SSLSmart - Smart SSL Cipher Enumeration

    Among other things, SSL Smart simply an advanced and highly flexible Ruby based smart SSL cipher enumeration tool. It is an open source, cross platform, free tool. It was programmed because a number of tools on the Windows platform allow users to test for supported SSL ciphers suites, but most only provide testers with a fixed set of cipher suites. Further testing is performed by initiating an SSL socket connection with one cipher suite at a time, an inefficient approach that leads to false positives and often does not provide a clear picture of the true vulnerability of the server. SSL Smart is designed to combat these shortcomings.

SSLSmart Features:

    SSL Smart offers a wide range of features to improve testing efficiency and reduce false positives. These features are as follows:

Content Scan (default):

    Exact server response can be seen in HTML and Text forms for each cipher suite selected for the test URL. Basically, it shows various server error messages received for weak cipher suites from live systems.


    Focuses only on success or failure of SSL socket connection with various cipher suites. This behavior does not offer any advantage over existing SSL testing tools and is thus likely to have similar issues with false positives. However, this scan is faster and consumes fewer network and CPU resources.

Dynamic Cipher Suite Support:

    Most SSL testing tools provide a fixed set of cipher suites. SSLSmart hooks into Ruby OpenSSL bindings and offers dynamic “on the fly” cipher suite generation capabilities.

Certificate Verification:

    SSLSmart performs server certificate verification. It uses the Firefox Root CA Certificate4 repository to perform Root CA verification. Additional Root CA Certificates can be added to the rootcerts.pem file or a custom .pem file can be supplied for Root CA Certificate verification.

Proxy Support:

    SSLSmart provides web proxy support. For results to be accurate, it is important to use a transparent proxy5.


    Reports can be generated in XML, HTML and Text formats along with their verbose versions. Verbose report versions include complete application response for each cipher suite and full details of the server certificate.


    Monkey patched Ruby API’s that form the backbone of SSLSmart can be consumed to write custom Ruby scripts for quick tests. These API’s can be consumed by users who work with the SSL Smart gem.
    What i liked the most about this tool is that SSLSmart supports XML, HTML, Text and their corresponding verbose reporting versions. In addition to details in the normal report, verbose versions include complete application responses for each cipher suite and full details of server certificates. Another feature that i liked is the API support. These API’s form the backbone for SSLSmart tests can be used to write custom scripts. SSLSmart gem includes source code and can be used by users who have Ruby installed on their systems and it comes from McAfee labs!

Platform Support and Installers:

    SSLSmart has been tested to work on the following platforms and versions of Ruby:
    Windows: Ruby 1.8.6 with wxruby6 (2.0.0) and builder7 (2.1.2).
    Linux: Ruby 1.8.7/1.9.1 with wxruby (2.0.0) and builder (2.1.2).

Download SSLSmart:

    SSLSmart 1.0 – –

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