Cannot sync ‘Now Playing’ queue between iPod and iTunes

Q: I would like to be able to hear the same music (“Now Playing”) at home and on the road. The songs and playlists on my fourth-generation iPod touch are exactly the same as the ones in iTunes 10.5 on my Windows 7 laptop. What I want is to be able to seamlessly be able to have the music on my laptop pick up where I left off on my iPod when I walked in the door and the Wi-Fi kicked in. I also want to be able to do the reverse… have my iPod pick up playing where I was in iTunes. I have WIFI 2 HIFI, which is a neat program, but it really doesn’t do what I want to be able to do.

Any ideas? Recommendations?

– Robert

A: Unfortunately, this isn’t really possible even with a third-party app due to the way that iTunes and iPod synchronization works.

Firstly, your “Now Playing” queue is only stored on the device you’re currently listening to—it does not get synchronized to other devices or your iTunes library. Further, your current track’s playback position is not normally synchronized back to iTunes unless you’ve specifically enabled the Remember Playback Position option for that particular track. However, this option is persistent and really intended for media such as audiobooks and podcasts; the playback position will be remembered even if you partially listened to a track several months ago, making it a generally undesirable option for music listening.

While one could theoretically kludge something together based the Remember Playback Position setting and the last played times in the iTunes library, this would not be an elegant solution and would definitely not be seamless—you would basically have to wait for your iPod touch to finish syncing with your iTunes library before playback could be resumed from iTunes.

A more effective solution is to simply take iTunes out of the equation and stream music playback directly from your iPod touch wirelessly to your home speakers using either AirPlay or Bluetooth technology. In many cases this wouldn’t automatically start playback on your home stereo as soon as you walk in the door, although some Bluetooth speakers and audio accessories are capable of automatically picking up playback as soon as the iPod touch comes within range. Even so, however the AirPlay and Bluetooth streaming controls are easily accessed from the lock screen of your iPod touch, requiring only two or three taps to switch over to an external audio source manually.

A wide range of standalone AirPlay and Bluetooth speaker systems are available, but if you already have an existing home stereo system that you want to use you can also easily pick up a device such as Apple’s Airport Express or Apple TV for AirPlay or any one of several third-party Bluetooth adapters for Bluetooth streaming.

In most cases you’ll find that AirPlay is the more appropriate option for a whole-home audio solution as it uses your existing Wi-Fi network and is not constrained by the more limited point-to-point range of Bluetooth devices.