Regensburg, Germany - 2022-01-06
iPod Classic
macOS 12.1 Monterey
Windows 11


I'm not responsible for anything that happens to a device while following these steps. Rockbox is an Application created and hosted at Read about the risks in their FAQ. This guide comes with absolutely no guarantee. Follow this article at your own risk!


My iPod Classic 6th Generation has been upgraded with an 128GB Micro SD and a 3000mAh battery. After following a lot of guides for Catalina, recompiled 64-Bit Binaries of Rockbox and having no success with any of these methods i tried it myself.
This is how i got Rockbox onto my iPod on a Macbook Air with an Apple Silicon M1 Processor using macOS 12.1 Monterey

Steps overview

  1. Kill Finder Process (important)
  2. Start Windows VM (Parallels)
  3. Connect iPod Classic
  4. Select Windows VM as target for iPod
  5. Launch Rockbox 5.1 Install Bootloader 5.2 Install Rockbox files


  • A Windows VM with x86 Application Support (e.g.: Windows 10/11 for ARM)
  • Rockbox installed in Windows VM Download at

Let's Go!

Since Catalina, iTunes is now integrated into Finder, which caused most of my problems. When in DFU Mode, Finder would prompt me to restore my iPod and locking it in an state where it could not be mounted to the VM.
If you want to start Finder again, you can do so at any point by using CMD + Space and typing Finder, followed by an Press on the Enter key. This will however launch the iTunes Service and lock the iPod (until you remove it).
Step 1 - Press CMD + Space and open Activity Monitor.
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Step 2 - Filter top left for finder - Select finder - Press Kill-Button
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Step 3 - Press CMD + Space and open your Windows VM.
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Step 4 - Connect iPod and select VM as Target - Tick Devices -> USB & Bluetooth -> Apple iPod
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Step 5 - Start Rockbox Utility
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Step 5.1 This one is debateable and seems counter intuitive. My installation would always fail when installing the bootloader and Rockbox itself at the same time. Only success i had was when first installing the bootloader (rockbox will boot into an error) and then install rockbox itself. You can try different variations. This one worked for me.
  • check in activity monitor that there is still no finder process
  • When entering DFU Mode, Parallels will ask you where to mount your iPod. Select your Windows VM! If that fails and your iPod is mounted in macOS, repeat immediatelly Step 4 (DFU iPod is an different Device), then Step 2 and then repeat this Step.
  • use Autodetect for your iPod Classic
  • Uncheck everything but Bootloader
  • Click Install
  • Follow on Screen Instructions
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Step 5.2 Don't panic, after the previous Step finished successfully, you will be prompted with the following error.
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Thats fine, we only installed the bootloader. We can now return to Rockbox and select the other checkboxes. But make sure to remove the tick from bootloader! After i flashed the bootloader again i would be prompted with the same error again. So make sure to unselect bootloader.
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Afterwards you will be greeted by Rockbox. Hold Select + Menu until the screen goes black, then keep only Menu Pressed and you will reboot into the original Firmware. If you want to boot back into Rockbox you can Hold Select + Menu until the screen goes black and Rockbox will be booted.
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If any Step fails, dont panic. Repeat first Step 4 and afterwards Step 2. Only then reconnect the iPod.
Dominik Stötter
Developer by day. Photographer at golden hour. Occasional word wrangler after dark.


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