I'm totally new in the field of penetration testing, like almost no experience, only read lots of books and papers. I encountered lots of interesting tools during studying, many are famous like Metasploit, Nmap, OpenVas... etc. and other tools that aren't known or less famous, along with lots of code on websites like Github.

My objective is: Building a tool that can automate pen testing using Python. It should be able to connect some tools together like some already done projects.

My problem is: I need to select a set of tools to be used, but since I have low experience in the field, I don't know how to evaluate these tools.

What I need: The last thing I need is a list of tools. I'm welling to know if there are some right steps or a framework to evaluate these tools. If not, then how can I say that this tool is better than that or this tool is more convenient... etc. As a pen tester or a security expert: How do you evaluate and choose these tools during your work?

Just to let you know, I use Backtrack and aware of some valuable tools on it.

Please before thinking about closing my question or down voting it, try to help me. I'm kinda confused and really need help with this issue. If you found my way of thinking wrong too you're welcomed to correct it.

Edit: This tool is being built for a college project.

closed as not constructive by Lucas Kauffman, Mark Davidson, Ayrx, AJ Henderson, user2213 Mar 13 '13 at 13:57

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As a pentester automation makes up about 1% of what I do and is only useful because it can catch low hanging fruit. Firing off Nessus or some webapp scanner takes less than an hour. The remaining time is spent actually hacking the application. I look the source code for security critical components, and fuzz strange API's with burp. Be observant, attention to detail. A finding start as simple as a strange error message, a "Huh, that is funny" moment.

The tools I commonly use are (no specific order):

The scientific method
a decompiler
a debugger

In any case I suggest getting some findings under your belt before your start writing hacking tools. There are already some great tools out there.

  • Thank you Rook. The tool I wished to build is actually for a project at college, you're right about the automation not being so important during a pen test. I'm also working on increasing my hacking abilities so your advice is valuable. – Dee Taha Mar 11 '13 at 16:54

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