Payment gateways are a high value target as they store financial and private information. Despite the requirements placed on payment gateways by credit card companies and local government privacy regulations, most payment gateways suffer from security vulnerabilities. This presentation explores vulnerabilities found in payment gateways during penetration testing as well as new attacks with minimal focus on client side exploitation. Some examples of the vulnerabilities discussed within the presentation are the ability to man in the middle transactions, perform fraudulent transactions, attacks against "tamper proofing" of transactions and old fashioned web vulnerabilities in payment gateway applications or shopping carts.