Uploading music files to Google Play Music keeps stalling on Mac OS X

With Google Play, I can now upload my entire music library into the cloud (I only have about 9000 songs) and access it anywhere in the world! Unfortunately, you have to get your songs into the cloud to begin with.

In theory, this should be easy– Google Music has a Chrome extension that is supposed to keep your iTunes library in sync with with your Google account. However, when I tried it (Mac OS X Yosemite 10.10.5, Chrome Version 47.0.2526.106 64-bit), it would keep stalling/crashing. I’m not the only one with the problem– lots of others have it as well: https://productforums.google.com/forum/#!topic/play/2I6w7em3Eb4

To fix this, I disabled the Chrome extension and downloaded the Mac OS X native Music Manager and directed it to sync iTunes. That worked for a while, but then it started to crash as well– not as often, but still frustrating.

Looking at the logs (~/Library/Logs/MusicManager/MusicManagerHelper.log), there were no obvious errors, but it did suspiciously seem to crash while trying to parse certain .ipa files. These are the iOS application files that are contained, for legacy reasons, in ~/Music/iTunes/iTunes Music/Mobile Applications.

In any case, I suspect I could fix this by manually just adding all .mp3 files (thus skipping the .ipa files), but I decided to just hack through it by creating an Apple launchd job that auto-restarts Music Manager every minute if it isn’t already running. This seems to solve the problem.

To do this, open up Terminal and create the following file– fine to put it in your home directory. Name it com.google.musicmanager.plist

<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple Computer//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
	<dict>
		<key>Label</key>
		<string>com.google.musicmanager</string>
		<key>ProgramArguments</key>
		<array>
			<string>/Applications/MusicManager.app/Contents/MacOS/MusicManager</string>
		</array>
		<key>StartInterval</key>
		<integer>60</integer>
	</dict>
</plist>

Save it, and then run:

launchctl load com.google.musicmanager.plist

It should start running within a minute– you’ll see a headphone icon in the upper right corner of your screen.

When all of your music is finished uploading, just type the following to unload the launchd job:

launchctl unload com.google.musicmanager.plist