I recently posted about a trick in iTunes to fix an issue where the sort order chosen for a playlist in iTunes doesn’t get copied over to the iPod unless you right click on the playlist in iTunes and choose “Copy to Sort Order” before syncing.

In a strange twist of fate this trick stopped working for the Smart Playlist I use to listen to Podcasts on my iPod Touch within days of posting the tutorial. It seems that a new bug appeared in either the iPod OS 3.1.x, or perhaps in iTunes itself, and so far there is no official fix.

The issue is that certain combinations of settings for Smart Playlists result in the sort order selected in iTunes not being synced onto the iPod, regardless of whether “Copy to Sort Order” is selected. Note that the sort order appears to transfer if you look at the iPod version of the playlist within iTunes, but not when you look on the iPod itself.

There are various combinations of settings for the Smart Playlist that will resolve this problem (including turning off “Live Updating”, but that defeats the purpose of using a Smart Playlist for Podcasts in the first place), and certainly multiple combinations for which the error occurs. I haven’t even begun to look for all of them, but I have found one that works very well and gets my Podcast Playlist working perfectly.

If you want iTunes to be able to update your Smart Playlist for Podcasts correctly with the sort order you selected in iTunes, try setting up your playlist as follows:

1. Checked: Match ALL of the following rules:
2. Playlist IS NOT Music
3. Media Kind IS Podcast
4. Checked: Match only checked items
5. Checked: Live updating

Most likely the only change is the addition of item 2 above. The other settings are all defaults for Smart Playlists and will only be different if you intentionally changed them for some reason.

NOTE – You will still have to use the “Copy to Sort Order” trick I previously posted (because that’s how iTunes was designed). Today’s fix merely gets you back to the point where that trick actually works…

I have submitted this as a bug to Apple, but similar bugs have existed for ages so I’m not holding my breath that they’re going to fix this one anytime soon.

I listen to lots of Podcasts on my iPod Touch and I prefer to listen to them in the order that they are released. Podcasts are much like radio or TV shows in that the information presented is often timely, or at least referential to prior episodes, and so it generally makes more sense to listen to shows in the order they are released so that related and timely information is heard around about the same time.

The included “Podcasts” view in iTunes and on my iPod Touch groups different episodes of the same show together with no option to see all episodes of all shows in one big list. This makes it easy to listen to all the episodes of one show in the order they were released, but virtually impossible to listen to all episodes of all shows in the order they were released.

I got around that by creating a Smart Playlist that searches my iTunes Library for Podcasts. My preferred sort order for that playlist, naturally, is by date. That sort order gets transferred over to the iPod initially, and as new shows are added (as they automatically get downloaded by iTunes) they get added to the end of the list in the order they are downloaded. This works extremely well for me most of the time.

Unfortunately every once in awhile the sort order on my iPod gets out of whack (seemingly at random, and in a totally random order), and there is no way on the iPod to reorganize playlists. /They can be reorganized in many different ways in iTunes (by artist, by date, alphabetically, etc.), but I couldn’t figure out how to sync those changes back to my iPod. No matter what I changed in iTunes, the sort order on my iPod stayed scrambled.

Finally I noticed a cryptic command on the right-click menu for the playlist called “Copy to Play Order“. I still have no idea what the name of this command is supposed to mean, because it doesn’t do anything to the playlist in iTunes, but after choosing this option and syncing the iPod to iTunes, the sort order for my playlist magically matches with that in iTunes. Yay!

I don’t understand why I would have to take this extra step as it seems obvious to me that if I can’t sort my playlists directly on the iPod, but I can in iTunes, then I probably want the sort order on my iPod to match what I choose in iTunes. Is that so much of a stretch??

In an interesting twist that I haven’t seen mentioned anywhere else, the free Skype App for the iPhone is now available to Canadian users of the iPhone and iPod Touch. For reasons that nobody could adequately explain to me, the app was initially only available for US based users. I was therefore very surprised when I came across it in the app store on iTunes yesterday. I wonder if this has anything to do with the recent purchase of Skype by a conglomerate that includes the Canada Pension Plan Investment Board??

Skype is a very cool app that allows iPhone and iPod users to make voice calls over the internet, using either the 3G network (iPhone only) or a WiFi connection. Calls are free to other Skype users and inexpensive to landlines and mobile phones. The Skype service also includes additional features such as instant messaging, file transfer and video conferencing; however, only some of these features are currently available with the app.

This is very exciting because the iPod Touch can now be used as a phone (if you have an add-on microphone) anywhere that a wireless internet connection is available. For many users that will be all day long in their home and office locations, or even at McDonalds and Starbucks locations that off WiFi service to their customers.

How long will it be before WiFi is available everywhere? That would eliminate the need to carry a mobile phone and/or to pay for an expensive data plan.

I love my iPod Touch and I use it all the time. Before I actually got one I had been coveting it for a long time.

Without doing all that much research on it I naturally assumed that it would consist of the exact same hardware as the iPhone, and would be missing only the ability to make and receive phone calls. I was quite surprised to discover that the hardware was actually quite different; the Touch was smaller and lighter, and, most significantly, did not have a built-in camera.

Fast forward about 18 months to the launch of the iPhone 3Gs which included not only an improved still camera, but also video camera functionality. It also received a wide variety of software upgrades in the form of the iPhone OS 3.0. At that time there was no corresponding launch of new hardware for the iPod Touch, but the existing device got a de-facto upgrade since it was compatible with the OS 3.0 upgrade. Everyone naturally assumed that Apple was simply stalling in order to ensure high demand for the upgraded phone, and that new hardware for the Touch would follow a few weeks of months later.

This finally happened this week when Apple released a whole new lineup of iPods.  This release also came with a major update to iTunes 9.0 and also to the iPhone OS 3.1.  Some of the highlights of the release include:

• new colors and lower prices for the iPod Shuffle
• a massive 160 GB hard drive in the iPod Classic
• a faster processer in the iPod Touch (the same as in the iPhone 3Gs) and a new 64 GB model
• a video camera (with microphone and built-in speaker) and FM tuner in the iPod Nano

What?  The Nano gets a video camera, but the Touch doesn’t? 

Video is king right now and I can see why apple would want to shove a camera into all of their iPods.  But never in a million years did I expect to see it in the Nano before it was in the Touch.  The iPhone already has it so it seemed like a lock that the Touch would get it next.  My 32GB 2nd gen iPod Touch is plenty fast enough and without a camera in the new generation I’m really not sure why any existing iPod Touch owner would upgrade to the new model.  Even new iPod buyers should be able to pick up some great deals on the 2nd Generation devices.  For me this announcement is just plain odd.

Oh well, maybe bext time.

Up until now I’ve been using Goosync to manage my Calendar on my iPod Touch.  It wasn’t perfect, but it was the only way I could find to sync my iPod with my Google Calendar, which I use for everything.  In fact I just recently wrote about using GooSync as one of my favorite iPod Apps.

Well that all changed today when I downloaded the iPhone OS 3.0 Software Update.  Sadly this is a free update for the iPhone, but it costs $10 for the iPod Touch.  I looked carefully at the updated features (there are over 100) and decided that it had enough for me to justify the outlay.  The best update as far as I’m concerned is to enable direct syncing with external calendar services using CalDAV or iCal.  Although Google really hasn’t made it easy to figure out how to do it, they released support for CalDAV almost a year ago.  They have some detailed instructions on how to sync Google Calendar with Apple iCal on the web at Google Help.  Although these instructions didn’t provide an exact step by step for how to sync with my iPod, it was enough to get me going.

Here’s how to do it on the iPod Touch (and I assume it is the same or very similar on the iPhone):

1. Click on the Settings icon on your iPod
2. Open “Mail, Contacts, Calendars“
3. Click “Add Account…“
4. Choose “Other“
5. Choose “Add CalDAV Account“
6. Enter the following information:
   • Server: www.google.com
   • User Name: your Google Account username
   • Password: your Google Account password
   • Description: anything you like, I like “Google Calendar” myself
7. Hit Next, and it will verify your account details, then return you to the Accounts screen
8. Scroll all the way down to the “Calendars” panel and click on “Default Calendar“
9. Choose the CalDAV Calendar that you just entered

Your iPod calendar will now automatically sync with your Google Calendar at the frequency you have selected in the “Fetch New Data” panel.  Set it to Push to have it go automatically (drains the battery faster) or choose a Fetch frequency.

This is an awesome addition to the iPod Touch and I’m look forward to using it!