The Truth About File Conversion (WMAs)

I was a long time user of Microsoft’s Zune.  My main reason for choosing it compared to the handful of main contenders in the world of MP3 players was that I was an exclusive PC user and I didn’t want anything to do with Mac.  Over the years, my household slowly converted to Mac and when I began using the iMac as my primary desktop, I knew it was only a matter of time before I would be switching my music collection over to iTunes.  Which then of course would mean getting an iPod.

Zune vs iPod

I hit my crossroads when I finally maxed out my 30GB Zune.  For a while I planned on upgrading to the 80GB Zune but after comparing the struggles I’ve had with Zune software compared to the ease of iTunes, going for the iPod was a no-brainer.  What makes Mac so appealing is how all its programs are  so compatible.  Everything is integrated.  Even as I write this blog entry, I’m also using my keyboard to make listening selections in my iTunes.

I received an early Father’s day present that cemented the fate of my music collection… the iPod Classic.  With 160GB, there is no estimate of maxing out my memory in sight, which gives me a peace of mind.  The only nightmare that resulted in this shift in music players was the dreaded issue of file conversion.  There were several instances where I forgot to switch the default file setting in my Zune software to MP3.  Therefore there was a considerable amount of my music collection in WMA (windows media audio).

Many of my know-it-all friends kept saying “oh just drag it to iTunes and it’ll convert the file for you.”  That sounded simple enough, however my attempts at such dragging proved unsuccessful.  Again, my know-it-all friends said “oh well, you must have something in your settings that’s preventing you from converting.”  Why would I change my settings to stop file conversion and why would the default setting of iTunes purposely make things difficult for me?  That just didn’t sound like Mac.  However I did see videos and other reports on the internet mentioning iTunes performing such miracles in the world of file conversion.  So why wasn’t my iTunes converting my WMAs?

I called a friend who was a former Mac Genius to try to get straight answers in the midst of this whole sorted mess.  Here is the truth about iTunes file conversion that countless related articles leave out. Only the PC version of iTunes will automatically convert WMAs into a readable format.  If you have a Mac, you either have to do that thing where you run windows on your Mac (kinda turning it into a PC), download iTunes, convert the file, then bring it over to your Mac profile, then drag it into your Mac iTunes.  However many users (myself included) don’t want to jeopardize their Mac by temporarily changing it to a PC just for the sake of a music collection.

To keep your Mac in its current setting and convert your WMA files leaves you with two main options:

1)  You can use a free website like Zamzar to convert a few files at a time, have the website e-mail a link to the converted files and then download them.

2)  Purchase/Download software to convert the files and then drag to iTunes.

Before I go into depth about both of these options, I want to make it clear that no matter which route you take in WMA file conversion for Mac, you WILL end up having to re-label (artist, album, genre, etc.) all of your songs once dragged into iTunes.

I tried the free route and used Zamzar at first.  You can upload 5 files at a time for conversion.  It will then take approximately 5 minutes to get an e-mail from the website, letting you know that the conversion was complete and give you the link to visit in order to download them.  I believe the link stays active for 24 hours.  After downloaded, you can drag your freshly converted files into iTunes and begin re-labeling them.  I would suggest this option if you have a small amount of files to convert.  The other benefit of using this option is that you can convert your WMA files to MP3s, which you will not be able to do in the next option.

Flip4Mac logo

Users with a large amount of files to convert may want to go with my second option and purchase/download software to convert the files faster.  I was recommended by my former Mac Genius friend to use Flip4Mac.  In doing so, it prompts you to download QuickTime Player.  You can actually download them for free and listen to your WMAs.  The only thing is, you have to purchase the pro version of QuickTime Player to export the file into another format.  After purchasing QuickTime Pro ($40) I was able to convert my WMA files to AIF, a readable format for iTunes.  NOTE:  QUICKTIME PLAYER WILL NOT CONVERT TO MP3. However, once I dragged the files over to iTunes and played them, I noticed that there was a demo sample played over all the converted files.  You’d hear 8 seconds of a song and then a voice say “you a listening to a file converted by…” which was horrible.  I’m glad I only converted one full album before discovering the demo message.  What happened was that I purchased the Pro version of QuickTime Player but I was still using the free version of Flip4Mac which supplied QuickTime Player.  In order to get rid of the demo message, I had to purchase the Pro version of Flip4Mac ($30).  Another important thing to remember is that QuickTime Player will not allow you to export the file until it is completely buffered.  I didn’t understand that at first and almost lost my mind.  Just be patient.

QuickTime Player logo

After spending $70 on software, I can successfully convert the 60+ albums worths of WMA files in my music collection to AIF files, acceptable for iTunes.  What I’m doing now is converting one album at a time so I can re-label them accordingly in iTunes.  The album art will pop up if the iTunes store can identify the album.  For me, I have a lot of indie/underground bands in my collection, which leaves me with the additional task of adding each cover image to the converted file folders.  Lastly, I dump the remaining WMA files in the trash to conserve memory space.  Not to worry, I still have everything backed up on a hard drives… even the original WMAs.

Besides my wallet, there were some other casualties in my music collection, and I’m not talking about the punk band.  When I had my Zune software, I also purchased a few albums without checking the option to download them in mp3 forms.  The albums were therefore downloaded in a WMA format that is DRM (digital rights management) protected, not allowing QuickTime player to even open the file.  In order to get any of these albums back into my collection, I need to open up the album in Zune software and burn it as an audio disc, then rip it to my iTunes.  Fortunately, I did rip a few audio discs for these DRM WMA file albums and was able to get them into my current collection in iTunes.  For the rest, they will have to remain on my external hard drive until I have access to a PC with a CD-ROM drive that is burn capable.

After all of this, do I still think this conversion was worth it?  Absolutely!  Zune software would do things on its own to my collection that I didn’t understand.  It would throw random songs into other albums, switch album covers with other artists that have nothing similar (song nor album names).  It would not sync properly with the Zune device, leaving 5 versions of the same album on my device, taking up more memory.  After a while, I had to just let Zune software do it’s own thing and leave my music collection in disarray.  I’m pretty anal about my music collection and iTunes lets me be as detailed oriented as I want and won’t mess with any changes that I make.


I’m sure that there are probably more affordable file conversion methods for you hackers out there but keep in mind, I’m an average computer user in my 30’s.  I didn’t have access to the internet til I was in college and so I’m not completely computer illeterate.  I grasp what I can and find the best answers and troubleshoot issues by googling them, as I assume most users do in my situation.  It’s the “Average Joe” for whom this post was written and if this post helps one user out there (even if it’s what NOT to do), then my time writing this was not wasted.


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