owen-tariq/podsync

PodSync is a free, open source app for Mac computers that lets you sync your music library onto a classic iPod, like an iPod Classic or iPod Nano. The author built it as a no cost alternative to existing paid tools, with the goal of keeping older iPod hardware useful without requiring a subscription or purchase. The main way you use PodSync is by dragging a folder of music from your Mac straight into the iPod's library shown inside the app, and it syncs automatically from there. It also supports movies, podcasts, and audiobooks, sorting each of these into the correct menu on the device the way the iPod's own software expects. If you drop in FLAC audio files, which classic iPods cannot play natively, PodSync converts them into MP3 or AAC format automatically while keeping the song information intact, so the files work on the device right away. Other features include checking for songs that are already on the iPod before syncing them again, and reading your iPod's play history so it can report those listens to Last.fm, a music tracking service, if you use one. The interface is built with SwiftUI, a native tool for building Mac apps, so it should feel consistent with other modern Mac software. To use PodSync you need a Mac running macOS 13.0 or later and a classic iPod such as an iPod Classic or iPod Nano. You install it by downloading a disk image file from the project's releases page and dragging the app into your Applications folder. Because the app is not signed with a paid Apple developer certificate, macOS may initially warn that it cannot verify the app, and the README explains a one line Terminal command to remove that warning so the app opens normally.