If the BOL is not auto printing check the setting under Edit>>Setup
Make sure the setting Auto Print BOL is checked
If this is correct also make sure your PPS Print Server Software is running.
Go to Edit >> UserData >> Production >> Operators. Make sure the BOL Printer is selected properly
The printer listed here is a printer on the machine where the PPS Print Server resides since it is the app that actually does the printing.
If you are emailing BOL's make sure there is a valid email under BOL Email on the customer edit screen