Well, I guess I can now consider myself to be in the ranks of the 'trendy'... I’ve finally got one of those sexy little music boxes (complete with white ear-buds) to call my own. Yes, that’s right, I’m now a proud owner of my very own iPod. My girlfriend got me the 1GB iPod Shuffle for my b-day, how sweet is that!

I’ve been playing with her 4GB Mini since Santa brought it to her for Christmas and I love it. So, when I started playing around with my new Shuffle I just assumed it would work just like the Mini and big-boy 'Pods do (at least as far as transferring songs to/from the iPod goes). I was wa-rong!

Here’s how it went

1. Plugged my new Shuffle into my PC (WinXP, iTunes 4.7.1, Winamp 5.08 Pro, ml_iPod 1.13). Windows recognized the device and assigned it a drive letter (at least for a few seconds).

2. Opened iTunes and was prompted to setup my new iPod. This basically consisted of giving it a name and registering it. Done! iTunes then finished 'Updating' the Shuffle and it appeared as one of my 'Sources'.

Note - I personally hate iTunes... particularly because it won’t let you manage your music library the way you want to. I have my own system of organizing my music by <genre><artist - title>. However, iTunes doesn’t like to put the artist in the file name, and insists on using the Album name in the directory structure. For this and MANY other reasons, I prefer Winamp for organizing and listening to my music collection.

3. Now, since I dislike iTunes, I fired up Winamp to move some sons onto the new 'Pod (as I’ve done many times with my girlfriend’s Mini). As I expected, the Shuffle showed up in Winamp’s Media Library under the Devices section. I then right-clicked and entered the iPod Configuration menu and took a look to make sure my preferences were OK, and they were.

4. Next I clicked on my the Audio link under Local Media to find some songs to transfer the iPod. I did a quick search to filter down the list and then selected a few songs. Then a right-click -> Send To -> iPod and the songs are transferred over... or did they? I noticed that Winamp’s Media Library said the Shuffle had 21 songs, but it had only used up around 12MB of storage...?

5. Shut down Winamp and fire up iTunes. iTunes does it’s "Updating iPod... Do Not Disconnect" thing, and when its done I click on the Steve’s iPod link (like in step 1) and bam! No Songs, WTF!?! Then at the bottom I make sure to uncheck the Replace All Songs when Autofilling option (this way it will only fill to capacity and not delete songs off the iPod).

6. Shut down iTunes and fire Winamp back up and tried steps 3-4 again... same thing. Winamp says I’m putting songs on, but only about 1/6 are actually going on the iPod. Time to do some Googling and find a few answers:

• In iTunes, go into your iPod config options and Enable disk use. This will tell the iPodService to allow Windows to keep the assigned drive letter to the drive (so you can access the files and folders from Windows Explorer).
• The reason only some songs were being put on the iPod is ml_ipod (the Winamp plugin that allows you to manage your iPod from w/in Winamp) tries to fill the Shuffle like any other iPod - by filling the folders in <iPodDrive>iPod_Control\Music\ named F00-F19. However the Shuffle only comes with folders F00-F02. It would appear these directories are used as hashbuckets to store the actual music files (but this is only my guess). Anyhow, iTunes knows the difference between a Shuffle and the bigger iPods, so it only uses F00-F02 when filling the Shuffle. However, ml_ipod is not aware of the difference (at the time of this writing anyhow) and so when it tries to fill a bucket that’s not there, it just skips that file. One fix that will allow you to use ml_ipod is to just create the missing directories yourself, or use ml_ipod to format your shuffle. You can do this by opening your Winamp Preferences -> General Preferences -> iPod Support and clicking the Format iPod button.
• At this time there still is no work-around to prevent iTunes from deleting (or auto-syncing/auto-filling) any files on your Shuffle (not put there by THAT instance of iTunes) when you connect it to your machine and open iTunes. Unlike with the regular iPods, you can’t choose to 'Manually Manage' your songs. You also can’t edit any of the files on your Shuffle after using iTunes to load it up (including syncing playcounts and ratings between anything-other-than-iTunes and your Shuffle).
• Finally, the Shuffle & iTunes will NOT let you hook up to any more than one (1) iTunes Library at any time. For example, you use iTunes at home to put some tunes on your Shuffle. Go to work. Hook up your Shuffle to your work PC and open iTunes - iTunes will say that the iPod can only be linked to one (1) Library at a time, do you want to break the link and make a new one? Clicking YES = Deleting all songs on your Shuffle. NO = iPod doesn’t show up in iTunes.

And all of this means...

You have to use Winamp/ml_ipod to completely manage your Shuffle, or you’re stuck with iPukes (er, iTunes). I’m sure that Will and the boys will get better/full support for the Shuffle into one of the next version(s) of ml_ipod.

I would suggest keeping an eye on the ml_ipod forums for updates. I have decided that I will use Winamp exclusively (duh) to manage my Shuffle, and I hope you do the same!

Hope This Helps!^TM