If getting an error below while doing an upload even though Device Manager is connected. 

You have to redo the setup. 

Go to Setup Tools > Setup Wizard > POS of Sale Devices > Devices Options > set the POS Device Manager back to None


Sign out in S5. Login again and get back to the window above. Choose Local then click Configure Point of Sale devices for this computer. 

There should be a green small pine tree will show up at the bottom right corner. Once done, sign out in S5 then login again. That pine tree will show up automatically and to show that is connected, check at the  bottom left corner Dev DPCS instead of Dev Off.

The port that is usually use is 5000. Open the green small pine tree at the bottom right corner. Under Data collector tab, you will put the port there.