Can the system automatically charge late fees?

Sure! Select a student and go to Transactions in the left menu.

Select the Debit posting type (1) and enter the amount you are charging.

Then click the Due Date link (2).

Select a due date by either clicking the calendar icon and picking a date or by using the Quick Links (3).

Then select your late fee policy (4), which tells the system how to calculate the late fee if this charge is not paid by the due date.

Post Transaction (5).