by Bill Snyder

5 Fixes for iTunes’ Famous Flaws

Jan 03, 2011
Consumer ElectronicsMobileSmall and Medium Business

Apple's iTunes has it's flaws and isn't nearly as flexible as it should be. There are ways to fix some of the flaws via free or low-cost add-ons, here are five of the best options.

The iPod is certainly one of the best consumer electronics products of the last 10 years. iTunes, though, not so much. Apple’s software isn’t nearly as flexible as it should be, especially when collections get large. Some of the problems result from digital copyright issues, others from Apple’s unwillingness to play nice with other formats and devices.

Not surprisingly, there’s a cottage industry devoted to fixing some of those flaws with free or low-cost add-ons. Here are five of the best:

Tune up

I don’t know about you, but my iTunes library has way too many songs called “Track 01” or “Track 02.” That’s because when you rip songs from a CD, especially one that’s second generation, the album info and art are sometimes lost. That also can happen when you buy music from a site other than iTunes. A handy utility called TuneUp can correct that.

TuneUp launches itself when iTunes does, and shows up as a vertical window alongside it. TuneUp does a number of things, but cleaning up the library is what makes it worth having. If you download the free version, TuneUp will fix up to 100 tracks and retrieve the album art for 50 songs.

Although my library had several hundred unlabeled songs, TuneUp churned through the list pretty quickly, correctly labeling scores of tunes before I ran out of free fixes. There were only a handful of titles it couldn’t find in its database. It was successful in finding missing album art for many, though not all, of my unadorned songs. I have to admit that my musical tastes are fairly conventional, so maybe my collection wasn’t particularly challenging for TuneUp. But other writers say the database does well with more esoteric selections as well.

A full version of the program costs $30; a one-year subscription goes for $20.

TuneUp’s other functions are less impressive. You can expand your collection and share music with friends and be alerted when an artist in your library has a performance scheduled nearby. I wouldn’t pay for those functions, but $20 to cleanup up hundreds of songs is a good deal.

iTunes Export

Anyone can buy a CD or a gift card on iTunes. But there’s nothing like making a compilation tailored for someone you care about. Sadly, iTunes doesn’t make this easy. It’s awkward to export playlists you’ve constructed. iTunes Export makes it easy to grab a playlist you’ve built in iTunes and copy it and the songs themselves to a USB drive.

iTunes Export will copy playlists in formats that players other than iTunes can read as well. It’s free. And it’s very easy, as long as you download the GUI version. The other version works from a command line and is probably much tougher to use, though I didn’t try it. When you configure it, be sure that it’s looking at the iTunes XML file that’s on the same drive as the music itself. Otherwise you’ll export the playlist but not the songs.


Songbird is a cross between a browser and a music player that’s fun to use and adds value to iTunes.

During installation it’ll ask if you want to load your iTunes music directory or another media directory, or perform the task later. It loaded my library quickly and accurately. Playlists take an extra step. Create a new playlist in Songbird, highlight the songs in your iTunes playlist and drag them over. The Songbird interface cleaner than iTunes and quite easy to manage.

You can import bookmarks from other browsers, and use Songbird as player of songs you come across on the Web. It has lots of extensions and add-ons, though it appears that the built-in functions for Shoutcast and another streaming music site don’t work. However, that’s easy to work around by simply browsing to those sites with Songbird and bookmarking them.

Songbird also supports CD ripping; like other services it will notify you when artists in your library are performing in your city and it will track their new releases. Since Songbird is built on open source, it’s easy for developers to come up with add-ons and extensions, and there are lots of them.

iTunes Sync

Want to give music to a friend whose MP3 player was not made by Apple? iTunes Sync will let you synchronize your playlists with almost any MP3 player that shows up as a drive letter in Windows when you attach it via a USB port. (Microsoft’s Zune is an exception.) You can configure as many different MP3 players as you need and synchronize each one with a different iTunes playlist. Be sure to back up the target MP3 player before you use this program for the first time because things can go wrong any time you sync a device for the first time.

iTunes U

Strictly speaking this isn’t an app or a fix, but since iTunes U is so useful, and for some reason, not widely known, I’ll include it here. Apple and dozens of major universities have collaborated to make huge amounts of course-related audio content available for free via iTunes. Simply launch iTunes, go to the store, and search for “iTunes U.” When it comes up, you’ll find podcasts from many universities, and resources geared to lower grades as well. The university content is astonishingly rich. Go to Stanford on iTunes, for instance, and see offerings like Global Geopolitics, which includes ten lecturers, or a seven-lecture mini-course called The Future of Human Health.

San Francisco journalist Bill Snyder writes frequently about business and technology. He welcomes your comments and suggestions. Reach him at

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