SEC595: Applied Data Science and AI/Machine Learning for Cybersecurity Professionals

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Contact UsTCP/IP protocols have long been subject to man-in-the-middle (MITM) attacks, but the advent of SSL/TLS was supposed to mitigate that risk for web transactions by providing endpoint authentication and encryption. The advent of Dug Song's 'webmitm' in late 2000 demonstrated the feasibility of mounting an MITM attack on the protocol, but a properlyconfigured client SSL implementation would warn the user about problems with the server certificate. This paper examines the mechanics of the SSL protocol attack, then focuses on the greater risk of SSL attacks when the client is not properly implemented or configured. One faulty SSL client implementation, Microsoft's Internet Explorer, allows for transparent SSL MITM attacks when the attacker has any CA-signed certificate. An even greater risk is posed by unprotected systems where an attacker can preload his/her own trusted root authority certificates. In public environments such as libraries and computer labs, there is little to prevent such an attack from taking place. Casual observation of such places indicates that an attacker would see them as low-risk, high-opportunity.