iTunes – Terrible, iPod Shuffle- Nice aka I’m Windows Media Player and I’m an iPod Shuffle

Disclaimer: This post is about my terrible experience with the iTunes software and the synch process.

I am a regular buyer of original CDs and I survived on digital copies for my music fix. My Windows routine was as simple as 1-2-3.

  1. Put in a CD into my PC and run Windows Media Player
  2. The CD details was provided, I confirmed the correct information was displayed and proceed to rip the CD into my external hard disk.
  3. Play my ripped WMA files from start to finish.

It was a good routine. End of the day, I get my new CD ripped in a digital format I can take everywhere with me. Nice and flexible.

My iTunes routine

1. Put in a CD into my PC and run iTunes.
2. After verifying the right CD title was displayed, I agreed to rip the CD into the iTunes Music Library.

Issue 1: iTunes Music Library by itself does not allow me to move the ripped files around easily. I don’t even have the flexibility to determine the location of my destination folder.


3.   The source CD rip sequences was correct but the end results looks disastrous.

Issue 2: Tracks from the same album are scattered everywhere within the iTunes Library. What’s worst, iTunes Library don’t allow me to reorganised the scattered files.

I need my music collection organised. I cannot tolerated have orphan files scattered throughout my library. I’m not going to re-create a playlist for an album which I ripped from start till end.

The conversion speed from CD Audio to ACC (the only format supported by iTunes) is much slower compared to WMA conversion.

Please click on thumbnails for enlarge version.

4. Insert my external hard disk to convert more WMA files into iTunes Music Library. Duh! The USB external hard disk cannot be detected or seen in Windows Explorer. Need to use regedit hack from Microsoft KB to “recover” my USB hard disk.

Issue 4: I have to hack my registry each time to “recover” hard disk detection upon insert. I can’t do it everytime I use iTunes!

Guy clipping iPod shuffle to his sleeve

End of the story, I really like listening to music with my iPod Shuffle (Gen 2). It’s a beautiful device, the Al (wiki) casing feel so cool and sexy to hold.

 Ugly Step Sister iTunes

However iTunes v7.0.2.16 is like the fat, ugly, slow step-sister (like in Cinderalla) and inflexible piece of software crap. It limits my flexibility and makes it hard and longer for me to get my music in digital format and limits them to 1 location.

Any iTunes regular users have any insight to share with me on how to solve the scattered files problem?


7 thoughts on “iTunes – Terrible, iPod Shuffle- Nice aka I’m Windows Media Player and I’m an iPod Shuffle

  1. I wouldn’t exactly call myself an expert on iTunes but many of your problems are easy to change/fix.

    First of all you can rip music into other formats than aac (which is a good idea in my eyes). The best way to go is rip in mp3 format, that way your music will work in all media players, windows or otherwise. to do this in iTunes click edit – preferences – advanced tab – importing tab, then select mp3 from the drop down box.

    Along the way to doing that you may have also noticed under the advanced tab that you can set the destination for the music being imported and if itunes organises your music for you or not.

    I’m not exactly sure what the issue is with your external hard drive, is the problem related to itunes or are you just having trouble with the drive?

  2. Previously, Windows had no problems detecting that external usb hard disk (HD) until I installed and started using iTunes. Since then, the HD would not appear under My Computer.

    I will undo the “let iTunes organised your collection” option. Thanks for the tip and visiting my blog today.

  3. I have undone the option to let iTunes organise my library. I am still experincing scattered files acround my library. Grrr, I might need to grab a iTunes user in person for some guidance.

  4. Here’s what happened to me. I too bought the new clipable PINK ipod shuffle:

    “Dear Apple,

    I have just given my Valentine’s Present to my girlfriend, which is an Apple ipod Pink Shuffle.

    However, we were GREATLY DISAPPOINTED by the terrible quality of the product:

    1/ There is no “disable automatic sync. function” like on my bigger ipod.

    2/ I have read that we cannot use the ipod between our PCs. My girlfriend wanted me to use my PC as hers is broken at the moment. However, it seems that if I choose to do that, then she can’t use her ipod on HER PC later.

    3/ I had to manually install a new version of itunes for the ipod shuffle. There was no option to update my existing itunes software after being told my existing version wasn’t new enough for the shuffle.

    4/ NO itunes software came with the shuffle. It wasn’t even available in the shuffle itself. This is terrible as many users may not have access to the internet.

    5/ The itunes will change the music on her ipod every time she connects it to itunes.

    6/ itunes itself is NOT user friendly and other non official alternatives will not work.

    This is unacceptable and quite frankly I am EXTREMELY ANGRY with such a terribly implemented design. This has RUINED my girlfriend’s Valentines Day as she was really looking forward to using her ipod and I was looking forward to giving it to her.

    Therefore I expect you to arrange for the ipod to be picked up and sent back to you and I expect an FULL and TOTAL REFUND of my money, including delivery costs. At NO POINT was I told of the problems concerning this product, such as the lack of manual sync. features etc.

    I also expect a full and unconditional apology from your company for the terrible customer support.

    I am an existing ipod owner but I will now sell my existing ipod as I normally use my PSP. It’s MUCH easier to use and can be used on a variety of PCs WITHOUT any additional software.

    Please respond quickly as I want my association with your company to be over as quickly as possible plus I want my money back.

    Failure to respect my wishes as a customer could/willl result in appropriate and/or legal action being taken, to the fullest degree.

    Yours Faithfully,

  5. I’m not too fond of iTunes either, Primal Convoy. I’ve also got a 2nd gen Shuffle, but synching with iTunes is PAINFUL *sob*

    Another frustrating thing about iTunes adding to PriCon’s list, besides the fact that it takes forever to load on my computer compared to JetAudio or WMP, is that some of my music won’t go into the chronological order of tracks when I click on the “album” tab… “1,2,5,6,7,4…”

    Yes it DOES go in the correct chronological order when I click the “tracks” tab, but when you have more than one album… “1,1,1,1,1,1,1,2,2,2,2,2….” AAAA

    I’ve NO idea what I’m doing wrong… album name and artist are all right.

  6. i have 3 playlist on ma ipod clasasic.i tunes would allow me manually arrange 2 of them but third, no way in blue blazes.can anyone help me fix this cos its irritating tobe enjoying a particular trend of music only 4 it to b intercepted with some boring track which u wlda preferred being last track

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