mp3 first. After comparing several Spotify to mp3 converter, we strongly recommend Ondesoft Spotify Music Converter. With it you can get rid of the restriction of DRM, and sync your playlist from Spotify to Sony Walkman. It helps you to remove DRM from streaming Spotify music and save them as DRM-free MP3, M4A, WAV or FLAC audio files. What's important, it preserves 100% original Spotify music quality and keeps all ID tags and metadata information to output DRM-free songs.
The following is a step-by-step tutorial about how to convert Spotify to MP3 and transfer them to Sony Walkman with Ondesoft Spotify Converter.
How to paly Spotify music on Sony Walkman?
1. Run Ondesoft Spotify Converter
Download, install and run Ondesoft Spotify Converter. Please make sure you have installed Spotify app on your computer.
2. Import songs from Spotify to Ondesoft Spotify Converter
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Click the Add Files button, then drag Spotify songs, playlists, albums from Spotify app to the interface. If you are using Spotify web player, copy and paste the link to the bottom left area. Then click the Add button to import all Spotify songs you’d like to convert.
3. Choose output format
Click the Options button, you can choose the output format ( MP3, M4A, WAV and FLAC), bitrate (128kbps, 256kbps, 320kbps and 512kbps), sample rate( 22050hz, 44100hz and 48000hz) and output folder as you prefer.
4. Start Converting
When finish above settings, click the Convert button to start the conversion. After the conversion, click the History button, you will find all converted DRM-free Spotify songs.
Step 5 Transfer Spotify songs to Sony Walkman
Transferring music to the Walkman is as simple as connecting the device to your computer with the included USB cable and dragging and dropping the output folder into the Walkman’s “music” folder.
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