Q: I am considering getting an iPod but I have a question about the song pause feature. How does it work? Can you turn it off and pick up where you left off without having to fiddle with it?

– Bob
A: Normally if you pause a song and leave the iPod alone, it will retain its place in that particular song. There are two exceptions to this, however:
Firstly, iPod models prior to the fifth-generation iPod and iPod nano had a “Deep Sleep” mode that the iPod would revert to after 36 hours of not being used. When going into “Deep Sleep” mode, the “Now Playing” list would be cleared, as would the playback position of the current track. This is no longer an issue with current generation iPods, however, so you don’t need to worry about this unless you’re considering purchasing an older model used iPod.
The second issue is that the “Now Playing” list is cleared whenever you connect your iPod to a computer, whether to sync it or use it as an external hard drive. This happens even on current model iPods, and the playback position of the current track will also be lost in this case as well. However, unless you’re regularly connecting your iPod to a computer, this should not be a concern either. Note as well that connecting the iPod to non-synchronizing accessories such as power adapters and portable speakers does not affect this.
If you want to retain the iPod’s current playback position for specific tracks, there is another option, however. You can set individual tracks in iTunes to “Remember Playback Position.”
This will tell iTunes and the iPod to keep track of your position in a current track, regardless of whether you stop the track, select a new track, or synchronize it to your computer. As an added bonus, in automatic sync mode the playback position is even transferred from your iPod to your iTunes library during the next sync, so you could pick up where you left off when you return to your computer. This feature is intended primarily for audiobooks, but can technically be used on any track by setting the appropriate option, and you can even batch-set this option on multiple tracks in iTunes.