Trouble playing files off HDD

So I have a RPi3 running OSMC and I have a 4TB HDD connected to the Pi. I have an SMB share setup so that I can see the files on the HDD on my laptop. I usually use my iPhone Kodi remote to control OSMC but sometimes I use the web browser on my laptop using the Chorus 2 interface.

Now, I can use the Chorus 2 interface to play files on Kodi, but if I hit the local tab in the top right so that say I want to listen to my music through headphones on my laptop, nothing happens. It shows the little file playing icon, but the time doesn’t move forward and no sound ever comes out. I’m really curious why this feature no longer is working for me, when I’ve had it work no problems at all in the past.

Well first start of investigation would be debug enabled logs
Please see How to submit a useful support request - General - OSMC

Secondly, did you try different browser?

Lastly if the debug logs doesn’t bring us closer to a solution next step would be to review network traffic with tcpdump