As I understand it, yes. The reason is that it's been designed so that this exact thing does not work (easily, as you seem to think it should).

I am assuming that your buddy has already hooked his ipod to his computer, and downloaded some music to it, and now he wants some of yours, too, right? If so, then, as I understand it, his ipod knows that it 'belongs' to another computer, and wants nothing to do with yours, at least as far as being an ipod. It may be that it'll be a usb drive though. (some of that was extrapolation of my knowledge base, so if someone else can expand or correct this, that'd be cool)

[speculation] Do a little searching on the web. It is likely that what you are trying to do (transfer downloaded nusic from one computer to another via an ipod) is possible, but it probably takes a lot more effort than you think it should. [/speculation]

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"You'll find a slight squeeze on the hooter an excellent safety precaution, Miss Scrumptious."

"I can live with doubt and uncertainty and not knowing. I think it is much more interesting to live not knowing than to have answers that might be wrong." -- Richard Feynman

I saw this in the Wall Street Journal last week. I will assume you don't have access so I will copy it here for you. Let me know if you have success.

[/url]

January 12, 2006 PERSONAL TECHNOLOGY By WALTER S. MOSSBERG


Software to Help You
Download From iPods,
Share iTunes on 1 PC
January 12, 2006; Page B1

This week, Apple Computer announced that it sold a staggering 14 million iPod music players over the recently ended holiday quarter -- more than 100 every minute. But as popular and well-designed as the iPod is, it's not perfect. There are a couple of aspects of the way it works, or doesn't work, that are becoming increasingly annoying as people acquire both more iPods and more computers.

First, you cannot use an iPod, out of the box, to copy your music collection to multiple computers you may own. Millions of iPod owners have more than one computer, and it's perfectly legal to copy the music you own to more than one computer. But the iPod won't help you do this.

Second, in families with multiple iPods sharing a single computer, the iPod's companion software, iTunes, doesn't allow you to have multiple music libraries. With multiple libraries, each user could see only his or her own music, and could synchronize his or her iPod with that personal music library.
Apple is aware of these shortcomings, and I wouldn't be surprised to see it solve the second one, multiple libraries, this year. But the first, the inability to use the iPod to copy music to multiple computers, is tougher. Apple was forced to cripple the iPod in this manner at the insistence of the record labels, which feared that it might be used to copy music too widely. So a fix probably requires negotiations with the labels, whose obsession with piracy has caused them to treat their own customers like criminals.

Luckily, there are solutions to both problems available today, through third-party software or workarounds. Here's a guide to those solutions.

First, here's how to use an iPod to copy music to multiple computers. You just have to download and install one of a number of small utility programs designed specifically to let you copy the music on the iPod to a computer. There are lots of these, for both Windows and Macintosh computers.

For Windows users, I suggest CopyPod, available for $20 with a two-week free trial, at www.copypod.net2. For Mac users, I like PodWorks, available for $8 with a limited-function 30-day free trial at www.scifihifi.com/podworks3. Another, similar program, which comes in versions for both Windows and Mac, is PodUtil, available for £10 ($17.66), with an unlimited free trial, at www.kennettnet.co.uk4.

Once you have installed one of these utilities on your second computer, just plug in your iPod, filled with the music from the first computer. When iTunes pops up, be sure to decline when the program asks if you want to synchronize your iPod to the second computer. If you don't decline, iTunes will wipe out your iPod's contents and replace it with any music on the second computer.

Next, quit iTunes and launch the music-copying utility, if it didn't launch automatically when you plugged in your iPod. It will scan your iPod, displaying all the music stored there, and allow you to copy some or all of the music onto the second computer. If you have a lot of music on the iPod, this could take awhile.

When you're done, just quit the utility program, disconnect the iPod, and relaunch iTunes. In some cases, the utility will already have populated iTunes with the copied music. In other cases, you'll have to use the "Add to Library" command in the iTunes File menu to bring in the music you have just copied.

How about the multiple-libraries problem? This one can be solved with some workarounds, as well as third-party software.

Suppose you want to synchronize only part of a library to a particular iPod, say mom's iPod, in a family with several iPods. You can place the songs mom wants into a playlist called, for instance, "Mom's iPod Songs." Then, when mom's iPod is connected, you can go into the Preferences settings in iTunes to designate that mom's iPod will automatically be synchronized only with the songs in that playlist, rather than all the songs in the library.

Or, you can go into Preferences to designate that mom's iPod won't be automatically filled at all, but will be filled manually. Then, you could manually drag all the songs she likes onto the icon representing her iPod within iTunes.

A better approach is to download a utility program called Libra, which comes in versions for both Windows and Mac. Libra, which costs $10 with an unlimited free trial period, is available at homepage.mac.com/sroy/libra5. It allows you to create multiple libraries, and to switch among them.

You just run Libra, create a library -- for instance, Mom's Library -- and then select it. Next, you launch iTunes, and it comes up with only that library displayed. The first time you set up a new library, it will be empty. But you can just use the iTunes "Add to Library" command to fill it up with songs from your hard disk. You can then set up playlists that will be displayed only in that library. And you can synchronize the whole library to an iPod of your choice.

Multiple libraries can use the same songs without the need to store multiple copies of the songs.

Let's hope Apple can build these features into the iPod and iTunes soon. Until then, the utility programs are your best bet. • Email me at mossberg@wsj.com6.

Thanks for your input. I finally got it to work. I restarted evertything again and switched USB ports and it worked. My buddy lost all 16 songs he put on it but picked up 2500. Thanks again for your time.

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Doug in Michigan

Apple is very careful about how you can share music. For instance, you are only allowed to authorize your iTunes account to a limited number of computers. I learned this when I dropped my laptop and killed my hard-drive. You might try getting on your buddies computer and getting into iTunes and authorizing his computer to access your iTunes account, then trying to sync from there. No guarantees, but it might work. Otherwise, there are all kinds of software patches on the web. You'll probably find something to help you out if you look hard enough.

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Slowguy

(insert pithy phrase here...)

This guys article fails to recommend a util called SharePod. Basically, it sits on your iPod and allows you to pull music off of your iPod on to ANY PC - as long as you have it setup as a data drive. Real easy to do and lets you pull music off of your iPod and give it to anyone. i have it on both my iPod 20GB and my nano and it works like a charm.