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Defending the iPod against those who berate its ease of use and interface

There has been lots of discussion amongst the blogger fraternity about iTunes, iPods, Apple and misunderstandings.

The latter comes from the not infrequent discovery that music downloaded from the iTunes Music Store is not your's for life if you lose it. Huh? How do you lose it?

Easy! Your Powerbook hard drive dies, your desktop Mac burns in a household fire, you leave your iBook in a cab, or a thief breaks into your office and makes off with your Powerbook/iPod combo.

On Apple's website, there is clear advice about what to do to prevent the loss of your music: it's called creating a backup.

Every Mac now comes with recordable media, and the Powerbook's standard with DVD-R hardware. Most Windows boxes also come with recordable media.

They also comes with USB 2.0 and Firewire ports, allowing external hard drives to be used as back up devices; subscribing to .Mac gives a place to upload and store music; and .Mac provides a Backup application to automatically facilitate this, broadband preferred of course.

People who have lost their music files in any of the scenarios above and get upset by it, seem to be confusing licensing governing music files with application files.

When my Powerbook's hard drive died, I had just enough time to backup my documents created or worked on that day to external media. Much of my music was on my iPod, and most of it was also duplicated on DVDs. But some was lost. And so were applications I had purchased from the web.

Things like NoteTaker and Salling Clicker. Fortunately, my Mail contents had been backed up and so I could retrieve emails containing serial numbers. For one application, I emailed the developer, offered some ID, and was able to go to their website, download the application and key-in new security ID sent to me by email.

Savvy computer owners upset that Apple won't play the same game, seem to think that because they were receipted for their iTunes music store purchase, Apple knows of their purchase and should send them another file or at least allow a free replacement purchase.

I want to suggest that Apple treats the music download business differently from its software business. For the former, it has to do deals with the music owners, and for all that is publicly known, they may have agreed to a one download-no replacement deal to get the iTMS up and running.

I feel sympathy for anyone caught out who didn't know that all files need backing up, including music files. That directive from Apple exists on its website, but perhaps it could make it more obvious.

Now to discuss Dave Winer's criticisms. Dave asserts that although he is a professional software designer, he can't comprehend the iTunes interface:

"The user interface on iTunes is awful. It's the worst piece of crap I've ever used. People would tell me when I was a Windows user that it was because the Windows version of iTunes is crap but the Mac version is easy. Well, both programs are head-up-butt impossible to figure out. The user model makes no sense."

By way of example, he then asks several questions, in a rhetorical fashion for which there appears no answer.

Here are his questions:

When is something on the iPod? How many copies of the music do I have? Where the fcuk (sic) are they? How do you delete something? Is it really gone? Why does it wipe out the contents of the iPod when I don't say it's okay to?

So let's try to answer them. I'm no pro software developer, but I did studies in Knowledge Management so maybe that's why the answers come easy to me (although I was using iTunes and iPods two years before starting my course).

1. When the iPod connects to the Mac, its symbol appears in iTunes under Sources.

Clicking on the screenshot (right) will enlarge the image so you can see my iPod, highlighted in red because it is automatically updating. It actually flashes in red during the updating phase, which of course can be set to occur manually via iTunes Preferences. You can then manually drag song names in iTunes over the iPod icon.

Because my 60GB iPod has more than enough capacity to handle all my iTunes files, it is just easier to make the update automatic. I could also automatically update selected playlists if that was my choice. Again this can be selected via the extensive iTunes Preferences.

(I don't know about you, but after installing a new application and getting it running, I almost always visit its Preferences to check out what this puppy can do - or not.)

Notice too that the iPod icon has a triangle next to it, pointing to the right.

Clicking that points it downwards, revealing the iPod's playlists (below left).



Because iTunes' Preferences have been set to automatically synchronise everything, the iPod's playlists are the same as those for iTunes itself.

If I click on the iPod under Source, the list of files in the main iTunes window changes from the Powerbook's collection, to that on the iPod. In this case they don't always match, because there are some files I have manually deselected from being copied to the iPod. So even though the playlist names might match, their individual content might vary because I have manually deselected files I don't want copied over to the iPod.


Notice too that the files are greyed out, preventing me from manipulating the files manually, especially uploading them from iPod to Powerbook. It's strictly a one-way process, with the iPod acting the dumb slave to the Powerbook's iTunes, especially since I've set the update process in iTunes Preferences to automatically update.

Of course, you can smarten up the iPod with a variety of third party software, allowing you to reverse the process, i.e. iPod -> iTunes, such as the free, award-winning Senuti.

Senuti reverses the transfer process (iTunes backwards) and its author, sophomore Whitney Young offers the following as some explanation for its workings:

"There's a little file on your iPod called the iTunesDB file. What does that mean to you? Nothing. What does that mean to me? Everything.
Every bit of information on every song on your iPod is stored in this little file. Every bit of information on your playlists is stored in this file, too. It's how iTunes knows what's on your iPod. It's how your iPod knows what's there, too. There isn't a much faster way to figure out what's on your iPod."


This might also explain why after connecting your iPod it can take some time for its icon to appear in iTunes, ready for you to transfer files. Databases on the Mac and iPod are being compared, readying each for an accurate synchronisation. The more you have individualised the updating, rather than making it completely automatic, the more database comparing occurs, and the longer before the iPod appears in iTunes.

So to answer Dave's first question, yes, you can see what's on your iPod.

However, if you want to search your iPod using iTunes search window, you need to set the updating process to Manual. The point being in Apple's view, that if you automatically synch your iPod as SOP, then you might as well search iTunes itself.

If you want to be sure, then set the update to Manual, and iTunes will reveal the iPod's contents and you can then use its Search feature.

2. Dave's second question asks how many copies of music do you have in iTunes. In the past this was definitely a problem, and indeed I often have variations of the same music by the same artist, because they come from multiple sources, such as "Best of's" and Compilations.

With my Powerbook's hard drive nearing capacity, best to delete duplicates, so iTunes now includes a "Find Duplicates" menu item.



Click on the screenshot right, to see the Show Duplicates menu item, under Show Artwork and above View Options.

iTunes will then list all duplicates, one on top of the other, and at the bottom of the iTunes window there will also be another menu item.


Notice in the above example how Adam Green's files are showing up as duplicated, and note the annotation at the bottom of the iTunes window allowing you to go back to "show all songs".

In this case, iTunes was fooled, since these two files are not duplicates, as you can see by their different time lengths. So iTunes is operating on other ID tags, and in this case, Adam insufficiently differentiated the files by name and other virtues. Podcasters especially could help out their subscribers by carefully attending to ID tags.

The point is, iTunes will allow you to identify duplicates and do something about them, should you choose.

3. Dave's other question asks where the files are kept. One could search the hard drive using Spotlight, but that would be a less elegant although successful means.

Again, iTunes offers you a menu item under File, called "Show Files", with the keyboard shortcut of Command-R.

OS X will then open the folder containing the file in the Finder, and display it depending on how you have set up the Finder to display files (list view, icon, etc). If you want to be sure this is the file, you can highlight it, hit Command-I to bring up a long vertical panel displaying the file's parameters, and also hit an operator in the Get Info called Preview and listen to the file. This vertical get info panel displays at the top a "Spotlight Comments" field where you can add personal metadata for better searching Spotlight another time.

The same vertical panel will also reveal the file path. So Adam Greene's file on my Powerbook has the file path:

/Users/lesposen/Music/iTunes/iTunes Music/adamgreen.org/Adam Green's Software Stories.

4. Dave also asks how you delete files.

While not tricky, it does need some understanding. Remember iTunes stores files in its iTunes/iTunes Music/Artist folder. Let's say you download podcasts via an RSS reader automatically when they appear. You can set some RSS aggregators like NetNewsWire to automatically download, transfer to iTunes and then delete the original file.

In iTunes Preferences, you can set iTunes to either copy files into a folder in iTunes Music and keep a duplicate in its original download location, or trash that original file once you have copied it in. It's your choice.

Whatever the case, should you want to delete an unwanted file or outdated podcast, you can either locate it in iTunes, use Command-R to physically locate it, then drag it to the trash, or highlight and Command-Delete.

This is not recommended, because iTunes keep a database called iTunes Library, where it keeps track of your iTunes to make searching faster amongst other things. If you go behind its back by manually deleting, you will get an exclamation mark against the file's name in the main iTunes window. Which means a record of the song or podcast still exists in the database, but the real file can't be located.

Clicking on the song in iTunes will bring up a message box that looks like this:


Clicking OK will open up a Finder window to allow you to navigate manually through iTunes folders, or use the Search function.

If you want to delete a music file in iTunes itself you highlight the file, and hit... Delete on the keyboard. Or go to iTunes' Edit menu, and locate Clear to delete the track from its playlist or Library.


This brings up a new dialogue box offering you a choice. You can rid yourself of the file from the iTunes Music folder, or rid yourself of it from your hard drive, if you decided at the outset not to have iTunes bring all your mp3 files into one place.

Remember, at the outset, iTunes will scour your hard drive, and either leave them where they are, or bring them all into the iTunes Music folder. Again, it's your choice. This also answers Dave's question as to whether the file is "really gone".

Dave's last question follows an unpleasant event when he connected up his iPod to another Mac which wasn't the one he had used to synch in the first place.

It was his claim that hooking up his iPod to another Mac (his iBook) wiped out his iPod contents without asking him if it's OK to do so.

When I plugged in my partner's iPod Photo to my Powerbook, this is the dialogue box that appeared:



Notice the default in blue (what action would happen if you hit the Enter or Return keyboard key) is not to replace the visiting iPod's contents, photos, music and movies if it's a 5G iPod.

You have to manually select YES for this to occur, Dave.

Now because my iTunes is set to automatically update, those files not in common between Lili's Powerbook and mine (about 700 files) began to transfer from my iTunes to her iPod. So I quickly hit the eject button (there are two in iTunes, by the way) and no transfer takes place. The hint here is to always select Manual Update in iTunes preferences before you hook up another's iPod. You can also hit the STOP icon in the iTunes "what's playing" window and leave the visiting iPod still connected to charge or manually download.

Update - December 29: Special caveat: Use the Eject or Stop controls to prevent the auto. update adding new files.

Don't pull the USB or Firewire cable out of the PC or iPod, just as you wouldn't disconnect an external drive this way. You run the risk of destroying the drive's directory and thus wiping out its contents. It's happened to me once and only once wth an external drive - I learnt my lesson. But it is easy to panic and do this even though the iPod screen is flashing that STOP icon and telling you clearly not to disconnect. Or you can hack your "Do not disconnect" screen to look like this.

Should you try to download your purchased music to the visiting iPod, you need to set iTunes to manually update since the other iPod may not have a matching Purchased playlist. iTunes will allow you to download DRM'd files to another iPod not your own.

So Dave and others, I hope that answers your questions.

Some were obvious, while others did require some trial-and-error on my part, and are not for the newbie Apple user, or one used to the Windows way of doing things.

All the answers I have offered are documented on Apple's webpages even if not in the materials that come with the iPod, which perhaps they should be.

Update: Oh, by the way, Audiobooks, often divided up into chapters, came along after iTunes was first released. So in later versions of iTunes, a "grouping" feature was added to keep chapters playing in the correct order. This is also useful for stageworks, operas, and classical pieces with several movements.

So, Dave, you want to do more than the average user who just wants to rip CDs, download music and podcasts, and have a simple, almost one button operation to synch the iPod. In fact, leaving everything to iTunes automatically usually means merely using the USB cable to connect iPod to Mac and it will do everything in the background while you continue coding or surfing.

Apple's fame for its ease of use and HCI stand up pretty well, I think, despite your having difficulties. Happy to answer any more questions you might have.

Update December 26, 2005: While waiting for any acknowledgement from Dave, I do note via MacSurfer that Paul Thurrott's Internet Nexus webpage has taken up the subject of iTunes' interface.

He quotes for his readers of Dave's criticisms, which he describes as "fairly accurate".

He also desribes these questions as I have as rhetorical in nature, and uses the same term I have - berated - to describe the nature of Dave's and others' criticisms.

So I thank Paul for taking time out from his Christmas Day observances to blog about Dave and me, and to single out my "friendly" response to Dave amongst those in the Mac fraternity.

But you do know I will not respond in too friendly a fashion to the following comment by Paul:

"The fact that Posen's post is so long should alarm people. I think it proves that Winer has a point."

It's interesting how being so inclusive of material available in both iTunes' Help files and online support areas should cause alarm. I excluded a fair amount of helpful material and stuck to answering Dave's questions, elaborating so that others may also learn from Dave's questions.

That I was quite verbose and inclusive of illustrations should tell you as much about me as it does the program. I disagree that the length of my blog entry should be equated with Dave's criticisms being accurate. It's not, and his criticisms suggest he has not spent enough time with iTunes, perhaps being seduced by its seeming simplicity which so satisfy its millions of users.

No, Dave being the uber-programmer asks questions most users who simply want to use their iPod won't bother with. That's not a failing on his part by any means, but his struggle to transfer training means he has more to change than newbies do.

That my post is so lengthy means I wasn't interested in meeting a word limit - it's my blog after all and I can be as long-winded or terse as I please. Again, to equate the length of the entry with troubles with iTunes stretches rational argument in search of any evidence for iTunes' vulnerability.

iTunes is one of the most stable and rich programs on either Mac or Windows. I have colleagues who spend hours each night using it in DJ fashion to program dance sessions, dragging files and playlists about while the music is playing, and the program remains rock-solid. It just doesn't crash. Showing me another piece of free software aimed at the general public (unlike say, speciality DJ software like Megaseg or Traktor) which has its robustness.

Look at the richness of the program as it's developed over the years. It does require a lengthy reply because it is so feature-rich, not because it's poorly coded or has an inpenetrable HCI.

Let's look at a sample of what it can do:

1. Audio file jukebox with
- multiple playlists and smart playlists
- a random setting
- ID3 tags
- audiobook and multi-movement grouping
- equaliser settings per song
- user changeable entry and exit points per song

2. Video file juke box, playing either in a small window or full screen

3. Music Store, together with 30 sec sampling, uploadable mixes, celebrity mixes, and one of the easiest online shopping experiences around. After Amazon, the next biggest online shopping service.

4. Video Store

5. Podcast subscription service, which can be set automatically. Ability to "host" podcasts housed at other locations apart from .Mac.

6. Ripping CDs

7. Burning CDs and DVDs, the former as either audio or data CDs.

8. Converting between file types, eg., mp3, AAC, WAV, .mov, AIFF amongst others.

9. Sharing music on others Macs via iTunes sharing over 802.11x

10. Synchronising with iPods, manually or automatically

11. Parental settings to allow parents to "protect" children from online content concerns.

12. Streaming radio with multiple stations across mutliple genres, using preset stations or ones of choices via URL.

13. Album artwork, including chapter marks for podcasts, as well as printing artwork and song titles.

14. Visualiser

15. Integrates with online Gracenote CD database when ripping CDs.

16. Plug-ins architecture for visual effects and mp3 properties

17. Works with Salling Clicker to provide remote control using bluetooth and wifi devices such as cellphones and PDAs

18. Works with Airport Express to wirelessly play iTunes from the Mac to the hifi system of choice.

19. The ability to manage more than one iPod per iTunes installation. Let's say you have a 60GB 5G iPod and a 2GB nano for your workouts. iTunes can handle both. See a screenshot here. (With thanks to Sam Pullara)

Now please, Paul: Show me another free downloadable application operating on both Windows and Mac that can boast these features amidst rock steady reliability.

If anything, given its richness, I did Dave and iTunes a disservice with the brevity of my reply! Dave still has a gazillion questions to ask if he just patiently prods and probes iTunes.

UPDATE - December 27, 2005: Paul's webpage has brought many visitors to the site, some of whom have provided interesting comments, especially one about the richness of iTunes' keyboard shortcuts which I ommitted because I don't use them very much.

It was also quite shameful of me to omit, especially for someone of Dave Winer's status, how iTunes employs Applescript to expand its functionality. And it was greatly remiss of me not to refer users to Doug's Applescripts for iTunes webpage. Doug is the true uber-guru of iTunes, identifying its faults, discoursing with its Apple developers, and rather than berating, doing something about those faults or shortcomings by writing Applescripts.

Finally, I also note that Dave has updated his blog entry to acknowledge Paul's blog entry, and included a quote which uses my name and this blog. Dave shifts his gaze somewhat by acknowledging some of his perceived flaws in the iPod/iTunes might be due to Apple's use of DRM, but says that ultimately, as it was written on the Pres. desk, "The Buck stops here", ie it's Apple who looks bad when DRM causes troubles.

From my viewpoint, DRM only comes into play for two areas of use: the loss of songs purchased at the iTunes music store which are not backed up; and secondly, the one way trade between iPod and iTunes, unless you over-ride it with third partty software.

(The remaining update par. below has nothing to do with iTunes and is a reaction to another part of Dave's blog entry).

Dave concludes his blog entry by offering a lesson in blog etiquette and quality of discussion:

"BTW, the "imho" part is something most of my detractors leave off, as they say some pretty personally insulting things about me (they often leave off their real names too). That should factor into your thinking. If the people promoting an idea say nasty things about people who differ with them, and if they have to take their swipes anonymously, they must not have a lot to say that's substantial, and they clearly aren't willing to stand behind their own thinking."

Dave has yet to reply directly to me via email, in this comments section, or via his blog, from what I can see at the time of updating.

IMHO, that's poor form if you see blogs as a form of dialogue. If you don't reply to people who take time out to patiently answer your questions more pleasantly than most - or even acknowledge their efforts - it's not surprising others will take a swipe anonymously.

Is there a grudge you're bearing, Dave, from some previous slight slight?

Update - March 23, 2006: The How Stuff Works Website has offered up a quite comprehensive page looking at all manner of interesting iTunes material, how-to's, background info., and what works and how it does!

Go here to see Julia Layton's impressive contribution.


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