by , 1:45 PM EST, October 29th, 2001

[Update: This story was updated, in part with help from long-time reader (and huge TMO fan) "p."]

The Mac Observer was able to spend some time with Bob "Dr. Mac" LeVitus and his review iPod unit this weekend, and together we looked at how to get around the limitations built into the iPod to keep users from sharing MP3s between different Macs.

Apple has officially said that one can not sync up an iPod to two different Macs. Specifically, Steve Jobs told the New York Times that music loaded up on an iPod can not be transferred to another Mac from that iPod. This has been an issue of some debate among Mac users, especially with those users who own and use more than one Mac (desktop and portable, home unit and a Mac at work, home unit and a Mac at school, etc.) who have legitimate Fair Use rights in transferring their MP3 files between Macs. As with all attempts at digital copy protection, Apple's measures are easily circumvented. This was noted by Steve Jobs himself as quoted in a San José Mercury News article by Jon Fortt:

There is some confusion about whether the iPod can be used to steal music. As the iPod is configured at the moment, the answer is absolutely yes. You can load songs from one Mac onto an iPod, and then dump those songs onto another Mac -- or onto several other Macs.

Apple discourages music piracy. The company said it spent more than $50,000 on CDs to make that point at the iPod launch: Apple purchased and distributed 20 CDs to use with each iPod review unit, and iPods out of the box have a sticker reading "Do Not Steal Music."

Unlike some other technology makers and the major music labels though, Apple's position is that music piracy is a behavioral problem, and that it is futile to attempt to build encryption technology that forces people to change their behavior. People who are intent on stealing will steal.

"Every security scheme that is based on secrets eventually fails," Jobs said.

So Apple has made it a bit tricky to use the iPod to swap songs between two Macs -- but only a bit. I did it by turning off the automatic synching feature on my home machine and dragged songs onto the iPod. I then connected the iPod to someone else's iBook. That iBook already had iTunes 2 installed, and had already been linked to another iPod.

The iBook noted that this was not the usual iPod, and asked if I wanted to wipe all the songs off the iPod and start over. I said no. But the iBook recognized my iPod anyway, and let me drag songs off of the iPod and into the iBook.

In other words, by turning off the automatic sync functions and saying "no" when asked if you would like your iPod library erased, you can simply drag and drop your iPod music files from iTunes to another Mac.

While this is the case with the pre-release version of iTunes 2 and the iPod, it may be changing with the final version. After the initial announcement, the iPod FAQ was changed to say that copying from the iPod to the Mac would not be possible. A screen shot from the iPod FAQ PDF:

In a nutshell: You can load up tunes from different Macs onto your iPod, but you can not then take files from your iPod and either automatically or manually put them onto a Mac. This directly contradicts our own experiments and seems to indicate a change in the software from iTunes version 2.0f13 (the pre-release version in our test unit) is in the works for the final version. Unfortunately, we likely won't know until the final version ships.

One thing that is not likely to change is the way your iPod stores music. The iPod keeps music synced up via iTunes 2 in a hidden folder on its internal hard drive. Hidden folders or files can be used by the operating system and apps, but can't be seen by users. When a Mac user has mounted an iPod on the desktop, the MP3s are right there, but you simply can't see them in the Finder. The ones you can see aren't used by the iPod. It's a neat trick to try and limit copying, but it's one that is easily bypassed. Again, we can't be sure until the final version ships, but to get around this limitation, one simply needs to be able to see invisible files. Unless the files become encrypted, which is not likely (see Steve Jobs' comments as quoted above), this should hold true in future versions.

To see invisible files, you need software to turn on this function. Fortunately, the Mac OS X developer community has released a variety of tools that allow users to see invisible folders and files. For instance, TinkerTool has an option that allows hidden and system files to be visible at all times.

Once you have enabled this, invisible folders show up in Finder windows like your normal folders, only the icons are slightly greyed out. Once you get to your files, you can copy and move them like any other file on your Mac, including copying them from the iPod to the drive on your Mac, your second Mac, or any other Mac. The image below shows the path to find your MP3s on your iPod.

There are other utilities that make this possible with Mac OS X as well.

On the Classic Mac OS side, we tried accessing the music files on an iPod with DiskTop, a Classic Mac OS utility that was last updated in 1994. That utility will also allow you to see and manipulate hidden files, among other things. We were able to find and copy the iPod's music files from within that app in Classic very handily.

The Mac Observer's prediction is that it is only a matter of time before some clever coder releases a utility that is designed to specifically allow the music files to be seen with an iPod.

Piracy options are limited with the iPod because it requires the music stealers to have physical possession of the original iPod owner's iPod. This basically takes us back to the days of taping LPs or CDs by would-be pirates, and is a far cry from the pirate-friendly environment of Napster, Gnutella, and other file trading Internet-based services.

We would like to thank Bob LeVitus for working with us on this article.

The Mac Observer Spin: