A childhood friend of mine got an iPod in 2004. It was a third generation model with a mind boggling 40 gigabyte hard drive. This was incredible at the time – I had just gotten my first MP3 player with very modest 128MB of storage, a NAPA PA28. Despite its minuscule storage size, it was still exciting to use at a time when portable CD players still reigned supreme. But my friend’s third gen iPod stayed with me as the definition of premium music player for years to come.
Over the next few years, I got a few more portable audio players, each with more capacity, but none with the style and convenience of an Apple iPod. In 2005 I got a 5GB Olympus M:Robe MR-100. This stylish device was neat, it had the look of an off brand iPod mini but it didn’t look cheap (it also wasn’t cheap). Unfortunately, the smooth glass surface was predictably sensitive to drops and scratches, and its tiny hard drive died after one too many falls. I replaced it with a Creative NOMAD Jukebox Zen Xtra (30GB). This was an ugly, brick like device that used a regular 2.5″ hard disk. The build quality was cheap, but it was less prone to damage. Looking back, it seems like every consumer electronics company was making MP3 players at the time, and most of them were similarly unremarkable. But this device didn’t last long either – by 2008 I finally replaced it with a 120GB iPod Classic, a music player that I ended up using for a long time, well into the streaming era.
At some point though, after I was already using my iPod Classic, my friend gave me his third gen model. Its hard drive had (expectedly) died as well, and he knew I liked to tinker with things. I held onto it.
In 2011 I discovered Mark Hoekstra’s blog Geek Techique. Mark sadly passed away in 2008, but his family and friends keep his website online to this day (as of November 2024 you may get a certificate error, but the website is still up!). Mark was a tinkerer, and his blog is full of fun and interesting projects, many of which anticipated the retro storage conversions from hard drive storage to flash solutions that are so common these days (like the blueSCSI). One of these projects was the manually wired Compact Flash card adapter, meant to be used with an iPod instead of a hard drive. Mark may have been the first person to do this – it seems that such adapters weren’t a mainstream thing before then. While there are references to him trying to commercialize this project, he sadly passed away soon after. Cheap CF to 1.8″ IDE adapters became available to buy online by third parties before long. I still visit Geek Technique from time to time, and I’m happy that Mark’s work lives on, on line. I wrote about his blog earlier this year on Mastodon, and a few years ago on twitter (archived post).
Prompted by this discovery, I decided to attempt to repair my friend’s third gen iPod. I got one of those cheap adapters on Amazon, but I never got it working. Frustrated, I replaced the 1.8″ drive with a used one. I seldomly used this iPod over the next decade, and the replacement hard drive still works. In 2020 I briefly attempted to get the Compact Flash adapter working yet again, while I was restoring my black Macbook (2006). This attempt also failed, but I did document using the third gen iPod to natively download podcasts through iTunes. As of 2024 this is almost impossible, because virtually every RSS host requires modern SSL, which is no longer supported by old versions of iTunes that did support iPods and podcasts.
Fast forward to earlier this year. Prompted by the resurgence of interest in pre-streaming music players like iPods and Walkmans, I took out the old third gen iPod once again. I scoured the internet once more, looking for documentation on successful flash conversions. I found the testimonials lacking — almost none went into technical detail, and they primarily dealt with setting up compatible versions of iTunes to successfully restore and format the card with iPod firmware. I already had a good version of iTunes — I used it without issue to manage the hard drive in my iPod.
I was using the same CF to 1.8″ adapter I got in 2011. I tested continuity countless times, and I couldn’t find anything electronically wrong with it. As soon as I put it in, the iPod wouldn’t start at all, stuck on the Apple logo. I tried tons of CF cards as well as SD cards in a CF adapter. I could not even get to the point of attempting a firmware restore. I attempted using different iTunes versions and computers to try to get it detected. Nothing worked.
Then I decided to try one thing that I hadn’t done before – I got an actual FireWire to 30 pin cable, which is needed to restore an iPod 3rd gen from a Mac (Windows can do it from USB). I used OSX Tiger because later iTunes can’t use FireWire. I had no luck at all.
Finally, I actually managed to get some sort of recognition, but not in the way that was actually useful. Through bizarre trial and error, I discovered that if I format the SD card inside a CF adapter to an HFS+ volume, then don’t put it in yet, but turn the iPod on via battery, and wait for the folder icon to appear. I would then connect FireWire, followed by a quick insert of the CF adapter and then the iPod would actually switch to disk mode and actually get recognized by my Mac!
But this was still not working. The Mac would mostly freeze, and the few attempts at restoring failed. I finally gave up on the adapter I bought 12 years ago, and I ordered a new one for $7. It still made no sense to me why the adapter would be the cause of the issue, but I had to try something else.
I got the new adapter. It was the exact same design, with identical connections and I had no idea why it would work any better. However, unlike the first adapter, this one actually showed me the folder icon immediately without my weird trick!
Attempts at restore failed, again. But I kept going. I did have an image of a properly formatted drive, so I copied that over to the SD card with dd.
$ dd if=ipod.img of=/dev/sdb status=progressI had actually tried this earlier, so expectations were low. Except this time, the iPod happily booted! However, dd’ing a 20GB hard drive to a 64GB SD card left lots of empty space.
Since I couldn’t use iTunes to restore, I backed up the contents of the storage partition, then I used gparted to delete it and create a new one, this time extending it to full size of the 64GB SD card. Finally, I copied the files back over. The iPod and iTunes didn’t mind. This was the partition table after this was all done:
Once this was done, I was able to sync the iPod with no issues over USB. This decade long repair did leave me with some unanswered questions. I know that the original adapter must have had some kind of fault. Maybe there was some undetected short or something that made it impossible to start booting with it, but if you engaged it later it would function. Who knows!
The issue with restoration still bugs me. I don’t know why my attempts to restore via FireWire kept failing, even with a good adapter. It’s possible that in the end it came down to a specific version of iTunes and OSX version. My solution of just dd’ing a known good iPod 3rd gen hard drive and then recreating the storage permission was a very brute force way of getting around this problem. Paul Rickards recently did a much more elegant iPod 3rd gen restoration where he recreated those partitions manually, and then copied over iPod firmware with dd.
It’s important to note that I had different experience with different 30 pin cables. I was unable to successfully use the 3rd party FW cable, nor the Apple USB/FireWire combo Y cable. The USB in the Y cable worked sometimes, but not consistently. All my successful syncs were done using a regular 30 pin USB cable. Whether something is broken in those FireWire cables, I can’t say.
In any case, my iPod has been reliably working for months now, and I’ve been using it as my primary portable music player. I barely use my smartphone to listen to music any more. The iPod lets me listen to exactly what I want – no more random Spotify versions of songs that I know should sound different, or unintended switching into “artist radio” mode when I want to listen to an album. It also helps me stay off my phone when I’m riding the train or walking. It’s a strange and frustrating thing when you have to use older technology to keep yourself from engaging in compulsive behavior caused by contemporary tech. The only feature I really do miss is the ability to load up podcasts. The third gen iPod was one of the first portable players actually used for podcasting, first with dedicated programs like iPodderX and later with iTunes once Apple implemented the functionality, helping give podcasting the name it still holds. I could build an SSL proxy server to help with this issue, but I haven’t had the time yet.
Which lastly brings me to library management. I’ve been using my 2006 Macbook to manage music on my 2003 iPod. I like how it makes the process intentional, and I usually update music every few months. The third gen iPod actually does get recognized by macOS 15 though, and I could theoretically use my brand new Mac Mini to manage it! Apple moved iPod management into the Finder after it sunset iTunes, but my experience has been mixed. For now, my iPod is still managed by its contemporary Macbook.
Useful files: