The Secure Socket Layer (SSL) and Transport Layer Security (TLS) are the most widely deployed security protocols used in systems required to secure information such as online banking. In this paper, we propose three handshakeinformation- based methods for classifying SSL/TLS servers in terms of security: (1) Distinguished Names-based, (2) protocol version and encryption algorithm-based, and (3) combined vulnerability score-based methods. We also classified real-world SSL/TLS servers, active during July 2010 to May 2011, using the proposed methods. Finally, we propose 45 features, deemed relevant to security assessment, for future SSL/TLS data collection. The classification results showed that servers had bimodal distribution, with mostly good and bad levels of security. The results also showed that the majority of the SSL/TLS servers had seemingly risky certificates, and used both risky protocol versions and encryption algorithms