Turning my third-generation iPod into a flash-based device

iPod 3G in box
After successfully upgrading my iPod mini, replacing its failed 4 GB MicroDrive with an 8 GB CompactFlash card, I wanted to try to do the same thing for my older third-generation iPod. It’s my very first iPod, a 10 GB model purchased in 2003, and it has a great deal of sentimental value to me. Sadly, its internal hard drive stopped working sometime in 2009, and I never got round to fix it. By 2009 I had many other alternatives to listen to music on the go — I had the iPod mini, an iPod shuffle, and an iPhone 3G — so what was once my only iPod was now left in a box with its accessories. Every now and then I would take it out to recharge the battery (while feeling guilty because I was neglecting it), and every now and then I would search online for a new Toshiba hard drive of bigger capacity, but prices have always been a bit too high for my tastes. But recently I started considering the CompactFlash route, and when I stumbled on a very cheap 1.8-inch drive to CF adapter on eBay, I decided to go for it.

What follows is my personal experience, not a proper guide, so your mileage may definitely vary.

Disassembling the iPod to remove the hard drive

I followed the excellent iPod 3rd Generation Hard Drive Replacement guide by iFixit. Opening the iPod was hard and cost me lots of patience, attempts, a few tiny scratches on the iPod’s white surface, and a moment of panic when I thought I had broken something inside with the putty knife I used to separate the plastic front from the metal rear of the iPod. Follow the guide faithfully and pay special attention to the warning at Step 7 regarding the disconnection of the internal headphone jack connector.

Inserting the CompactFlash card

Unlike the iPod mini, for which it was simply a matter of swapping the MicroDrive with a CF card, in this case a 1.8-inch drive to CF adapter is needed. This is what I found and bought on eBay for a few Euros:

CF adapter

At first I thought I’d have trouble inserting it the right way, but I soon found out that there’s really no risk of making mistakes once you examine how the original hard drive connects to the drive connector. A small obstacle in my path at this point was a small plastic protrusion that enters a hole in the hard drive plastic edge near the 50-pin connector (evidently to help you insert the drive in the correct orientation and to align the pins properly). When I pushed the CF adapter down, this small protrusion prevented one edge of the adapter’s connector to insert all the way down. So I clipped it with a pair of small scissors, just enough to eliminate the interference.

Then I slid the CF card in. I was satisfied with the price and quality of the 8 GB SanDisk Ultra card I got for the iPod mini, so I purchased a 16 GB card of the same brand and model.

iPod with 16 GB Card

Connecting to the Mac and iTunes

Dealing with the hardware for this kind of upgrade hasn’t been particularly challenging. But as I was browsing the Web for information in the past weeks, I stumbled on a few different horror stories of third-generation iPods being especially fussy with this upgrade, some not recognising the card, some not being recognised by iTunes, some needing firmware modifications to work, and so on and so forth. I was ready to face troubles and complications, so after inserting the CF card and connecting the drive and headphones connectors, I didn’t close the iPod just yet.

Now, this generation of iPods was the last to be able to connect to Macs and sync with iTunes over FireWire. And being the first iPod with the long-lasting 30-pin Dock connector, it could effectively connect to Macs via FireWire and to PCs (and Macs) via USB. Tempted as I was to connect it to my Intel MacBook Pro over USB, I instead connected it to the same-vintage iMac G4 over FireWire. Like I did with the iPod mini, I just put the CF card inside without formatting it, assuming it was ready to use with a DSLR camera (therefore being preformatted in FAT-32 format).

Lo and behold, iTunes 10.6.3 on the iMac instantly opened and recognised the iPod and the CF capacity, but not the Serial Number and the Software Version, though it prompted me to update, telling me that “A newer version of the iPod software is available (version 2.3)”. (Also note “Format: Windows”)

IPod recognised 1

And the quirkiness begins

Naturally, I click on Update, and the (very fast) update process begins. iTunes downloads the iPod software version 2.3, copies it on the iPod, then — a typical final step in any iPod update — the iPod disappears from the iTunes sidebar, reboots, and remounts. iTunes warns about this with a dialog box that auto-dismisses itself after a few seconds. But the iPod doesn’t reboot. On the iPod’s display the message “OK to disconnect” appears. So I disconnect, then reconnect the iPod to the Mac. iTunes opens and warns that there’s an iPod with a corrupted drive connected (Uh-oh!) and offers to restore it and update the software. I let iTunes do its thing, and I’m presented with the same situation as before: the iPod should reboot (iTunes is telling me so) but it doesn’t. On the display, again, “OK to disconnect”.

I stop and think: evidently the iPod isn’t able to complete the update process by rebooting, so this time instead of disconnecting it, I manually reset it (by holding the Menu and Play/Pause buttons). It’s the right move, because after rebooting, under the Apple logo a progress bar appears. And since there’s now a CF card inside, the firmware update proceeds at an amazing speed. After 5 seconds, the Language Setup screen appears and the iPod is fine. I quickly go to Settings > About and all information shows up correctly: iPod name, capacity, available space, Software Version, Serial Number and Model Number. Success! But…

But now iTunes doesn’t see the iPod.

I reboot the iPod, nothing. I reboot the iMac, nothing. I disconnect and reconnect the iPod, nothing. Then I remember something I read on the Web… someone complaining that after the CompactFlash upgrade their iPod could only sync with iTunes via USB. So I take a USB cable and connect the iPod to the iMac via USB. iTunes opens and immediately recognises the iPod:

IPod recognised 2

Note that now everything appears correctly, and the Format is Macintosh.

Since I don’t have music yet on the iMac, before closing the iPod for good, I want to try copying some music on it, and to check if everything is okay when plugging the headphones. So I connect it to my MacBook Pro and — whew — no problems with the latest version of iTunes. As predicted, transferring music to the flash-based iPod is really fast, and once I plug in the first pair of earphones at hand, I can hear music just fine. However I notice an interesting detail: the iPod is not charging despite being connected to a high-powered USB 2.0 port directly. Quite baffling. I disconnect it, take a FireWire cable and connect the iPod to the G4 Cube. iTunes doesn’t open, but now the iPod is charging. So, was what I read in that forum true then — that after upgrading a third-generation iPod to use a CF card, it can only be synced over USB and only be charged over FireWire?

At this point I’m still utterly puzzled by the initial fact that, after updating the iPod to the latest software version, it stopped being recognised by iTunes over FireWire and just developed this behaviour. It’s not logical. In the end, what I’ve done is just replacing the hard drive with another ‘drive’, only it has flash storage. And then I have an idea. I connect the iPod to the MacBook Pro again over FireWire (like this: [iPod] → [30-pin to FireWire 400 adapter] → [FireWire 800 to FireWire 400 cable] → [MacBook Pro]). As predicted, the iPod starts charging but iTunes doesn’t recognise it. Then I put the iPod into Disk Mode manually. With this iPod, the procedure is as follows: you toggle the Hold switch on and off (set it to Hold, then turn it off again), you press and hold the Play/Pause and Menu buttons until the Apple logo appears, then immediately press and hold the Previous and Next buttons until the Disk Mode screen appears. (Source: Apple Knowledge Base).

As soon as the iPod enters Disk Mode, it gets recognised by iTunes as usual and it keeps charging!

And then another quirky thing happens: transfer speeds when copying music on the iPod are really slow. Not exactly USB 1.1 slow, but certainly slower than USB 2.0 or FireWire 400. I still haven’t had time to figure out this particular detail, and if I find something I’ll update this article.

Other minor quirks noticed so far

  • The iPod freezes every time I eject it from iTunes after syncing. For both iTunes and the Finder, the iPod has been ejected correctly, but the iPod’s display remains stuck on the “Do Not Disconnect” screen. Rebooting the iPod puts everything in order.
  • I’ve also noticed occasional hiccups: earlier today, I selected a song and playback wouldn’t start, as if I had pressed Pause right away. The whole interface was fully responsive and registered every button press, but songs wouldn’t start playing. Putting the iPod to sleep and waking it again solved that.
  • The battery icon appears to have become rather unreliable at displaying exactly how much charge there’s left (more on this below).

Battery life

When it was a new model in 2003, this iPod had an advertised play time of 8 hours. I used it very often back then: 2003 to 2007 were the years of most intense use. Its hard drive failed gradually, and in the last weeks before finally stopping working, it got quite loud and sometimes copying music was painful, with intermittent transfer speeds, aborted copies, and so on. What I had started noticing in these circumstances was that the iPod got unusually warm, and that battery life had decreased dramatically. So I didn’t expect much when I started my test this morning after leaving the iPod to recharge overnight.

All in all I’m not disappointed. The iPod played continuously for just about three hours (backlight set to its minimum setting, 2 seconds; frequent interactions to change album and sometimes the volume). Honestly, I didn’t think it would last this long, considering the little 630 mAh lithium ion battery is 13 years old.

I also didn’t think it would last that long because the battery icon in the status bar completely misbehaved during my testing. When I disconnected the iPod after leaving it on the charger all night, I expected to see a full battery icon. Instead it was at about 60%, and during playback it trickled down to zero in about an hour. I thought that’s what little life there was left, but the iPod kept going, kept going, and played music for two more hours with the battery indicator completely empty.


Working iPod
Overall, I’m happy with how things turned out. The 16 GB CompactFlash card and the adapter didn’t cost much, and I spent about three hours between the ‘surgery’ and the tinkering. It hasn’t been a smooth ride like with the iPod mini, but at least I have revived this third-generation iPod, the very iPod that started the ‘digital music revolution’ for me. The iPod I used as a boot drive to work from my 12-inch PowerBook G4 when its internal hard drive failed and I was waiting for a replacement. I’m glad to see this old buddy playing music again after being left in a drawer for seven years. I still can’t fathom why this specific iPod generation is so fussy when you perform the CompactFlash upgrade, but these quirks I’ve encountered are nothing insurmountable. Ultimately what counts is that the iPod is perfectly usable (by the way, I also put it in Diagnostic Mode, and it passed all the tests), and the occasional hiccup can quickly be resolved with a reboot.


16 thoughts on “Turning my third-generation iPod into a flash-based device

  1. Just did this mod on a broken hard drive 3G iPod 30GB I bought. I used the same compact flash to 50-pin adapter, a compact flash to sd adapter, and a 128GB SDXC card.

    I also bought a new battery for 4 bucks since the original battery was in there since 2003. Anyhow, I didn’t have any trouble restoring the iPod using Windows 7.

  2. One thing about that Y-cable with FireWire and USB that I just noticed is that it keeps the hard drive spinning even when the iPod is unmounted and off. The only way to avoid this is to disconnect the USB cable from the computer or maybe shutdown the computer as opposed to sleep.

  3. I’m having such a hard time with this mod. I just recieved my THIRD ipod 3rd gen in the post thinking that the other two I had tried it on had a bad logic board. And low and behold I’m having the same issue! The third ipod was definately working fine. I swapped out the drive and stucjin the adapter, cf to sd and 127gb sd card and now it isn’t recognized by either mac or pc, just like the other two. I’ve now bought 2 old ipod (one was mine from 2003), two cf adapters and a variety of cards. this is getting very expensive 😦
    I cant get the ipod into disk mode and it isn’t recognized no matter what I do.
    any tips?

  4. Just to clarify. This ipod model was never able to charge over USB. Only Firewire.

  5. @rgarjr
    do you have links on the parts you bought to do this upgrade? I Have a 40gb 3rd gen and would like to upgrade battery and to larger sd storage.
    Any video links on this particular upgrade? I’ve seen the you tube videos for 32 gb CF with the 1.8 drive to cf adapter, but not with the sd adapter and the sdxc card you installed. How does that work? just plug the sd adapter into the CF adapter, and the sdxc into the sd adapter?

  6. First, thanks for such a detailed post about this CompactFlash upgrade. This week I tried to do it myself, but I ran into a problem.

    Just like Riccardo, after the “Update” process is finished in iTunes, my iPod won’t reset itself and sits at the “OK to disconnect” screen. If I manually invoke a reset like Riccardo, though, the iPod reboots and then shows the exclamation mark/folder icon. The update process never completes. I have tried this over and over with many variations (see https://apple.stackexchange.com/questions/325953/why-does-ipod-3g-show-exclamation-mark-folder-icon-after-cf-upgrade), and I just cannot get the iPod to boot or complete the update.

    Anyone run into the same issue? Have any suggestions?

  7. Kirkman14,
    I have the same issue. I am using the iFlash dual adaptor with two 128GB cards though. I update to 2.3 via USB and it seems to take. Then the pop-up says plug into wall charger via firewire, but when I do that, and/or reset the iPod, I get the folder/exclamation mark too. Did you get anything to work yet?

  8. The website listed above on the July 4 post won’t let me leave a reply, so I’ll try it here.

    Greetz – I saw your post at wordpress. I have a couple of questions. Did your iMac have firewire 400? I have a 2009 MacPro that only has firewire 800 and I need to use an adaptor to connect via 400. Do you think that could be a problem? Second, when I look at my iTunes folder permissions they were already set to Read Only. however, I had “Staff and Everyone” as options instead of “Group and World” – but I am using 10.11.6 El Captian.

    One last odd thing – I tried to restore using a USB on a PC. It downloaded 2.3 fine and when I connected it to the firewire charger the apple logo popped up and then the status bar filled up as expected. However, then the apple logo came back and there it stayed for 45 minuted til I tried it all over again. That was the first time I had actually seen the status bar though. Now I’m back on the Mac with the apple logo and Folder exclamation point logo flashing back and forth again. Any thoughts? Thanks!

  9. For anyone finding this article who was also pulling their hair out trying to get this working. I think I managed to crack it.

    Like many others, I could get iTunes to detect an ipod and install the latest firmware, but it would not reboot and show the loading bar. When pressing the menu and play keys, it would reboot to a folder screen.

    When I had a look at the sd card, there was no partition table or folder structure. So it looks like nothing was being committed to the drive.

    Thankfully, I had the original HDD to compare to.

    fdisk shows 2 partitions. The 1st partition is where the firmware is stored, and the 2nd is where the data (folder structure) is stored.

    I used dd to copy the firmware from the HDD into a file: (dd if=/dev/sde1 of=~/ipod_firmware)
    Then manually copied the folders from /dev/sde2

    The next step was to manually create the 2 partitions on the sd card.

    The 1st was 40MB, of type empty, and set to active.

    The 2nd was the rest of the sdcard, of type FAT32 and also set to active.

    Both partitions were primary partitions.

    The final stage was to dd the firmware back onto the 1st partition and copy the folders onto the 2nd.

    Booting up into windows and running itunes, i was greeted with a “Welcome to your iPod” screen 🙂 .

    Using this method has no issues when disconnecting from the PC .

    The iPod 3rd Generation never charged through USB, so you will need to charge via firewire, you can however use USB to transfer your music, if your battery holds out.

    The downside of having 128GB of storage that nobody mentions; copying your 7000 tracks via USB will take all night 😀 .

    Sorry this isnt much of a howto guide. I didnt keep note of all my commands.
    I just wanted to let everyone know this is possible, it just not as easy as simple as first thought.

  10. @jaxter25 Hey I’m glad you found a fix! I think I’m having the same issue as you experienced, but my original HDD is toast. Is there a chance you have a copy of the firmware and file structure as it appeared on the original HDD?

  11. I was able to get past the boot loop by simply performing the iPod restore on a windows machine via a USB iPod cable during my upgrade to a 128Gb CF card with the same adapter.

  12. Jack Sprat, can you please explain in more detail exactly what you did? What version of Windows did you use? How did you go about it – through iTunes? What version of iTunes?

  13. So I got it to work! I will explain in detail what I did which is slightly different to the above comments. I used a virtual copy of Windows XP under VMWare and downloaded a copy of the Windows iPod Updater 2006-06-28. I then jacked my iPod into the computer through the USB cable. The software was really easy and gave me the option to restore the iPod. It took about a minute and then it came up and said it was ok to disconnect. I held the menu and play/pause button down and then I got it to reboot and it was all good again. The menu shows up – shows that it has 32GB of storage on it (I should have bought a 128GB) but it is formatted for Windows. So I am not totally sure as yet whether or not it will connect to my iTunes library on the Mac.

  14. I can confirm it does connect to iTunes and happily updates the music library, however it does require me to get another cable to charge and to sync to the iPod. Got mine coming in the mail…

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