WebGoat

WebGoat is a deliberately insecure J2EE web application maintained by OWASP designed to teach web application security lessons. In each lesson, users must demonstrate their understanding of a security issue by exploiting a real vulnerability in the WebGoat application. For example, in one of the lessons the user must use SQL injection to steal fake credit card numbers. The application is a realistic teaching environment, providing users with hints and code to further explain the lesson.

Dradis

dradis is an open source framework to enable effective sharing of information among participants in a penetration test. It is a self-contained web application that provides a centralised repository of information to keep track of what has been done so far, and what is still ahead.

BeEF

BeEF is a browser exploitation framework. This tool will demonstrate the collecting of zombie browsers and browser vulnerabilities in real-time. It provides a command and control interface which facilitates the targeting of individual or groups of zombie browsers. It is designed to make the creation of new exploit modules easy.

Netsparker

Netsparker is a web application security scanner, with support for both detection and exploitation of vulnerabilities. It aims to be false positive–free by only reporting confirmed vulnerabilities after successfully exploiting or otherwise testing them.

Social Engineer Toolkit

The Social Engineer Toolkit incorporates many useful social-engineering attacks all in one interface. The main purpose of SET is to automate and improve on many of the social-engineering attacks out there. It can automatically generate exploit-hiding web pages or email messages, and can use Metasploit payloads to, for example, connect back with a shell once the page is opened.

Canvas

Canvas is a commercial vulnerability exploitation tool from Dave Aitel's ImmunitySec. It includes more than 370 exploits and is less expensive than Core Impact or the commercial versions of Metasploit. It comes with full source code, and occasionally even includes zero-day exploits.

Core Impact

Core Impact isn't cheap (be prepared to spend at least $30,000), but it is widely considered to be the most powerful exploitation tool available. It sports a large, regularly updated database of professional exploits, and can do neat tricks like exploiting one machine and then establishing an encrypted tunnel through that machine to reach and exploit other boxes. Other good options include Metasploit and Canvas.

w3af

W3af is an extremely popular, powerful, and flexible framework for finding and exploiting web application vulnerabilities. It is easy to use and extend and features dozens of web assessment and exploitation plugins. In some ways it is like a web-focused Metasploit.

Metasploit

Metasploit is a perfect open-source platform for developing, testing, and using exploit code. The extensible model through which payloads, encoders, no-op generators, and exploits can be integrated has made it possible to use the Metasploit Framework as an outlet for cutting-edge exploitation research. It ships with hundreds of exploits, as you can see in their list of modules. This makes writing your own exploits easier, and it certainly beats scouring the darkest corners of the Internet for illicit shellcode of dubious quality. One free extra is Metasploitable, an intentionally insecure Linux virtual machine you can use for testing Metasploit and other exploitation tools without hitting live servers.