winAUTOPWN has been an old favourite to automate windows hacking and vulnerability testing. The project is the brainchild of Azim Poonawala of [C4]Closed Circuit Corporate Clandestine and saw its first release in 2009. Fast forward to 4 years; it has matured into a good exploitation framework with a plethora of options. As the Author states about it -
Autohack your targets - even if you have consumed and holding a bottle of 'ABSOLUT' in one hand and absolute ease (winAUTOPWN) in the other.
In layman terms, winAUTOPWN is a unique exploit framework which helps in gaining shell access and pwning (aka exploiting vulnerabilities) to conduct Remote Command Execution, Remote File/Shell Upload, Remote File Inclusion and other Web-Application attacks. To add cherry on the top, it can also help in conducting multiple types of Denial of Service attacks on targets, furthermore, It can also be used to test effectiveness of IDS/IPS and other monitoring sensors/softwares.
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