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Published 27th April 2008 by

I finally succumbed to peer pressure and joined the digital media bandwagon by buying the latest Apple iPod Nano complete with iTunes. Here are a few tips for windows users to get the most from iTunes.

I have already ripped all of my legally purchased CD's onto my hard drive for a more convenient catalogue and playback through Windows Media Centre (which does a fantastic job BTW) so I just needed a portable device - and why not go for the king of MP3 players?

iTunes - Worst Software Ever?

iTunes - Worst Software Ever?

Upon arrival, the small, neat, packaging presented a shiny new iPod in a well-made perspex display case with everything packed in tidy and efficiently - the sign of things to come? The first thing I did was to turn the iPod on. Having never used an iPod before I was a little uncertain about the location of the on/off switch but when I pressed the menu button the screen lit up with a welcome sign prompting me to select my language. With that done I set about navigating the menus using the touch wheel - it took some getting used to! I find it a bit too sensitive and often move off the intended item while pressing enter.

Now I need some music on my iPod, so I headed over to Apple.com to download the latest iTunes software (my iPod Nano did not come with any) so when that finally downloaded (~60mb) I installed it and started it running, choosing a folder for my existing mp3's and let it go away and locate everything.

At this point, I must say that I was expecting it to search through the folders finding mp3's and cataloguing them in the same manner as Windows Media Center (WMC), that is it reads the MP3 tags for album/artist/genre and shows the album art.

Boy was I mistaken! I don't know what it did, but after half hour of disk thrashing I had over 2500 "albums" each with 2-5 tracks in them, some duplicates, most of the cover art was missing and everything filled under the "Other" genre. Most of the tracks had the wrong titles and albums were split up into multiple sections. The whole thing was a mess, then the program crashed.

After a bit of scouring on the web, I found that iTunes is very finicky about the tags in the mp3's and that it isn't intelligent enough to spot an extra space in an album title for example (unlike WMC), so I set about going through each and every mp3 with Windows Explorer and verifying the tags. With that done, I went back into iTunes, cleared out the library and started again. It processed most of the items correctly this time, but around 800 songs were not assigned to an album or artist, so I went through and re-assigned everyone from within iTunes.

Feeling good, now that I had sorted this out (after two days of playing with files) I started copying the files onto the iPod, but I noticed that there were a few albums missing, and I had only got to 'C'. A quick glance at the stats showed 2453 tracks listed - a little short of the 6825 mp3 files reported by Windows Explorer.

I set about manually adding these files into iTunes without luck. Apple has a policy of graceful erroring, so that if an error does occur - you don't know about it. At least Windows tells you that there was a problem importing a file!

After more net browsing I found a tip about stripping all tags from a mp3 then importing it, which does seem to work, but I now have to retag nearly 4500 files! And worse still - WMC is now totally screwed up because the tags have been changed by iTunes!

iTunes has just crashed again, and now it takes around 3 minutes after clicking on the icon to load up.

Four days of editing tags, assigning albums/artists/cover art and I still have not put anything on my iPod! Worst software ever!

So after all of this work, was it worth it? Well my new iPod Nano now has over 100 albums on it (1300 tracks) and I can now listen to my favourite music where ever I am.

Tips for Using iTunes for Windows

While tagging, converting and generally taking a long time to use a horrible piece of software to perform what should be an easy task, I learned quite a bit, including how to solve some very annoying problems.

iTunes will not import an MP3 track(s) - Firstly make sure you can play the track(s) using Quicktime player, if you can then iTunes does not like the MP3 header or tags. I used a tool called MP3 Repair Tool and removed the first 1 frame as well as everything after the last frame. iTunes would then import the file and you can set the tags manually.

iTunes will not import an album - As above, MP3 Repair Tool can work in batch mode. You can then use Windows Explorer to batch tag the files with album/artist by selecting the files, right click and select properties. On the Summary tab selects Advanced and give the files album and artist. This will group the files in iTunes where you can further name and tag.

Adding Album Art in iTunes - Not as intuitive as Windows Media Player, it took me a while to find how to do this. Select and right-click on the files to have art associated with them. Click on Get Details, and drag a jpeg image onto the artwork box. When you click on ok, iTunes will add the artwork to the files. Don't use a high resolution (I found 100x100 a good size) image as it will be added to each file. Large images will a) take ages to process and b) increase file size and album size meaning less can be stored on iPod.

iTunes splits albums up into separate albums of the same artist/title - You need to make sure that the artist and album are EXACTLY the same for all tracks. Select all the tracks that are on the same album, right click and select Get Info. Make sure that the album/album artist/artist is correct and tick the checkboxes next to them. This will tell iTunes to apply these settings to all selected files. If that still does not group them together then select them all, Get Info and change Compilation to Yes and apply the changes. They should now be together on one album.

iTunes takes ages to load - Still waiting to find a fix for this one. Each time I load iTunes it takes around 5 minutes for the program to show, even though I only have around 5000 tracks. I know people with twice this in iTunes which loads instantly.

Have you got any iTunes or iPod tips to share? Please share by leaving a comment on this post. Thanks!

45 thoughts on “iTunes – Worst Software Ever Written?
  • 15th October 2018 at 12:00 am

    iTunes is biggest pile of shit in universe and that should go into Guiness records. Every time I have to use it I need to physically prepare for torment that follows. "Making idiots from highly paying users" - should be their motto.

  • 23rd September 2016 at 12:00 am

    I think it would be difficult to find software which is worse than I tunes. It is completely obscure in its operation you have no idea what it will do to your data other than that whatever it does will be a disaster.,
    I unlocked my phone from T-Mobile which meant backing up to I tunes resetting the phone to factory setting then restoring from backup. As a precaution I backed up to icloud and to my computer. Unfortunately I selected the option to encrypt the data. This does not come with any warning that this option on restore will ask for a password that you do not set and make your data completely inaccessible. After a wasted day I finally managed to recover my apps and most of my data from icloud, although some of my photographs are not accessible.
    I tunes is the best reason to change to android devices.

  • 19th January 2016 at 12:00 am


    Still the worst program mad by man.

  • 20th January 2015 at 12:00 am

    Well, what can I say... Today I just bought an iPhone6 and was forced to use this HUUUGEEE piece of S---H---I---T. Fought for about 7 hours trying to sync movies and apps, unfortunately with no succes at all. So, as quick as I bought iPhone (today) as fast as I will give it back to shop (tommorow) and exchange for an android device instead (Samsung Galaxy Alpha? ;)). Such a lovely device (iPhone) with SUCH a HUUUUGEEE crappy software. Shame on You, Apple. Was happy becoming an apple device user, however, after one day (sic!) of using it ALONG with absolutely NECESSARY (to do anything on and with Your iPhone) biggest piece of software crap I ever used, I am happy that I will get rid of it tommorow... Apple, re-think Your strategy

  • 10th April 2014 at 12:00 am

    Man, you're the first Google result for "iTunes worst software ever" And this thread started in 2008. SIX, count them, SIX years later and iTunes is still the worsts software ever. I'm writing this after my third attempt to copy some photos and movies to my iPad on a fully updated and patched W7 machine.
    iTunes crashes more times than the ones it works. The dialog box "iTunes has stopped working" is now so much of a part of my desktop landscape that I barely notice it. Because you never, ever get a clue of what went wrong. You just try again and cross your fingers. Delete your photo cache and cross your fingers. And so on, until it works. For some reason.
    iTunes. Worst. Software. Ever.

  • Daniel Smedegaard Buus
    29th June 2013 at 12:00 am

    Yeah, definitely, this is the worst piece of crap every written. Even when it works as intended, it's illogical and utterly frustrating.

    It's like a big fat bully kicking you in the balls repeatedly, yelling "Stop kicking yourself!"

    I try to avoid it at all costs, but even if I just try to play back 10 MP3s, now in June 2013, it'll fail even at that.

    It's utterly amazing. To think they can make this crap. To think people will accept this shit. To think they'll call it good. To think they'll recommend it to other idiots.

    Sucks to be a Mac owner (mostly, I do actually love my Air)

    • 12th January 2014 at 12:00 am

      Agreed - Microsoft gets such a hard time for software and some of that is warranted but they BAR FAR make better software and actually stuff that you can understand and does not SCAM you into buying the SAME DAMN song over and over again because you can't get songs onto your device or computer. Its an utter joke. How can major apps just crash over and over. There is the reason the number one software program on mac itself is Microsoft office. Google is better but not far off - they just allow real programmers to fix the stuff by allowing you do what you want (cracking the device).

      please people take off the Apple colored glasses and see that this company is like any other company except they are promoting the zombie apocalypse to these UX wannabe baristas out the who keep buying iphones. DIE APPLE!!! And take Kucher with you. I had to buy software just to get my old songs off of my ipod unto my computer again. Why would iTunes not allow this. hmmmm I wonder why. BTW Jobs gets a movie and was the biggest douche in the universe exploiting Asian child labor and Bill Gates gets all the hate and he is spending every dime trying to feed the world. The world really needs to get their facts straight and stop watching the kardashians. ok off my soap box.

      the ONLY reason I have an ipod is is SMALL. That's it. Apple stick with hardware and let Microsoft build the software please.

  • 26th February 2013 at 12:00 am

    Worst software ever, i mean come on what's with this sync crap, it baffles me why you would make a simple process as irritating as possible. It should just be drag & drop, highlight and delete, but no i found i had to check a box to manage my music manually then uncheck what i didn't want. Seriously who thought this was a good idea and what amazes me the most is millions of people using this software and it's just a normal thing to them, either they never had a MP3 player before Apples products came along or they just really enjoy the monotonous task of using iTunes.

  • 30th January 2013 at 12:00 am

    ITUNES/IPOD is total rubbish. I am at the stage now of taking a bloody great hammmer to my IPOD as pretty as it looks!!

    I bought MUSIC stuck it on the IPOD together with CD's I owned and now after the latest download of itunes it says my laptop is not authorised to play MY alreday paid for music! I bought it long ago when I had a different email adress, can't remember the password etc etc. So now what?? JOBs! utter crap!! RIP.

  • 28th January 2013 at 12:00 am

    I upgraded to iTunes 11.
    The interface completely changed.
    It seems only music is important but I have an iPhone, I do not want music!
    Apps seem to be hidden in the store part of software but very difficult to find.
    Still not certain if it is wise to connect my three different iphone products to one computer. What is being synchronized to where? Will the IOS 4.3 apps also synch to my ipod 1? They seem to do so. Useless.
    Where can I find my contacts in itunes 11?
    Now I want to upgrade my phone but I have to transfer purchases?
    I already lost all my music files when iTunes 11 refused to connect to my iphone and I had to delete some file using a "backdoor" application.

  • 12th December 2012 at 12:00 am

    why can't they make itune user friendly

    it has been out there for year

    we should all demand that they should refund our money for any apple hardware we have such as ipod ipad etc.

    apple has to be the worst company in the world for supporting software

    the worst software ever developed; it is a nothing but fraud fraud fraud

  • 4th December 2012 at 12:00 am

    I have delete all apple programs and my apple 4s is my last Apple Brand. Why do Apple hate iTunes users, the old version was much better than the new. Goodbye Apple time to change to Blackberry or Samsung. %$#@#$%&%$$#@ s----h----i----t rotten Apple

  • 13th November 2012 at 12:00 am

    If iTunes was a man it would be a sad, unloved, moronic little weasel of a man. Going around making snidey little comments to ruin peoples' days and just generally being intolerable. Not even his parents would feel any shred of love, or even a lack of disgust for him. He would have the worst banter imaginable, would sell his grandma for a penny; only, no one, not even the lowliest glue sniffing, Jeremy Kyle guest appearing, common thug would do business with him.

    I absolutely detest iTunes!

  • 11th October 2012 at 12:00 am

    iTunes WORST JUNK EVER...too bad I still have to use it to use my iPhone.

  • 22nd May 2012 at 12:00 am

    I won't repeat everything that has been said about iTunes but I agree with you all. iTunes has to be the worst ever Windows app I have struggled to use. If anyone is interested, I am trialling JRiver Media Center and so far it is a dream to use. No more tag problems, no more duplicates, no more cover art problems, no more crazy filing issues and best of all it syncs my iPod without fail. It isn't free but I think I will buy it!

  • 31st October 2011 at 12:00 am

    One more:
    "The backup of <your device> failed because the backup session failed"

    That even makes the frequent "unknown error <some silly number goes here>" seem like making sense.

  • 30th October 2011 at 12:00 am

    I'm just looking at Android phones now; once I have found the right phone, I'll be putting my iPhone straight on Ebay, having unsuccessfully spent nearly 12 months trying to sort out my music collection on it. How come Apple can get away with such a flawed and badly designed piece of software? I've used many applications over the years and even the first generation MP3 player software wasn't half as bad as iTunes!

  • 14th October 2011 at 12:00 am

    I thought I was just being a doddery old fart when I felt frustrated at the monstrous complexity of the itunes interface. The iphone is great, but being forced to use this hideous program in order to have one is utterly disgraceful.

  • 21st May 2011 at 12:00 am

    Yes, this thread is old, but iTunes is still the WORST SOFTWARE out there (right beside Lotus Notes, but this another discussion)!

    Right now it's version is 10.2.2 and everything about is still pita like a 0.2.2 version.

    I do like my iPod, but the guys who made iTunes failed as one can fail.

    • 28th July 2011 at 12:00 am

      I've never posted on a site like this before but am looking something to put my fist through as an expression of how much I detest iTunes... as a software engineer I want to kill myself as a result of any association to whoever is responsible for it... I'm embarrassed to live on the same planet as iTunes.

  • 4th May 2011 at 12:00 am

    Agreed, I feel sick whenever I even think of having to use such an incompetent hunk of junk.

  • 2nd March 2011 at 12:00 am

    The best solution: DO NOT BUY AN IPOD!!! Get yourself a generic mp3 player and just drag n' drop the files into it! Isn't windows explorer great?

  • 21st February 2011 at 12:00 am


    An Apple a day ruins your life.
    If you have an iphone. You want to backup your contacts on your computer. You plug the iphone to your computer. You click "sync". What happens? Does it copy your 300 contacts to your computer? Or does it copy the 0 contacts from your computer to your iphone? Well, it copies the 0 contacts from your computer to your iphone, AND removes all the contacts from your iphone. So, instead of backing up your contacts to your computer, it removes the contacts from both locations. Amazing right?

    • 31st October 2011 at 12:00 am

      As sad as it is, this made me laugh for hours.
      Yes, inconceivable. True though based on own experience. I have never before seen somebody describe this moronic behavior so extraordinary well.

  • 25th December 2010 at 12:00 am

    I was lucky enough to not even have to use itunes. My wife bought me an ipod touch 4th gen this christmas. I could not even use the ipod touch because itunes would not pick it up so ....there my ipod touch sat with a stupid usb plug icon pointing to that idiotic itunes logo. I spent 3 hours on the phone with tech suport and still could not get itunes to work. I returned a perfectly good ipod because of the crap software the apple rams down your throat. Thats how bad itunes is. I refused the ipod because it is useless without itunes.

  • 6th November 2010 at 12:00 am

    Have a macbook air. All the software that comes with it works great - EXCEPT ******* ITUNES!!! It just took 9 and a half hours to add my music collection which resides on a nfs file share. Why does a company who puts out such innovative and good quality products have the worst software in the known universe in which to connect to them. YES, APPLE - (we are not all idiots out here) ITUNES NEEDS TO BE COMPLETELY RE-WRITTEN. Please take your Itunes programmers outside and execute them. Thank you.

  • 2nd October 2010 at 12:00 am

    iTunes suuuuuuucks... soo slow... crashes everytiime I run it... 30 minute install...

  • 14th July 2010 at 12:00 am

    I agree with everyone I got an iPhone I love it and it's a great product but eventually I started to remember y I never bought an apple computer all because of their restrictions lol really how much freedom do u got when u use an apple product I got a 32 gb iPhone 3GS and I can't even put 1000 tracks on it without some stupid error from iTunes telling me there's an error, I started using media monkey and all was good untill I upgraded my iPhone to os 4.0 which blocked media monkey from syncing with my phone and the last time I plugged my iPhone and started iTunes it changed my apps erased my music and pictures. The problem is that I didn't even have it on auto sync so I spent 2 days trying to get my stuff back on my iPhone and still no luck.

    I hate apple products and I'm just going to hack the crap out of this iPhone to take the chains off that apple has put on me

  • 24th June 2010 at 12:00 am

    I totally agree itunes is and always will be the worst software for PC ever made - try upgrading the iphone omg what a nightmare

  • 10th June 2010 at 12:00 am

    I thought I was crazy until this moment. Thank you all. And for the record, I Googled "iTunes is the Devil" and it brought me here.

  • 3rd April 2010 at 12:00 am

    The funny thing is we're spoilt for choice about what fundamentally retarded aspect of itunes to complain about. It's so pathetically useless it's almost hard to fathom! Frankly I think Apple deserve a 'Darwin award' for it. I would struggle to create something this bad if that was my GOAL!

  • 6th March 2010 at 12:00 am

    I just got an iPhone and love it! But iTunes is the worst program I have ever encountered. Absolutely awful. SLOW, cumbersome, unintuitive, extremely restrictive, and non-functional. I am purchasing a new laptop soon and was debating between a PC and a mac. iTunes has definitely steered me away from a mac.

    • 7th March 2010 at 12:00 am

      I've used itunes on a mac and it is better. It only seems to be Apple software running in Windows that causes a problem.

  • 11th December 2009 at 12:00 am

    Get over yourselves, if you don't like the software then don't use it.

    Get a Sony mp3 player instead and try get on with the shit software they produce.

  • 4th December 2009 at 12:00 am

    I've tried iTunes from version 4.x and with every single I tried, I was amazed at the problems I encountered trying to import my existing mp3s. I just installed version 9.0.2 to use a Airport Xpress for playback, tried to copy a album folder to iTunes and the damn thing just froze again. After all these years. Where does Apple think I keep my data? On my notebook? The whole concept behind iTunes is wrong.

  • 21st September 2009 at 12:00 am

    I boycotted iPods solely on the basis of this software. I then got an iPhone, tried some alternatives to iTunes, and nothing really did the trick, so I gave in and started using the software. Not only were my previous feelings reinforced, but elevated to a whole new level of frustration... to the point where I will stop virtual strangers mid-conversation, and seemingly arbitrarily ask them if they are aware that iTunes is the devil.

    Not only is it the most inflexible software ever, but it is one of the worst performing interfaces I have ever had the displeasure to use. Apple should be embarrassed to have their name on this product. With so many "geniuses" on staff, you would think that one of them could have engineered a halfway decent solution in which to imprison all of their customers.

    If the iPhone wasn't so great (other than it now repeatedly powers off after update 3.1), I would gladly continue my boycott of iTunes and all other Apple products, breaking my shackles of this inhumane software bondage.

  • 2nd August 2009 at 12:00 am

    Completely in agreement with everything said and just need somewhere to vent my frustration, because i am FORCED to use this software with my iPhone! Such a poorly deigned and poorly conceived program.

  • Martin
    5th July 2009 at 12:00 am

    i must agree with everyone.

    iTunes is the worst music software ever created !
    and dont think it run better on a mac, coz it don't !!

    i wish that Apple would make the iPhone protocol an open standard, so that developers like me, could make a .NET application for sync'ing the iPhone.... then i could make a player/program which would be 10000 times better then CrapTunes

  • 30th June 2009 at 12:00 am

    I'm guessing that most people stumble across this blog after a Google search similar to:
    "itunes worst program ever".
    And their sole intention would be to bash itunes somewhere. Well may I jump on that band wagon in saying:
    "if itunes was a person, and that said person was on fire, and my bladder was full of fire-extinguishing urine, I wouldn't even piss on said person".

    Dammit why is the iphone so damn good!

    • 30th June 2009 at 12:00 am

      btw, Google returned a thread from apple.com, so I thought I'd have a pop at itunes there, but when clicking the link I was redirected to:

      I dunno if this link will still work for you, but basically the discussion forum is down. There is a stupid animated gif that goes round and round giving the impression that something is loading. May I suggest that this is much what itunes does when it's obviously crashed after doing something extremely complicated like transferring more than 2 tunes from the local hard-disk to the ipod!!!

  • 25th May 2009 at 12:00 am

    I agree. This is THE worst piece of software EVER conceived of. For the amount of money that Apple makes off iPods, you would think that they could pay a REAL programmer. It would be SO much nicer if we could just copy and paste OUR music!!! The other day, I tired to "Restore this iPod" (mine). I started the restoration, and it barked out an error message about not being able to restore it, because the iPod is being used by another program. The ONLY program I had running was iTunes!!! The only way to restore the thing back to the original status is to use iTunes, but you can't restore it, because it can't figure out that iTunes is the only program using it! And has Apple NEVER heard of patches or updates? Let's waste time downloading the ENTIRE program every month, instead of just patching the slop we already have installed. That Zune is looking more and more better now, and I HATE Microsoft!!!

  • Starlight
    1st February 2009 at 12:00 am

    .. I totally agree, iTunes is the worst piece of software ever written. Its the poster child of annoying, intrusive, frustrating, inefficient, totally craptastic shiteful disaster. And I'm totally pissed that i *have* to use this piece of garbage, to put my songs on my ipod.

  • 17th January 2009 at 12:00 am

    I've been using Sharepod for the past few days with great success. Very clean interface, nothing fancy, but it does allow me to copy music between pc->ipod.

  • 13th January 2009 at 12:00 am

    I think itunes is the worst player ever ..it takes ages and then it is restricted and the worst part the think making it necessity for apple products they can make us fall in love with itunes and apple .. hell no ..i get even more irritated when i have to use itunes and got no options.. so apple should make itunes a lighter software or let other software sync with their products

  • 7th November 2008 at 12:00 am

    I feel your pain!!
    I use winamp as much as i can but certain aspects of the file coding cant be changed without itunes like audiobooks.


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