If you’re anything like the staff at Macworld Towers, digital kit will slowly accumulate over time, until the point you could feasibly build an aluminium and white house from your various devices. If a lot of those old devices are iPods, you might at some point start thinking you’d like to get any synced music off of them, given that you might no longer have all of it in iTunes.
Only there’s a bit of a problem: throughout the years, iPods were designed to accept music sync only from iTunes, and the sending of music is a one-way process. This was likely to stop piracy, otherwise someone could have attached their iPod to loads of libraries, hoovering up files and dumping all the tracks on to their own Mac. If you’ve created a new library since last syncing your device, iTunes will want to wipe your device clean before syncing. (In our experience, it sometimes ‘helpfully’ tries to do this anyway.)
However, with some cunning workarounds, you can get at those old files.
How to get music off an old iPod
1. Launch iTunes without any devices connected, and in the Devices preferences, turn on ‘Prevent iPods, iPhones, and iPads from syncing automatically’, otherwise you might find iTunes immediately attempting to wipe whatever you happen to plug in.
2. Now connect all of your old devices, and check they’re all present and correct by clicking the little device icon in the toolbar. If you just want to see what’s on each device, select it from the depicted menu and then access its playlist from the Settings sidebar. Read: iTunes 12 review
3. Install and launch iExplorer. Note that depending on your security settings, you might have to open System Preferences > Security and click Open Anyway in the ‘Allow apps downloaded from’ section.
4. For any iPod that shows up (which should be any iOS device, and also hard-drive-based iPods like the iPod photo), you can select its Media Library in the sidebar. Select the tracks you want to save (or Cmd+A for all of them), click Transfer from Device, and choose whether to send them to iTunes or a Finder folder.
Read next: New iPod release date rumours
5. iExplorer also has an ‘auto transfer’ system, for saving only those tracks that aren’t already nestled in iTunes, but you’ll have to register the app in order to use that feature. Read: Move your iTunes library to a new Mac or external drive
6. If you choose to send your tracks to iTunes, confirm that they’re in the app once transfer has taken place, by checking your library and playing a few of them. If artwork is missing, you can get that back by control-clicking the cover and selecting Get Album Artwork. Read: How to tidy up your iTunes library
7. For iPod shuffles, we’ve found Senuti an effective tool to use. It costs $18.99, but the free trial’s good for 30 days or 1,000 tracks — and those old, tiny iPods rarely held anywhere near that number.
First, you’ll need to define what Senuti does with tracks it transfers — set a save location and decide whether songs should be automatically added to iTunes if you choose to copy them somewhere other than your iTunes library.
8. You’ll then see a window showing your connected devices in the sidebar. Select a Music folder and you’ll see the tracks on that device. Select those you wish to transfer and then use File > Transfer Songs or the Transfer button in the toolbar.
Be mindful that tracks saved to and rescued from iPod shuffles may be of lower quality than your other digital music, depending on the settings you used at the time. (iPod shuffles were in part designed for downsampled music, to fit more tracks into their meagre capacities. iTunes would optionally automate this process during a sync.)
9. Once all your tracks are back in iTunes, you can use the standard sync once again, which will wipe your device and then add back whatever tunes you like.