The Internet Chess Club (ICC) is a popular online chess server with more than 30,000 members worldwide including various celebrities and the best chess players in the world. Although the ICC Web site assures its users that the security protocol used between client and server provides sufficient security for sensitive information to be transmitted (such as credit card numbers), we show this is not true. In particular we show how a passive adversary can easily read all communications with a trivial amount of computation, and how an active adversary can gain virtually unlimited powers over an ICC user. We also show simple methods for defeating the timestamping mechanism used by ICC. For each problem we uncover, we suggest repairs and draw conclusions on how to best avoid repeating these types of problems in the future