Hey, just so you know ... this post is now about 7 years and 9 months old. Please keep that in mind as it very well may contain broken links and/or outdated information.

Now that I have an Amazon Echo in the house, I wanted to be able to play my music collection by just asking Alexa to do it. Since the Echo relies on the cloud, it can only play local music when it’s paired to a device as a speaker. So I could pair my iPhone or PC to it and play music from iTunes, but that’s so … manual! In order to say “Alexa, play some Oingo Boingo” and have her look at my own tracks instead of what’s available for free on Prime Music, those music files needed to be in Amazon’s cloud so I decided to try Amazon Music.

Prime subscribers can upload up to 250 tracks to their Amazon Music library for free, but I have about 20x that many songs so I paid the $24.99 for a year of the service, which increases the limit to 250,000 songs (a lot more than I have). This is in line with what Apple charges for iTunes Match but Google Music (which I’ve been using as just another cloud backup for my music library) is free up to 50,000 tracks. The Echo doesn’t work with Google Music though, obviously, as Amazon wants to keep you in their ecosystem, so I paid for the subscription, downloaded the app, and started uploading my library.

I dislike iTunes, but I’ve learned to live with it as a necessary evil that comes with owning an iPhone. I’ve spent a lot of time over the years perfecting and correcting the ID3 tags in my MP3 files and have my library just right and the way I like seeing it. The upload to Amazon Music really screwed with all of that. Like iTunes Match, Amazon examines the file as it’s being uploaded and tries to determine if it already exists in their own extensive library. If it finds a match, it doesn’t bother uploading your file and instead “links” the track in Amazon Music to your own library. This saves on time and space, but the matches aren’t always correct. It may match the track, but on a different album (say, on a compilation instead of the original), which is annoying. And for the tracks it can’t match, it uploaded fine, but then seemed to not always be able to process the metadata correctly. So I had tracks with the correct album and artist, but the title would be filename.mp3. You would think doing a search on “.mp3” would find all the tracks with this problem, but it didn’t so I had to scroll through my entire library looking for these incorrect track names so I could manually correct them. A lot of those unmatched tracks also uploaded with “Unknown Artist” when it could have just looked at the ID3 tags to get this information. I also had a lot of problems with duplicates. At one point during the upload, the app crashed so I had to restart it. The app (or the cloud service) is supposed to be able to detect duplicates but I ended up with a lot of duplicate tracks I had to manually clear out. Overall, the initial process of getting my music library into Amazon Music was frustrating and time consuming. Hopefully this was just a one-time conversion hassle and not something I’ll have to deal with a lot going forward.

Another huge oversight on Amazon’s part is the inability of the app to import iTunes playlists. Google Music had no problem with importing my iTunes playlists that I’ve sent a lot of time curating but the only way to get those into Amazon Music is to manually re-create them! 😮 And doing this in the desktop app (or on the web) is painful in a way I cannot describe. Search for a track, wait for results, click it, then add it to a playlist, select the playlist, click OK, repeat, repeat, repeat for hundreds of songs. The iOS app makes it look like you can import your iTunes playlists but that only works if you have the music downloaded from the cloud to the Amazon app on your phone. Very confusing. There’s also a 500 song limit for cloud playlists, but I can overlook that since my 938 song playlist of 80s music would take me 2.7 days to listen to, according to iTunes.

The desktop app is also very confusing and the user interface leaves a lot to be desired. My biggest problem with it is the split between your local music and your cloud music. In my case, both libraries are the same (since I’ve uploaded everything). When you do a search, you can’t limit the search results by location so you’ll see the same track twice (the local copy and the cloud one) but there’s no indication of which one is which. You just have to pick one, and then look at the upper left hand corner to see if the “cloud” or “PC” icon is lit. I did all of my metadata corrections on the cloud side, which means the local library still has the old, incorrect data. If I were to upload the tracks again, it would overwrite all of my work with the original, bad data the app imported from iTunes. The desktop app is also very sluggish and after you make a change to a cloud file, the whole window may go blank and blink while it uploads your changes. If you were trying to scroll or do something when it does this, you have to start all over. This app made me physically angry while I was using it, it’s just terrible!

All that angst aside, I can now say “Alexa, play my Raid the Arcade” playlist and my music will come out of the Echo’s speaker. Pretty cool, I just hope it was worth the time and effort and $25. 😉