Move Current iTunes Library to Mac OS 9 / iTunes 2.x and 1st Generation iPod

Moving iTunes 12.x Library

In our last post, we looked at the revolutionary new first generation iPod, the public’s reaction to it, its competition and finally a bit about iTunes 2.x. In keeping with Steve Job’s vision of the Mac as the home digital hub, the iPod was supported by iTunes 2.x. While the iPod was a complete and standalone music player, it required iTunes to load music onto it and to manage its more complex functions.


ITunes 2.0.4 was the current version of iTunes when the iPod was released. I decided to try moving my current iTunes music library over to iTunes 2.0.4, and then use itunes 2.0.4 to load a portion of that library onto the 1st generation iPod I reported on in the last post. In the end, I accomplished this successfully and this blog post reports on the process I used to accomplish the transfer.

My current music library is hosted on my late 2011 27” iMac, running Mac OS X Mavericks and iTunes I started the process by copying my entire iTunes folder from my iMac out onto a common file server that is visible to both the iMac and the target machine, a Power Mac G4 Cube running Mac OS 9.2.2. Here at the Happy Macs Lab, we have a 2.3 GHz Power Mac G5 under Mac OS X 10.4.11 Tiger (my first personal Macintosh, from back in 2006) acting as the common file server, and it was to a shared folder on this machine that I copied the 27 GB or so of my music library to.

If you are wondering where to find your iTunes folder, it is in your home folder, inside the Music subfolder, and is simply called “iTunes”.

From the file server, I copied the full iTunes folder onto the PowerMac G4 Cube, and renamed it simply “MyMusic”, so as to not potentially confuse an early version of iTunes with a music folder named “iTunes” that it was not managing. I don’t know if this step was necessary or not, but I did it as a precaution.

MyMusic Folder 2

Next, I opened the MyMusic folder and deleted all the iTunes metadata files, and a few more besides, so that the folder contained ONLY music and nothing else. The deleted files included:

  • iTunes Library Extras.itdb
  • iTunes Library Genius.itdb
  • iTunes Library.itdb
  • iTunes Music Library.itdb
  • Mobile Applications
  • iPod Games

With that done, I started iTunes 2.0.4. I selected “File->Add to Library…” and then used the resulting file browser window to navigate to the folder containing the MyMusic folder. I highlighted MyMusic and pressed the “Choose” button on the lower right of the window. The import started and an “Adding Files” dialog was displayed, showing the progress of the import. Depending on your CPU and the amount of RAM you have, this will take a greater or lesser amount of time. In my case, with the Power Mac G4 Cube upgraded with a 1.2 GHz G4 CPU, and a full complement of 1.5 GB or RAM, it took about 5 minutes.

iTunes After Import

At this point, I ran into a bump in the road. My iTunes 12.x library contains over 20 GB of music, while my newly imported iTunes 2.x library contained only just a little over 11 GB of music! Clearly, a lot of music had been missed in the import. What was going on?

After a bit of poking around and scratching my head, I figured it out. iTunes 2.0.4 doesn’t seem to understand .m4a (AAC format) files, and would only import my .mp3 formatted (MP3 format) files. Regrettably, almost half of my iTunes 12.x library is in .m4a format and those files were not imported. Sheesh!

That vectored me off onto a bit of a side stream, as I searched for a good bulk .m4a to .mp3 converter. I did find several good converters and used them to successfully convert a few albums, but it was accomplished an album at a time, and with nearly 9 GB of albums to convert, it was simply not practical to process all the music that iTunes had not imported. For the purposes of this post, I accepted that only my .mp3 files were going to be imported, and carried on. In another post at a later time, I will go through the process of converting .m4a files to .mp3 files, so as to enable folks to pick up the REST of their music, should they head down the same road and encounter the same problem.

So, that was the first objective of the exercise completed. My iTunes 12.x music library had been imported from iTunes to iTunes 2.0.4.

Moving iTunes 12.x Library

As a side note, the process used above works very well with later versions of iTunes as well. I routinely use it to transfer my current iTunes library onto my Power Mac G5s running iTunes 9.2.1 (the last version of iTunes supported for PowerPC Macs). iTunes 9.2.1 is much more graceful about .m4a files, happily importing ALL the music in the library, .mp3 and .m4a alike.

Now it was time to try to load some portion of the newly created music library onto the 1st generation iPod mentioned at the beginning of this post. I started iTunes again, plugged the iPod into the G4 cube using the cable that came with the iPod (Firewire connectors at both ends: Firewire into the iPod and Firewire into the G4 Cube) and crossed my fingers, hoping for the best. For 30 nerve-racking seconds, NOTHING happened at all. Oh dear, I thought. Either something isn’t working, or Wikipedia has it all wrong and my 1st generation iPod isn’t really compatible with iTunes 2.0.4 after all.

Then my patience was rewarded. iTunes popped up a dialog telling me that the iPod was linked to another music library and asking if I would like to link it to the current library instead.

iPod Library Linked Dialog

I replied in the affirmative, but after a moment “thought” it came back and said that iit could not accommodate me – there was not enough room on the iPod to contain the entire library.

That was obvious of course. It was an 11 GB library and only a 10 GB iPod. I pressed the iPod icon on the lower right of the screen, bringing up the iPod Preferences window, and tried to select the “Automatically Update Selected Playlists Only”, but that selection was grayed out. Of course, that was obvious as well – I had not yet defined any playlists, so there were none to select from!

iPod Preferences 1

I resolved that problem quickly, going to “File->New Playlist” and creating a blank playlist. I then used drag and drop from the main music pane of iTunes to add roughly 8 GB of music to the new playlist. Now when I brought up the iPod Preferences, the “Automatically Update Selected Playlists Only” was no longer grayed out, and I used it to select the new playlist that I had just created.

iPod Preferences 2

Once again crossing my fingers and toes and hoping for the best, I told iTunes to sync the iPod, and off it went… or did it? To all external appearances, the G4 Cube froze. Nothing responded, not iTunes, not Finder, not anything. There was zero external feedback of any sort. Being long schooled in the ways of computers, I had the patience to wait this one out for a while, to see if it would come back. I was comforted by looking at the iPod itself, which was clearly displaying its little “syncing” icon, which was slowly and gracefully spinning around. Reasoning that if the iPod was getting what it needed, then the Mac must be supplying it, I settled in for a long wait.

About 3 minutes later, the Mac finally sprang back to life and iTunes started to copy music to the iPod. What it was doing for those VERY quiet 3 minutes, who knows, but it finally got over it and started to do what I had asked it to do. Whatever it was up to, keep in mind that this was 3 minutes with a 1.2 GHz G4 doing the heavy lifting. If you are using a slower machine, or perhaps less than the 1.5 GB complement of RAM in my G4 Cube, you may need to wait for a considerably longer period. Perhaps a coffee break would be in order!

About 15 minutes later it was done, and playlist had been loaded onto the iPod. These may be older, slower machines, but Firewire is still pretty fast – it is just a little bit faster than USB 2.0 – and so the transfer of 8 GB of music really did not take THAT long.

Firewire Logo

I ejected the iPod via the Eject control on the lower right of the iTunes window and disconnected the cable. A quick check of the music on the iPod showed that it had been successfully loaded, and all seemed well. I plugged in a set of earbuds, selected a song and was greeted with glorious sound. All really WAS well!

And so gentle readers, you CAN fairly easily transfer a modern iTunes library to iTunes 2.0.4 / Mac OS 9.2.2 (albeit without any of its .m4a content), and you CAN equally easily use iTunes 2.0.4 to load up to 8 GB or so of that music onto a 1st generation 10 GB iPod and enjoy the results. Consequently, the Christmas music here at the Happy Macs Lab will henceforth be provided by said 1st generation iPod, proving once again that older technology is still very useful technology, and is more than capable of bringing to your life today the same joy that it did when it was first new. Enjoy!

One thought on “Move Current iTunes Library to Mac OS 9 / iTunes 2.x and 1st Generation iPod

  1. Thanks again for your article. It seems I am going down the same path as you lately, as I keep stumbling across very helpful posts you have made. I recently subscribed to iTunes Match so I could download all of my iTunes Store purchases in non-protected format (since I have been a user a long time, many of my purchases were in the older iTunes Protected format). I ran into the same issue that you did — I couldn’t find an OS 9 media player that could handle the m4a files. I am currently using iTunes 12 to convert all the M4A files into 256-kbps MP3 files. I did some experimenting to see if I could get away with a VBR file or 192 kbps, but with nice headphones, I could tell a difference on some complex music and decided to just go with 256-kbps MP3s. The MP3 files are actually smaller, on average, than the MP4 files from the iTunes Match service. Thanks again for your helpful post!

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