Strange iTunes behaviour when configured to automatically sync music to iPod

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In one of my recent posts I thought I had stumbled upon a great way to synchronize all of my podcasts to my iPod and still be able to use smart playlists to listen to them on the iPod.

However, it turns out that when you have your iPod configured to automatically sync with your iTunes library it is not possible to play that music/podcast/whatever from within iTunes. You can play the content without any problems using the iPod directly, but with it connected via iTunes all of the tracks are greyed out and you can’t click on the play button in iTunes (even on the computer you are sync’ing with). This is particularly annoying for me because I have all my music at home and I want to listen to the music on the iPod at work through iTunes.

As of yet there is no iTunes store purchased content on the iPod since the New Zealand store just opened days ago, hoorah! So, it seems pretty weird that I can’t play any of the content via iTunes. Initially I thought that it was because I hadn’t authorized my work computer since I’d just opened an Apple account. It wasn’t though - authorization didn’t do anything. Reading the iTunes help it even mentions:

"To use your iPod with more than one computer, set up iTunes to manage songs manually."

Oh well. The workaround at the moment is to switch between manual synchronization turned on at work, and automatic synchronization at home. A little bit painful but seems to work as needed.

The best way to manage podcasts on an iPod

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While updating my iPod this evening I ran into a better way to manage podcasts. It’s so simple I don’t know why I didn’t do this when I first started using the podcast smart playlist hack to get podcasts to play nicely on the iPod.

The original smart playlist hack was done because there are a couple of problems with standard podcast synchronisation and playing behaviour on an iPod.

First, as soon as you start listening to a podcast (or anything I believe) it is marked as played. So, synchronizing non-played podcasts doesn’t work very well because I often loose what I was part way through listening. To combat this I have previously configured my iPod Nano to synchronise only checked podcasts so I can actively remove podcasts that I have actually finished listening to off the iPod.

Second, the standard behaviour of listening to podcasts on the iPod is bizarre. It plays one podcast and then as soon as it is finished jumps back to the list of the podcasts in the feed. Pretty hopeless since I listen to the podcasts in the car on the way to work and many of the podcasts are only a few minutes long. To address this I have additionally had appropriate smart playlists configured on the iPod so that I can listen to each podcast one after the other based on feed. Playlists work as expected, carrying onto the next item once the current one finishes. The smart playlists are easy to setup using Podcast is true and then matching appropriately on Artist or Album.

With my latest configuration I don’t synchronise podcasts to the iPod Nano at all. I simply synchronise the podcast related smart playlists. I still have the music synchronisation configured to only pull across checked items so I can remove podcasts that I have listened to and prevent music that I don’t really want to on the iPod. So simple.

Everything is much easier to manage now with the rest of the space on the iPod is filled up with a number limited randomly ordered music smart playlist. Excellent.

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