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Recently a new version (9.0) of iTunes came out and among the changes were changes to how syncing is performed with your iPod or iPhone. Initially it broke a lot of the things I had set up to manage my Manager Tools and other podcasts. I want to share what I've figured out so far, including a conversation with Apple Tech Support.

To start, I want to direct you to a post I made earlier introducing Smart Playlists to help you organize your growing library of music and podcasts: http://www.manager-tools.com/forums-4154

In iTunes 8, you would have to sync your Smart Playlists from the Music tab of your device. In iTunes 9.0, they have updated it so the Music tab is for syncing Playlists and Smart Playlists which have music in them. The Podcasts tab is where you work with individual shows, episodes, and playlists. I didn't see this at first because on my monitor I have to scroll this tab to see at the bottom the list of Include Episodes from Playlists.

In iTunes 8, I would sync the 3 most recent unplayed episodes of all my podcasts and some selected Playlists and Smart Playlists. My work with Apple Support Center and some of my own troubleshooting indicates that this is an either or situation now. The good news is that you can use Smart Playlists to approximate this behavior.

In iTunes 9.0, if you want to sync episodes from Smart Playlists, start by un-checking the box for Automatically include 1 most recent unplayed episode of all podcasts. Next scroll down and look for a section titled Include Episodes from Playlists, and check all of the Playlists and Smart Playlists you want to sync.

I recommend staying away from selecting individual episodes of podcasts on this tab because you'll spend a lot of time while your iPod or iPhone is plugged in trying to organize the sync content. We want to configure the sync rules so you can plug in and walk away. Build a regular Playlist, like iPod Audio Podcasts and sync this playlist. Then you can drag and drop individual episodes from the Podcasts area into this Playlist when your iPod isn't connected. When you return to the computer, the sync is complete, the content is what you want and you can be on your way.

To approximate having 1 or 2 of the most recent unplayed episodes of all your podcasts is to set up a Audio Podcasts - New Smart Playlist:

  • Match all of the following rules
  • Media Kind is Podcast
  • Kind contains audio
  • Play Count is 0
  • Limit to 7 hours selected by most recently added

You can vary the time limits. I also added a rule for Album doesn't contain Lit2Go because I want to listen to those episodes together in its own Smart Playlist. I also have a Audio Podcasts - Old Smart Playlist which is limited by least recently added. This way I can work through podcasts from oldest to newest or newest to oldest depending on my mood.

I'm opened a new thread where we can post some other ideas for building Smart Playlists and keep them together (http://www.manager-tools.com/forums-4297). If you have learned new tricks to using iTunes 9.0 please add comments here.

Jack
Colorado

jrumple's picture

I noticed this morning that iTunes 9.0.1 is out. I installed it and will play with it some this weekend. Usually a x.0.1 build is a patch, so if you've been having trouble with 9.0, install 9.0.1 and see if the problems still exist.

jrumple's picture

After a question from another Manager Tools member, I started looking more closely at the sort order of Smart Playlists on my iPhone (OS 3.1).

It seems that on the iPhone the playlists are not in the same sort order as they are in iTunes (9.0.1). It looks like the iPhone/iPod sorts the playlist by track number no matter how you have it sorted in iTunes.

At this time the only thing I can think of is try playing the podcast episodes from the Podcasts area of the iPod. The Smart Playlist will ensure only the right episodes are synced and the Podcasts area does allow you to play episodes back-to-back in chronological order. Hopefully that is the order you want them in.

If anyone finds a better workaround or has more information on this issue, please post a reply here. Thank you.

Jack
San Diego

marcbots's picture

Not more information from me, but a thank you for sharing. Saves me a lot of time :-)

Marc 

jrumple's picture

This morning I downloaded and installed iPhone 3.1.2, the latest patch, and still the playlists have their own sorting rules. I haven't heard anything new from the Apple forums.

One idea I had was if you limit your Smart Playlists to one or two episodes selected by least recently added then sync more frequently (daily or twice a day) then you'll have fewer of them out of order. Sure it isn't ideal, but it could get us through this mix up on the iPod.

I've only had the trouble on my iPhone. iTunes playlists still sort properly for me.

Jack
San Diego

jrumple's picture

I just upgraded to iTunes 9.0.2. The issue of Smart Playlists not sorting correctly when synced with iPhone OS 3.1 is still not working.

Most of the updates from iTunes 9.0.1 to 9.0.2 were focused on better integration with the new release of the Apple TV 3.0 upgrade.

Jack
San Diego

jrumple's picture

I've found a workaround for listening to Manager Tools in chronological order (oldest to newest). Use Smart Playlists to sync the episodes you want to the iPhone, but use the Podcasts area to play them back.

We would like to have full control over the playlist play back, like was available in iPhone 3.0 and earlier, but in the interim we can listen to episodes in the order they came out. Below are more details for getting Manager Tools and Career Tools to your iPhone and listen to them in order.

Podcast Subscription
By now everyone reading this should be subscribed to at least one of the Manager Tools or Career Tools podcast feeds. iTunes makes it so easy that most people don't go back to check their subscription settings. Take a moment to open the Podcasts library in iTunes, select your Manager Tools podcast, and then select the Settings button at the bottom of the window. In here you can adjust how frequently iTunes checks for new episodes, how many to download when new episodes are available, and how many to keep in the library. This is especially helpful if you also subscribe to a lot of video podcasts which take up much more hard disk space.

Smart Playlist
Now that you're subscribed, build a Smart Playlist to make it easier to sync the episodes to your iPhone. In iTunes, select File --> New Smart Playlist. Start with the following settings. You can adjust these to your tastes later.

  • Match all of the following rules
  • Album contains Manager Tools
  • Play Count is 0
  • Limit to 200 MB selected by least recently added

This will create a playlist containing the oldest episodes of Manager Tools that you haven't listened to yet. As you listen to episodes, those will automatically be dropped and newer unlistened to episodes will take their place. When you have 8 GB, 16 GB, or 32 GB of space on an iPhone or iPod touch, it doesn't sound like 200 MB is a lot of stuff. Build this playlist and you'll find that this is over 6 hours of your favorite podcast. By limiting the space use with a Smart Playlist, you're making room for a lot of other content on your iPod. You can make another Smart Playlist for Career Tools as well.

Sync This Playlist
Now we need to make sure the episodes selected in the playlist above will transfer to our iPhone or iPod touch. Connect your device to the computer. When iTunes recognizes it, select the device. On the Summary tab, make sure the "Automatically sync when this iPhone is connected" check box. Now move to the Podcasts tab. At the top be sure the Sync Podcasts check box is checked and the "Automatically include..." box is NOT checked. Now scroll this page down to the very bottom where you'll see a list titled Include Episodes from Playlists. Scroll through this list and find the Smart Playlist we just created and check them. Now select the Apply button and those six hours of Manager Tools will be copied to your iPhone or iPod touch.

Playback in Order
Even though we created the Playlist to specify which episodes to transfer to the iPhone or iPod touch, we're not going to use it to listen to them. This is the workaround. Even though iTunes has everything sorted in any order you selected, the iPhone or iPod touch doesn't. Select the iPod application on the device. If you don't see Podcasts at the bottom of the screen, select the More button. You'll find Podcasts in this list. Select Podcasts and scroll to find Manager Tools or Career Tools. Scroll to the top of the list and you'll see all of the episodes from the Smart Playlist in chronological order. If you have episodes from other playlists on the device as well, they will be mixed in this list by chronological order.

Older versions of the iPod software wouldn't play podcast episodes continuously. You had to start each one individually. That is where playlists and Smart Playlists earned their value. Now the podcasts area will play continuously and are sorted from oldest to newest. Unfortunately playlists no longer sort the same between the device and iTunes.

If you don't have Podcasts at the bottom of your iPod application and want it there, go to the More section again and select the Edit button. Drag the Podcasts icon over the icon you want to replace with it and release. I have mine configured with Playlists, Podcasts, iTunesU, and Videos.

Refresh the Content
Now that you have everything configured, take your iPhone or iPod touch out to listen to Mark and Mike wherever you are. When you get back to your computer, plug your iPhone or iPod touch into the computer and walk away. Yes, I said walk away. Your computer and iTunes will automatically replace the episodes you have listened to with episodes you haven't. The best way to think about this is use your computer as a charging station for your iPod. Not only will your iPod have a fresh battery charge, but you'll also have fresh new content on your iPod.

This post only describes how to use one style of Smart Playlist. It is great for all sorts of podcasts that you subscribe to and want to budget memory space on your iPod. Head over to the Smart Playlists topic to find out how to use Smart Playlists to create rotating playlists of your favorite music as well.

Jack
San Diego

jrumple's picture

 Recently I upgraded both iTunes (9.0.3) and iPhone OS (3.1.3). Now all of my issues with playlist sorting are fixed.

If you haven't upgraded, do so and this should help. In working with some other Manager Tools listeners on this issue, I was reminded that not all iPods are made the same, so your mileage my vary on this issue. The iPod shuffle has a different operating system than the iPod nano than the iPod classic than the iPod touch. If you don't have an iPod touch or iPhone, please post your experiences with iTunes 9.0.3 and any other tips for getting Manager Tools to sync and playback according to your preferences. 

Thank you,
Jack
Colorado

(Yes, my project in San Diego was temporary and I'm back in Colorado.)

jrumple's picture

http://support.apple.com/kb/TS3044

I was looking on the Apple website for keyboard shortcuts for iTunes and came across the article linked above. It has a much more elegant solution to fixing the sorting problem experienced by some users in iTunes 9.

Build the Smart Playlist the way you want it. Establish the sorting you want within iTunes. Then right-click on the Smart Playlist and select Copy to Play Order.

There are more procedures if this doesn't work.

Jack
Colorado Springs