After a player purchases a contract providing insurance against gambling losses, a server or other device in communication with a gaming device (e.g., a “player tracking” server, “slot accounting” server and/or other computer device) may operate to (i) receive game play data in association with one or more plays of the gaming device, (ii) determine a compliance status based on the received game play data and one or more play requirements associated with the contract, and (iii) provide a refund amount due to the player based on the compliance status. Before providing any refund, the server or other device may store a status indicator relating to the one or more plays indicating whether the play was compliant with the contract. Furthermore, an alert may be provided to the player if a particular play is not compliant with the contract.