This tutorial will teach you how to synchronize (transfer) music and videos on to an iPod using Winamp. In this tutorial, I'm using the "Winamp Modern" skin, which comes with Winamp when you download it. Feel free to use whatever skin you like, this will still work the same but it may look a little different from my screenshots.

Open up Winamp then open up the "Media Library" window. To do this, simply select the Winamp Main Window and press Alt+L.

This screenshot and the explanations below will help you to understand this "Media Library" window:

The top left box (enclosed in red lines) is where you see the list of artists. Right now, on your screen, you may not see anything there. We will be updating your music list in a moment. After an artist is selected in the top left box, the top right box displays what albums you have by those artists. The box directly below these two boxes is where all the songs (either by that artist, or on a particular album, depending on what you have selected) are listed. Lastly, the red box on the far left shows what portables you have plugged in. My iPod's name is 'tr1x,' thus it shows 'tr1x' under the "Portables" category.

By selecting your iPod under the "Portables" category, you can see what music (and other content) you currently have on there, you can delete any content or move it to the computer, see how much space you have left on the iPod, and other important information. In my screenshot, I currently have "Audio" under "Local Media" selected, showing me the music I have on my computer. In this tutorial, I'm going to synchronize my two "A Day To Remember" albums on to my iPod.

First of all, we need Winamp to display ALL of your music so we can sync it. To do this, click "Library," and then "Add Media to Library..."

Note: The "Library" button is located at the bottom left of the "Media Library" window.

After navigating to and selecting your music folder(s), all of your music should show up, as the first screenshot shows. Now, right-click any song / artist / album you want (depending on what you want to sync) and go to "Send to:" then click the name of your iPod.

As I said earlier, I am going to sync all of my music by "A Day To Remember," so in this case I'm not going to sync any indivisual songs or albums, I'm just going to click on the artist and send it all to the iPod.


After Winamp begins sending music to the device, you can look at your iPod and it will be displaying it's synchronizing screen. You can keep sending anything you want to the iPod, even it it's currently busy synchronizing something else. After you've sychronized everything, click your iPod in the left pane, then in the bottom right hand corner there's a button saying "Eject," click that button and then unplug your iPod.

Having trouble? Contact me via email: admin@tr1x.com