Identifying HTTPS configuration and issues

Any website or web application that manages any kind of sensitive or personally identifiable information (names, phone numbers, addresses, health; credit; or tax records, credit card and bank account information, and so on) needs to implement a mechanism to protect the information on its way from client to server and vice versa.

HTTP was born as a cleartext protocol. As such, it doesn't include mechanisms to protect the information exchanged by the client and server from being viewed and/or modified by a third party that manages to intercept it. As a workaround to this problem, an encrypted communication channel is created between the client and server, and HTTP packets are sent through it. HTTPS is the implementation of the HTTP protocol over a secure communication channel. It was originally implemented over Secure Sockets Layer (SSL). SSL was deprecated in 2014 and replaced by Transport Layer Security (TLS), although there are still many sites that support SSLv3, be it for misconfiguration or for backwards compatibility.

Supporting older encryption algorithms has a major drawback. Most older cipher suites are found to be easily breakable by cryptanalysts, within a reasonable amount of time using the computing power that is available today.

A dedicated attacker can rent cheap computing power from a cloud service provider and use it to break older ciphers and gain access to the cleartext information. Thus, using older ciphers provides a false sense of security and should be disabled. The client and the server should only be allowed to negotiate a cipher that is considered secure and is very difficult to break in practice.

Kali Linux includes a number of tools that allow penetration testers to identify such misconfigurations in SSL/TLS implementation. In this section, we will review the most popular ones.

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