RE: Application level pentesting

[<salexander () frontporch com>]

Sending random data over a network connection will only flush out the most obvious bugs.  Try sending data that is 
mostly correct but deformed in particular ways.  For instance, include trailing data on an otherwise valid 
request/command/etc or trim off a few bytes from an otherwise valid request, if there is an application-level header, 
set invalid options and lengths.  What you can do depends on the expected structure of the traffic.  Are there optional 
attributes that can be included?  What happens if you duplicate them?  If the application uses multi-stage transactions 
(such as DHCP with discover/offer/request/acknowledge/release vs DNS with request/reply), try fudging data at different 
stages of the transaction.

Does the program store encryption keys in memory longer than needed?  This is easier to find in a code review than 
during testing but you may be able to find out using a debugger and a known key.

What is exposed to an attacker (open network ports, registry, files, etc)?  What can the attacker control?

I hope this helps,

Steven  


-----Original Message-----
From: intel96 [mailto:intel96 () bellsouth net]
Sent: Fri 6/30/2006 9:42 AM
To: pen-test () securityfocus com
Subject: Application level pentesting
 
To all,

I am pentesting an application that is written in several languages but
is complied into a single application.  So looking at the application
with FxCop or Reflector for .NET apps does not work.

The application draws an image on the screen that cannot be moved.  The
image has two values username and password.  The application only
accepts mouse entries on a virtual keyboard, which rotates every 60
seconds.  The application form fields which are masked with "*" cannot
be read with applications like Foundstone's Showin.   Microsoft Spy++
does cannot see the values in the form fields once they are entered. 

The application writes nothing to the registry that can be used.  

The application uses the following items when running:

1.  InternetFortezzaCard - part of WININET.dll
2. InternetInitializedAutoProxyDll - part of WININET.dll
3.  MSWSOCK.dll
4.  USER32.dll
5.  Kernel32.dll

Sending random data to the open UDP (Foundstone UDPflood) and TCP
(Foundstone Blast) ports does not crash the application. 

Cramming random data into the username field does nothing.

Does anyone have any recommendations on how to pentest the application
deeper?

Thanks,

Intel96

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This List Sponsored by: Cenzic

Concerned about Web Application Security?
Why not go with the #1 solution - Cenzic, the only one to win the Analyst's
Choice Award from eWeek. As attacks through web applications continue to rise,
you need to proactively protect your applications from hackers. Cenzic has the
most comprehensive solutions to meet your application security penetration
testing and vulnerability management needs. You have an option to go with a
managed service (Cenzic ClickToSecure) or an enterprise software
(Cenzic Hailstorm). Download FREE whitepaper on how a managed service can
help you: http://www.cenzic.com/news_events/wpappsec.php
And, now for a limited time we can do a FREE audit for you to confirm your
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