Currently in order to send EDI Messages to a Customer they must have an Integration and it must be set to send return messages. By default return messages will only be generated and sent if the bookings are created via EDI. 

However if a booking is created manually no EDI messages will be sent. 

To force FreightTracker to send EDI messages back regardless of booking creation type (EDI or manually created) the customer record must be edited. 

Turn on the EDI Option. This will cause EDI messages to sent to the customer regardless of whether the Booking was imported via EDI or was manually created.