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The pain of transferring songs from iTunes to a Kindle Fire

Since the Kindle Fire uses the Android platform and all of my music is located on a Mac/iTunes using iTunes Match, I expected there to be a small challenge transferring songs to the Fire but I Google'd 'transferring songs to a Kindle Fire', found an overview of the process on Amazon and seemed like the steps would be fairly simple. However, the overall workflow was cumbersome and confusing.

I read the instructions and (after logging into Amazon) followed a link to the Amazon Cloud home.  I quickly noticed a clear call to action - an 'Upload Files' button in TWO locations on the screen and it was a well-organized screen (although it wasn't clear what Lists was, on the left side).  And uploading files seemed fairly intuitive and flexible by 1) control-clicking the file and choosing 'Upload to Cloud Drive', 2) dragging them to a Cloud Drive icon in the menu bar or 3) clicking the Upload Files button which invoked the native Mac folder window where I could select files or folders.  3 easy ways! 

Now I just had to upload those Shins and Katy Perry songs so my daughter could use them on her Fire.  I uploaded 24 songs and saw them on the Cloud Drive screen but…

I had uploaded 24 songs under the wrong amazon account (mine, not our other family account).  Now what?  I logged out of Amazon and logged back in under the correct account and discovered a message on the top left of the Cloud Drive screen that read 'Want to upload or download your music? Launch Cloud Player'.  I didn't notice this before since the two 'Upload Files' buttons caught my attention so fast.  I clicked it of course since all I wanted to do was upload music. Then something called the Amazon Music Importer, a totally different looking screen, opened in another tab - now I was confused.  Which way was I supposed to upload music? Using Cloud Drive or Music Importer (both Amazon products!)?

The Cloud Drive screen said I had 5GB of total storage (with no reference to music) available but the Music Importer screen (actually branded as Amazon Cloud Player) said I could only upload 250 songs, way less than 5GB.  And one was based on total storage and the other based on number of songs.  Later, I noticed the Cloud Drive screen actually did reference music (an Archived Music folder in the main table).  Amazon needs to present clear options to upload files to the cloud.  On the landing page for Amazon Cloud, they should state clearly that one product is meant for music and the other for non-music files. Apple does this pretty well in marketing iTunes Match.

I guess I'll go through the work to upload the songs now via Cloud Player since I have to upload those music files to the Fire but, even with all of iTunes Match's shortcomings (latency, missing artwork, review to come), I found Amazon's varying file upload products to be a confusing experience. Based on first impressions, the process of uploading songs is more intuitive and simply seems to 'just work' a bit better using iTunes than Amazon's Cloud product.


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