Q: For any given week, I like to put my favorite tracks in an On-The-Go playlist on the iPod, but when I plug in my iPod to my computer at the end of the day it turns my On-The-Go into a permanent playlist. I really don’t want this to happen, so I can continue modifying the same playlist, taking off and adding on songs as I like. Is there a way to keep my dynamic playlist dynamic?
A: The transfer of an On-The-Go playlist to iTunes (thus making it static) upon every sync is a built-in feature of iTunes that can’t be disabled. However, you can continue editing and adding to this track listing on your iPod after a sync by simply creating a new On-The-Go playlist based upon the most recent static copy that iTunes created.
After you disconnect your iPod, simply browse to “Music → Playlists”, highlight the playlist that iTunes created from your OTG playlist, and hold down the center button, creating a new editable copy.
Granted, this will create a new static playlist in iTunes each time you connect to your computer, but if you continually delete the oldest one, you can continue editing your playlist while away from your computer in this manner.