Songs won't start playing sometimes.

[DJ Nativus]

I am using Subsonic with Mac OS 10.11 and having issues in multiple web browsers with using the 320 kbps MP3 streamer. Randomly when starting a new song, it will just not play. It's not paused it's just not starting. Sometimes if I skip a few seconds into the song, it will start.

I have approximately 3TB of music (mostly FLAC) on a Raidz (ZFS) array. I should note using Jukebox mode at home doesn't have this issue at all. It's only when using the streamer player through a web browser when away from home. I have 300 mbps down and 15 mbps up so I don't think this is a bandwidth issue.

I've searched and haven't found much help. Any troubleshooting steps would be great.