If I were only given a single tool for a web application penetration test, that would definitely be a web interception proxy!
As you can check within Samurai WTF, the number of web interception proxies available to web app analyst and pen-testers is... (at least) quite large. During the last years (after the old initial Achilles days... Wow!, from Oct 13, 2000), a few proxies have become the web application security assessment tool of choice. OWASP Webscarab, together with Paros (Proxy), have been two of the most commonly used open-source alternatives, with Burp (Suite) on the free/commercial side (but not open-source).
Unfortunately (or not... keep reading ;-p) Webscarab and Paros were somehow discontinued. The lastest official Webscarab build (not from GIT) is from May 2007, and Webscarab-NG (Next Generation) was born as a very promising Webscarab replacement, but is slowly progressing with new features and releases. Paros ended up on the famous 3.2.13 version from August 2006 (5 years ago!) and a replacement project or fork was born afterwards, called Andiparos. In parallel, a new OWASP project saw the light, called ZAP (Zed Attack Proxy). On a very smart decision from their leaders (Psiinon and Axel), both projects joined forces to contribute to a single and common open-source web interception proxy (and security assessment tool, considering all the features currently available within ZAP), keeping the name of ZAP for the final project. Therefore, OWASP ZAP (Zed Attack Proxy) is definitely the current open-source web interception proxy and security assessment tool of reference.
What all these web interception proxy tools have in common? They have been developed in Java, what makes them great multi-platform (Windows, Linux, Mac OS X...) security assessment tools.
Experience has demonstrated during the last few years that pen-testers need to use two types of tools on their daily activities: the latest official stable tool release, typically distributed by the project as a prepackaged and ready to install bundle (.tar.gz, .zip, .jar, etc), and the most current development tool revision, the one that includes the most cutting edge, neat and mighty features, options, and capabilities, typically distributed by the project from the official Subversion (SVN/CVS, GIT, etc) repository.
Most pen-testing tools are developed using traditional languages, like C/C++ (e.g. nmap), where the standard 3-way build handshake works like a charm ("./configure", "make" & "sudo make install"), or using interpreted languages, where there is no need to build the package, such as Ruby (e.g. Metasploit), Python (e.g. w3af), or others.
But... what about the Java-based web interception proxies? I've discovered that there is a significant barrier to entry that make it difficult for pen-testers to enter into the building process of this kind of tools, as a simple "javac" (Java compiler) invocation does not make the trick. In order to compile and build Java-based web interception proxy tools, as they make an extensive use of GUIs and library sets, a Java IDE (Integrated Development Environment) is required.
As a result, lots of security professionals cannot and are not using the most current features of these tools until a new official version is released by the project. In order to overcome this, I have released the "Building OWASP ZAP Using Eclipse IDE for Java… Pen-Testers" guide, available for download (as usual) from Taddong's lab.
The goal of this document is to provide a simplified step-by-step guide web app pen-testers can go through to be able to easily build the most current OWASP ZAP version from the official Subversion repository by using the open-source Eclipse Java IDE. A final appendix provides some brief guidance for those interested on, not only using the latest tool features, but contributing to the OWASP ZAP project (what I encourage you to do).
Do not forget to always, but specially when using the most current development version, extensively test the tools on your lab environment before using them against the real pen-test targets, probably in production (at least, before you started using the tool... :-)