Often, I'm listening to music on my iPod, and want to copy a file onto it. As soon as I plug it into the computer, it stops playing music. How can I prevent it from stopping?
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iPod Prevent iPod from stopping when plugged in
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You can resume? Whenever I unplug it again, it returns to the main menu and I need to find the song again.
I know on the Windows version of iTunes, you can hold Ctrl+Shift while plugging the iPod in to disable autoupdate. I've never tried it on the Mac version, but I'd assume it's Command+Shift, or somesuch. That might keep it playing, but I don't know.
Doesn't work. My problem is not with iTunes loading (it doesn't), but just with the iPod stopping as soon as it is mounted. By the way, I'm using Windows. If I was on my Mac I'd be using iTunes instead of my iPod 
Yeah, basically you cant.
You cant connect your iPod to your PC and continue listening to the song on it while you are updating the music. PC or Mac. Doesnt matter.
What you can do is connect it to your PC, play a song, and then update.
This is really all there is to it.
Another problem with the iPod right now is the Okay to disconnect screen. For my 3rd gen, I cant have it docked and unmounted to charge and play music through headphones cause of this. I think its been updated in the newer ones though. Not sure.
You cant connect your iPod to your PC and continue listening to the song on it while you are updating the music. PC or Mac. Doesnt matter.
What you can do is connect it to your PC, play a song, and then update.
This is really all there is to it.
Another problem with the iPod right now is the Okay to disconnect screen. For my 3rd gen, I cant have it docked and unmounted to charge and play music through headphones cause of this. I think its been updated in the newer ones though. Not sure.