: There are several applications designed specifically for this:
: 
: Mutillidae
: 
http://www.irongeek.com/i.php?page=security/mutillidae-deliberately-vulnerable-php-owasp-top-10
: 
: Foundstone's Hacme Bank and Hacme Travel
: http://www.foundstone.com/us/resources-free-tools.asp
: 
: WebGoat
: http://www.owasp.org/index.php/Category:OWASP_WebGoat_Project 
: 
: 
: I believe there are more, but those are the first to come to mind.

A couple more:

Stanford SecuriBench
http://suif.stanford.edu/~livshits/securibench/

w3af's "moth"
http://sourceforge.net/project/showfiles.php?group_id=170274
http://sourceforge.net/mailarchive/forum.php?thread_name=cdfaf8b20905051759o76a0f6f1o171928dd9b1d5e30%40mail.gmail.com&forum_name=w3af-develop


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