Messaging News

February 2011

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are critical Internet infrastructure. Most consumer Web, email, and VoIP traffic relies on SSL for security as does sub- stantial portions of enterprise Internet traffic both from SSL enabled Web applications and SSL-based VPNs. T Fundamental problems increasingly put this infrastructure at risk. Significant risks include flawed implementations of the SSL protocol and PKI, inadequate verification mechanisms for certificate issuance, limited implementation of revocation mechanisms, and involvement by state actors in the issuance process. There are no viable alternatives to the mainstream use of SSL that are currently widely accepted or deployed. Major Problems Areas For SSL Cryptographic Flaws The first analyses of problems with the protocol focused on the cryptographic aspects of the implementations, which he security of the transactions for much of the con- sumer Internet relies on the Secure Socket Layer (SSL) protocol. SSL and its Public Key Infrastructure (PKI) ON MESSAGE WITH BEN GROSS SSL is Critical Infrastructure at Risk largely stabilized with the release of TLS 1.0/SSL 3.1 in 1999. The IETF (Internet Engineering Task Force) released the last version of SSL in 1996, which it superseded with the Transport Layer Security (TLS) protocol released in 1999. Still the protocol is primarily referenced as SSL. TLS versions 1.1 and 1.2 added further security refinements, although they are not yet widely implemented or deployed. Recent flaws target weakness in the SSL framework and not the encryption itself. One notable exception is the 2008 discovery of weakness in the MD5 cryptographic hash function that allowed security researchers to create a false Certificate Authority certificate that could sign other valid SSL certificates. User Interface Problems The second phase focused on user interface and user experience aspects of SSL. In particular, people simply ignored the large number of security warnings about SSL certificate problems no matter what their severity. Users are more vulnerable to both hijacking and phishing attacks when they become desensitized to certificate warnings. The Mozilla Foundation investigated usability problems and experimented with multiple user interfaces to prevent and train users from navigating to sites with invalid SSL certificates. Implementation Flaws The OpenSSL toolkit is widely used to generate crypto- graphic keys for SSL certificates and SSH keys. In 2006, a developer on the Debian Linux distribution team modified the OpenSSL source to eliminate errors generated by a de- bugging tool. The change had an unintended side effect that eliminated most of the entropy destined to seed the pseudo- random number generator, which caused the modified ver- sion of OpenSSL to produce weak cryptographic keys for the Debian version of OpenSSL. Another Debian developer discovered the flaw in 2008. In the intervening time, flawed versions of OpenSSL created an estimated 25,000 weak and easily compromised SSL keys. In 2009, researchers discovered the potential for man-in- the-middle type attacks by targeting the renegotiation feature of SSL, which allowed changes to keys in-connection to accomplish tasks such as upgrading the key strength. I described the problem in A Practical Attack and Fixes for Current SSL/TLS Vulnerabilities. 12 MESSAGING NEWS FEBRUARY 2011

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