r/IpodClassic

Hi everyone,

I've lurked here for years but finally have something worth sharing.

About six years ago I got fed up with how painful it was to manage music on my iPod Classic. I went deep on every available tool, settled on Swinsian for library management, and ended up writing a sprawl of shell scripts to handle the bits it couldn't — especially around format conversion for large FLAC libraries. It worked, but it was never really what I wanted.

My background is iOS development, so eventually I just built something for myself. It did what I needed but was rough around the edges and never something I'd have shared. Then earlier this year I decided to properly sort it out and turn it into a real app — and that's what I want to share with you today.

ThirtyPin is a macOS iPod manager — a spiritual successor to iTunes, built with the Classic in mind.

What it does right now:

• Sync a local music library to your Classic

• Automatic format conversion — FLAC and other unsupported formats are transcoded transparently, with bitrate control so you can make the most of that storage

• Podcast subscriptions and syncing — episodes sync as proper podcasts, not just tracks

• Per-device sync profiles, useful if you run more than one Classic

• Full support for 6th and 7th gen, and the rest of the click-wheel family

The app will be free, with a one-time Pro unlock for advanced features. No subscription.

It's still in active development — I'm currently focused on polishing the UI — but I'm planning to open a TestFlight beta soon and will post here when that's ready. If you'd like to be notified, drop a comment or follow my profile.

Happy to answer any questions, especially from Classic owners who've run into the usual iTunes headaches.

https://preview.redd.it/1rpwp1ttcetg1.png?width=3172&format=png&auto=webp&s=2b663e529316a795fd61f724526270ac773cb787

I keep reading things about how the sound quality isn't good on the iPod classics. I currently use a iPhone 15 pro max and airpods so I'm expecting a bit of a drop in quality but if it's not major then I don't mind. I see listings for £80

Is it worth it over a modern MP3 player?