21 Reasons Why iTunes Sucks
October 7th, 2003

Recently I endeavored to reencode my entire CD collection. Something I was loathe to do. I hoped never to do it again. So in that spirit, and with drive space being so cheap, I decided it made sense to reencode everything in AIFF format instead of Apple's format du jour, AAC. The reason for this is two-fold: sloth and quality.

Everyone should record their music this way. Well everyone who wants to avoid having to re-rip their entire library every time Apple or someone else comes out with a new encoder, like AAC.If you have your music ripped at full quality (unlike MP3 or AAC, AIFF is an uncompressed, full CD-quality format), you can just transcode your music folder to any format without re-ripping from the physical CDs -- well at least in theory. Also, you paid for the full quality of music on your CDs; you should enjoy it fully. To boot, nowadays, there is no reason to skimp on an encoding format when you can fit 500 full quality audio CDs on a drive that will cost you less than an iPod. For less than US$250.00 (as of a few months ago), I was able to buy a 250 GB hard drive.

Incidentally, with another 250GB drive, I also chose to image (using DMG format via DiskCopy) all my computer CDs. This easy backup method allows you to mount and access your computer CDs more quickly; it also solves the "lost CD problem" by keeping all your CDs at the virtual ready in one place, but I digress.

Although I chose the appropriate hard drive size for the job of reencoding all my music, I didn't fare as well in my choice of encoding program. Unfortunately, I chose iTunes. This swill sucks so bad, there just aren't enough invectives to insult it properly.

To be fair, iTunes serves as a fine search and play system for your music. However, iTunes proved itself to be a pile of crap wholly unsuitable for the simple "digital hub" task of importing music. This was truly surprising considering the overall excellence and high quality of both Apple's hardware and software products in general. Regardless, I cannot express my extreme loathing for this misery-inducing blight of a program and its odious import abilities (or rather, inabilities).

The problems were many (21 in fact), (aka How iTunes sucks, let me count the ways):

WARNING! WARNING! Attempt the following iTunes workarounds only at your own risk. You might lose all your music data. If you do, don't blame me. I do not recommend any of the procedures, below; especially not those requiring manipulation of your /Users/HOME/Music/iTunes directory. If the procedures do not make sense to you, you're better off not messing with iTunes. Otherwise, you're likely to obliterate your music settings. In other words, you're on your own. Caveat emptor. Objects in mirror are closer than they appear. Insert standard tushy-covering disclaimers here.


What you can do about it

1.   When iTunes would import AIFF files from a faster external FireWire CD ROM drive, it resulted in files with spurious skips.

Don't use an external CD drive to import if you want to ensure data integrity.

2. iTunes would rip AIFF files at slow speeds (4X-6X) from the internal (667MHz DVI) Titanium PowerBook (TiPB) Combo drive. On an old 500MHz Pentium III PC, Nero ripped AIFF tracks at much faster speeds (typically 16X). Note: the PC had an old CD drive with a speed rating equal to the TiPB.

Buy or borrow a faster desktop Mac or do it on a PC instead.

3. iTunes would not read all CDs from the TiPB's internal optical drive.

Nero read the problem CDs with no trouble on a PC. After encoding with Nero, I transferred the files to the Mac and hand entered the tag information because tags do not always follow AIFF files.

4. The PC would import album cover art through MusicMatch while ripping, but iTunes does not.

You can (a) paste in art by hand or use the FetchArt script to do it from iTunes (currently, it only works for MP3s and not AIFFs); (b) buy all your music with Digital Rights Management from the iTunes Music Store; or (c) live without the art you big baby.

5. When importing AIFF versions of MP3 music that you already have in your iTunes library, iTunes can lose both the MP3 file and the newly imported AIFF files when you confirm that you want it to replace only the MP3 versions.

Check your trash after every such prompt and hand drag the AIFF versions back into your iTunes library directory.

6. iTunes constantly obliterates library and play list settings when you re-add files to your library.


7. iTunes is incapable of transcoding your music collection on syncs to your iPod. It would be great to downcode full CD quality AIFFs automatically to 128 Kbps AAC files on syncs to your iPod, and maybe 224 Kbps on syncs to your laptop.


8. iTunes does not allow you to reorder its leftmost column heading. Why the hell not? I would like the artist column to be first instead of the intractable song title column.


9. Engaging the CD eject button puts the entire system into a conniption.

Bang head against desk while hoping multithreading becomes more than a buzzword.

10. If you store your music library on a FireWire drive, and if that drive becomes unavailable for some reason, then iTunes resets the library location to your home directory without telling you! When you later plug in your FireWire drive and import your next CD, iTunes will stash the music in your home directory instead of on your FireWire drive where all your music is supposed to reside.

Scream in agony realizing it will be easier to re-encode the last few CDs after resetting iTunes to look at the correct directory, than copying over the files, having iTunes re-organize the mess, and then having to scan through your library for duplicate files all while losing your metadata for each track. Learn to make frequent backups of your /Users/Home/Music/iTunes directory so you can undo import mistakes without threatening destruction of all your library metadata.

An alternative "fix" might be to delete all the song entries in the iTunes database library, move the misplaced songs into your desired target directory, and then have iTunes re-add all the files to the iTunes library. However, this will lose all your metadata tags not embedded in the files themselves, e.g., the number of times a track was played, etc. See item 6 above.

11. When you reset your default music library location that iTunes inappropriately reset (i.e., see item 10 above), you have to wait through "updating song locations," and file reorganization even if no files have moved and you are merely correcting iTunes' mis-set file location setting.

While you pass the time, imagine the programmer responsible for this having a really bad day.

12. Any false move will cause iTunes to reorganize your music files in only god knows what way; if you're not careful you may end up losing files because you don't know what iTunes is doing or where it might be placing your files.

Be super careful.

13. Why the hell won't it let you name tracks the way you like? The actual file names assigned by iTunes are just the track title and track number; neither artist name nor album title are used to name the file. This makes locating or consolidating files into a single directory difficult; there is a potential of different artists having the same song title, which cannot coexist in the same directory.

Use an excellent iTunes script called RenameFiles to rename your tracks. Unfortunately, when you have thousands of files, RenameFiles can time out; instead, use it on around 1,000 files at a time.

One terribly inefficient method to flatten the directory structure of your music (i.e., to have all your songs in one directory instead of in Apple's forced hierarchy), would be to use AAChoo. AAChoo is fine if all your tracks are in AIFF format, but reencoding your 64Kbps MP3 tracks as 128Kbps AAC files in one mass conversion (i.e., along with your AIFF files) will both waste space and result in further lowered audio quality. Hopefully the makers of AAChoo will add the ability to filter and/or skip conversion of specified files and/or types while converting others.

14. The transcode user interface is moronic. The transcode menu is under the Advanced menu in iTunes; but wait, before you highlight the tunes you want to transcode and select the menu, you must first set the output format. How? You go to the preferences panel and select the transcode output format under the import options.

Real intuitive; in Bizzaro world, maybe.

It would be more natural to have a dialog sheet presented asking you to specify an output format and a destination for the output files.

Scratch your head wondering why.

15. As if the transcode interface wasn't bad enough, it integrates miserably with your iTunes library database. As a bonus, iTunes intermixes the transcoded files with the original files in your iTunes library. Good lord, why? Does anyone want to have both versions in a single library? Whether you want it or not, congratulations, now you have two versions of the song in your iTunes library and no easy way to separate the transcoded version out from your original tracks

One solution is to backup your iTunes datatabase directory (/Users/Home/Music/iTunes), then change the location of your music directory in iTunes->Preferences->Advanced to your desired output location. Then select the format to which you want your original files transcoded under iTunes->Preferences->Import. Next, select the files you want to translate, and select the Advanced->Transcode menu. After the transcode is done, quit iTunes, and restore the iTunes database directory you backed up. Launch iTunes and reset your iTunes music directory to its normal setting. Wait for iTunes to update its database for no reason. Curse the programmers. Easy; yea right.

Alternatively, sort your iTunes library by the date imported column. Select the files that were just added through transcoding. Then use the MoveFilesToFolder script to move these files out into a single directory. Hope that none of the files have the same name and obliterate one another; see item 13 above for a fix and similar provisos.

16. Transcoding from AIFF files from one FireWire drive to another is slow. Amazingly, with no other applications hogging the CPU, a 667 MHz TiPB transcodes already ripped AIFFs to 128 Kbps VBR MP3s or 224 Kbps AAC files only at around 7.5X speed. MusicMatch on a 500 MHz Pentium III imports from the CD drive at 8X.

Buy a faster Mac or PC.

17. Transcoding in iTunes is unreliable for a large number of files. iTunes will just bomb for no discernable reason when you have it transcode a few thousand AIFFs (sometimes the bomb is so severe that it seems to have logged out of the account and re-logged-in). The transcode process does not log its progress, and does not necessarily transcode the selected files in any given order. What this means is you have to delete whatever files iTunes successfully transcoded, and start over because there is no easy way to continue from the point of failure.

Transcode around 1,000 files (or less) at a time to avoid this unreliability.

18. iTunes does not come with support for 3rd party plug-in encoders such as OGG, etc. Particularly saddening is the lack of support for any type of compressed lossless encoding format such as FLAC.

Mope around imagining how nice it would be to store twice as much lossless audio on your 250 GB hard drive.

19. iTunes is unable or extremely unresponsive when attempting to copy or move large numbers of files from the iTunes library to another location.

Here's a scenario. When adding music to iTunes, if you have the "keep iTunes files organized" option selected, it blithely renames your files and obliterates your nice flat file structure; i.e., if you had all your music is in a single directory, now it's in a hierarchical mess with file names that are too short and nondescriptive. You may think there is, but you will find there is no easy undo. Simply selecting all the files in the library and moving them to a directory doesn't work in practice. Try it and feel the beach-ball-cursor-from-hell-wait. Assuming your iTunes library consists of a few thousand tracks or more, when you try and select your entire library to move it from iTunes out into a single directory in the Finder, you'll first find that your system hits a brick as soon as you try to move the selection beyond the iTunes window. Why? My guess is the drag-n-drop code is far from optimized.

Next, even if you have the extraordinary patience to move your cursor over the Finder folder with the mass selection, you'll find that the folder will not highlight. You have to hold it there a long time; it might eventually highlight, it might not. Roll the dice. Next, even if you get the files to drop in, an iffy proposition, then you get to experience the joy of iTunes telling you it timed out in trying to execute that function. Further, as the file names are so short now, you run the risk of two songs (from different artists, but with the same name) obliterating each other. Something that is all too likely when you have over 5,000 tracks with artists covering each others' songs. As a special bonus, you'll have no easy way to figure out which one clobbered which.

There is no easy solution here. First, you might use the RenameFiles script to forcefully rename all your files to something more unique. Unfortunately, this script tends to time out when used upon multiple thousands of files. As such, you should limit yourself to a renaming a thousand files or so at a time. Similarly, after you get all the files renamed (making sure you kept the "keep my files organized" option turned off in iTunes or it will happily undo all your work), you can then try and drag and drop around 1,000 or so files at a time into the Finder directory. You could also use the PutThisToWhereIWantIt script, however, it also times out with large numbers of files, so the same caveats apply.

20. There is no ability to maintain multiple libraries. For example, iTunes is not smart enough to figure out you have a library of AIFF files on a FireWire hard drive, which plugs into your PowerBook at home, and an identical library in AAC format on the PowerBook, which would be used away from home.

Keep two sets of books. First, backup your /Users/Home/Music/iTunes directory. You can have one library by creating an iTunes directory that targets your AIFF filled external drive, and then another library that targets your MP3 files; e.g., the AIFF FireWire drive that stays home on your desktop, and the MP3s that travel on your laptop. After making a new library for each drive, you simply rename the one you want to use to "/Users/Home/Music/iTunes" and rename the one you don't want to use to "/Users/Home/Music/iTunesAIFF" or "/Users/Home/Music/iTunesMP3." If you want to get fancy, make an Applescript/Quickkeys Macro to swap between the iTunes directories from a hotkey. If you don't understand the above, then it's best not to mess with your iTunes directory.

21. iTunes does not support all or the most common and new CD burners. I just bought a new 52x FireWire burner. While Toast can see and use it without problems, iTunes blithely ignores it.

This is particularly bothersome if you plan on buying music from the iTunes music store. If you do, and you do not have an Apple blessed burner, your intractable DRM music purchase is effectively non-exportable beyond your Mac.

Buy a Mac with a burner and live with it no matter how slow. Alternatively, waste a lot of your time researching the select few drives Apple has "blessed" before making your purchase. Perhaps more realistically, dump another $100.00 on Roxio's Toast (US$89.99 from Amazon)
For a platform billed as a digital hub, this thing sucks. It can't easily transcode and move music from one device to another. Not even to the iPod. Forget about managing multiple libraries for different drives/machines and automatically synchronizing them. A digital hub should have the ability to automatically transcode down to devices that are more limited than your primary machine, e.g., PDAs, iPods and laptops. For example, it would be nice if iTunes would sync and transcode an AIFF based library for a desktop machine down to an AAC encoded library on your iPod. This would allow each machine to hold the best quality recording it can based on its storage constraints.

Forgetting these more sophisticated media management abilities, iTunes stalls, sputters and fails at even the most basic encoding and transcoding functions. More a dud than a hub. If Apple wants to truly become a digital hub provider, it should consider employing a real database in iTunes. If the file system, or at least iTunes, used a more sophisticated database to track files, iTunes might be able to cope with multiple versions of your media and keep track of it all, even at different locations.

Not Just iTunes

All of this applies not only to iTunes, but also to iPhoto (which wastefully makes way too many copies of your media), iSync and other backup applications. Currently, the nightmare problems of synchronizing user accounts and backups are left to the user to resolve. No wonder most people don't bother to backup. They don't know where to start. For even the most remedial of such tasks, iSync is useless. If a user has user accounts on a laptop and a desktop, iSync doesn't even attempt to live up to its name and keep them synchronized. Forget the more subtle, but still common problems of people having to figure out how to sync their Entourage/Exchange server mail, calendar, and contacts data with Mail.app, iCal and AddressBook.

For people working in corporate settings forced to use Entourage, they have only one real choice: dump the Apple products because there is no easy synchronization option. Syncing the system with Exchange should be an out-of-the-box no-brainer for Apple as it is a necessity in the corporate world; tangentially, it's a mystery why Apple's products don't interface directly with Exchange in the first place. Unfortunately, iSync is truthful in its descriptiveness of how synchronizations are best achieved. I sync them myself.

The bottom line is this. iTunes sucks for mass movement and/or encoding the files that will comprise your music library. In particular, if you plan on encoding in MP3 format (or some other format where tags are embedded in the file), you're better off doing it on a PC with MusicMatch 8; then copy the resulting files from the PC and add them into your iTunes library. Unfortunately, if you import in uncompressed AIFF format from a PC program like Nero, the tag data doesn't travel with the files. That forces you to use iTunes if you want to avoid entering the tag data by hand.

With that said, iTunes is still, sadly, the best MP3 player application. What makes iTunes better than, for example, MusicMatch 8 on the PC? Certainly not mass encoding. iTunes does excel at the most commonly used functions in an MP3 player application: searching, playing music, making play lists, and burning CDs (as long as you limit your burning to one of the few DVDR/RW or CDR/RW drives supported by iTunes). While iTunes raises the bar head-and-shoulders above its competitors in the area of user interface, it's inferior in almost every other way.

The end result is that months after I started on my reencoding journey, I still haven't finished the job. As if the original task of ripping were not made painful enough with the aforementioned problems, I still haven't managed to transcode the AIFF files into an AAC copy. The challenge of getting all my files well named and into a single directory for use on my PowerBook (without transcoding any intermixed non-AIFF files into AAC format) is seemingly beyond the capabilities of iTunes. My guess is few will be crying any tears for me, but everyone should be crying for Apple's execution on fulfilling its "digital hub" promises to unsuspecting music lovers.