If you're unable to transfer purchased music from iTunes, consider the following: Cloud-based Music: Verify if your music is stored in iCloud rather than on your device. Look for a cloud symbol with a downward arrow next to the track in iTunes. Downloading from iCloud: Click the cloud symbol to download the music file to your computer's hard drive. This step is necessary before transferring music to your H2O Audio device. Transferring Music: Once downloaded, you can drag and drop or copy and paste the music files into your device's memory. Further Assistance: If problems persist, our customer support is available to help via chat, email, or phone. For any additional questions or support, don't hesitate to contact our customer service. We're here to ensure your H2O Audio experience is seamless and enjoyable.