Automated Scanning with Arachni

Scanners have a tricky reputation. Their point-and-click simplicity and utility as automated reconnassiance tools means they get love from script kiddies and professionals alike. They also have compelling use cases for flushing out certain vulnerabilities, like XSS, where there may be too many input vectors or payload varities to feasibly go through the application by hand. The problem is a lot of the most popular scanners, like Burp Suite and Websecurify, rely on a GUI for their targeting information and follow a similar pattern:
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Pentest Proving Grounds

One of the most helpful tools in learning the fundamentals of penetration testing is the ability to test your analysis against deliberately-vulnerable applications - sites and/or apps with consciously introduced flaws, catalogued for easy reference. Beyond a great introductory exercise, testing against deliberately vulnerable apps can also be a great way to calibrate new scanners or automated reconnaisance methods. And in addition to the actual vulnerable endpoints within the applications themselves, many of them also feature their own guided tutorials explaining how to detect - and often mitigate - the vulnerabilities they contain.
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