The use of TLS by malware poses new challenges to network threat detection because traditional pattern-matching techniques can no longer be applied to its messages. However, TLS also introduces a complex set of observable data features that allow many inferences to be made about both the client and the server. We show that these features can be used to detect and understand malware communication, while at the same time preserving the privacy of benign uses of encryption. These data features also allow for accurate malware family attribution of network communication, even when restricted to a single, encrypted flow. To demonstrate this, we performed a detailed study of how TLS is used by malware and enterprise applications. We provide a general analysis on millions of TLS encrypted flows, and a targeted study on 18 malware families composed of thousands of unique malware samples and ten-of-thousands of malicious TLS flows. Importantly, we identify and accommodate the bias introduced by the use of a malware sandbox. The performance of a malware classifier is correlated with a malware family's use of TLS, i.e., malware families that actively evolve their use of cryptography are more difficult to classify. We conclude that malware's usage of TLS is distinct from benign usage in an enterprise setting, and that these differences can be effectively used in rules and machine learning classifiers.
The majority of electronic communication today happens either via email or chat. Thanks to the use of standardised protocols electronic mail (SMTP, IMAP, POP3) and instant chat (XMPP, IRC) servers can be deployed in a decentralised but interoperable fashion. These protocols can be secured by providing encryption with the use of TLS---directly or via the STARTTLS extension---and leverage X.509 PKIs or ad hoc methods to authenticate communication peers. However, many combination of these mechanisms lead to insecure deployments. We present the largest study to date that investigates the security of the email and chat infrastructures. We used active Internet-wide scans to determine the amount of secure service deployments, and passive monitoring to investigate if user agents actually use this opportunity to secure their communications. We addressed both the client-to-server interactions as well as server-to-server forwarding mechanisms that these protocols offer, and the use of encryption and authentication methods in the process. Our findings shed light on an insofar unexplored area of the Internet. The truly frightening result is that most of our communication is poorly secured in transit. Transport Layer Security is the standard, widely deployed protocol for securing client-server communications over the Internet. TLS is designed to prevent eavesdropping, tampering, and message forgery for client-server applications. Here, the author looks at the collection of standards that make up TLS, including its history, protocol, and future.