For further troubleshooting, can you send us a copy of your LightSpeed Server's logs.
Here are instructions how to do this:
Navigate to Macintosh HD/Library/Application Support/LightSpeed Server/.
Right-click or Control-click on the logs folder and select 'Compress "logs"'. This will save a logs.zip file on your Desktop.
Attach this zip file in your email to us or, if it's too big to send via email, login to our help desk system and attach it to your ticket.