First off, I get why Apple makes it difficult for people to get music off their iPod and onto a computer. They pretty much have to, or the RIAA would never work with them. DRM is one thing, but if people were buying CDs, ripping 60GB of music onto an iPod and then giving that iPod to a friend, that's a whole lot of illegal copying in one fell swoop. I'm not sure why Apple hasn't made it possible to transfer music from an iPod onto the system with which that iPod is registered, but it's not like it really matters. Senuti is here to do that for you.
There are actually many applications available for copying music from an iPod to a computer, but I prefer Senuti for two reasons: 1.) You can take whatever songs you want and put them wherever you want, and 2.) It's free.
I went searching for an application like this when I bought my iPod classic to replace my 5G iPod. There was a lot of music on the 5G that I only had on the iPod or on CD, and because I create most of my playlists directly on the iPod through iTunes, I would've had to recreate everything on the classic. I also didn't want to have to rate all of my music again, but unfortunately, that didn't work out here. More on that later. For now, using Senuti.
After downloading the program and launching it, Senuti will first ask where you want to place your music. They recommend your iTunes music folder, but I disagree. I find it's just easier to manage if you put your music somewhere else, first. Putting it in a folder on your desktop can serve to remind you to back it up to another disc or CD. That's also better if you're pulling music from your iPod specifically to back it up. Also, despite Senuti's best efforts, it's still fairly simple to accidentally double up music on your computer or have songs hide in the wrong folder.

On the other hand, if you're not pulling off too many songs, putting it directly into your iTunes music folder does make sense. So, set it up for how you plan to use it, but know you can change your default setting at any time in the preferences panel. No matter which method you choose, as mentioned above, Senuti will help you know what needs to be pulled. Songs already in iTunes on your computer will have a blue dot next to them so you won't accidentally double up your tracks. This even works if you're dragging and dropping a playlist from your iPod to iTunes. Songs in the playlist will not be copied down from the iPod if they're already in iTunes, but they will be pulled from iTunes to the playlist. Understand, though, that some songs may not end up in the correct place if they're not labeled properly. For instance, in the image below, note that four songs off Puffy's new album Honeycreeper don't have the blue dot. This is because I slightly altered the name on my iPod. In the case of "Closet Full of Love," all I did was make the "o" in "of" lower case. This was enough to confuse Senuti, however, so you can't always trust it.

The Senuti preferences allow you determine if you want a loose or exact comparison when avoiding doubles. I selected loose, and still had this capitalization issue. It's not a major problem, just something to consider.
Going back to set-up, Senuti will also tell you to make sure that disk use is enabled on your iPod. Along with quickly telling you how to do this, they offer links to both their site and Apple's for further instructions and information.
Once you're in Senuti and your iPod is connected, you'll see a window that lists your iPod and playlists on the left had side, along with your iTunes playlists directly below that. Selecting any of these will show the associated songs in the main area on the right. Select Library under your iPod, for instance, and you'll be able to scroll through all of the songs on your iPod.

If I wanted to copy everything to my computer, I could just click on Library and either choose "Select All" from the Edit menu or click on any song in the library window and hit Command+A on the keyboard. It's then just a matter of clicking on the green transfer arrow on the upper left of the window, and the songs will begin to download to the specified location. When the tracks download, they do so in the same manner in which they're organized on your iPod; songs will appear in a folder named after the album on which they appear, and albums are placed in a folder under the band name. Everything stays nice and neat.
Whether you're taking an entire iPod's worth of music, just a few albums, or maybe even just a playlist, all you need to do then is drag the music back to your iTunes account. Done. It really is that simple. However, there are a couple of things to consider.
First, if you download DRM protected music, you will only be able to play it on the computer/iPod with the iTunes account to which the song is registeredSenuti does not remove any copyright protection. That shouldn't be a problem, though, as you're only doing this to back up your legally purchased music, right?
RIGHT?!
Second, although Senuti does give you the option to determine what meta data is copied down with the file, I found that it didn't remember everything I told it to. Some album artwork was lost, and none of my song rankings made the transfer when though I made sure the option was checked in the Senuti preferences. That's annoying, but not a deal killer, as I would have to re-rank my music if I were ripping it from CD again, anyway.

By following this simple process, I was able to copy 11GB of music from my 5G iPod to my iPod classic without missing a beat. No re-ripping of CDs. No hunting through multiple DVD back-ups, and, most importantly, no repurchasing of songs bought through the iTunes store for music I forgot to back-up or lost in my accidental hard drive wipe-out last year. Anyone upgrading an iPod should download and use this program. It's free, after all. It's also worthwhile if you have a lot of music on your iPod that you've never backed up.
I opened this article with the suggestion that the capabilities provided by Senuti should be built into the iPod. I stand by this. But as long as programs such as Senuti are available to usfor free, evenI'll forgive Apple's willingness to place nicely with the music industry. Senuti is easy to use, offers a host of nice features, and makes you feel a bit rebellious while you're using it.
And isn't that what rock music is all about?
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Ooh, thanks for the Winamp plug-in tip for iPhone->Windows, y’all. Updating the post now.
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