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How to Fail A Penetration Test Concepts in Securing a Network. Scott Teeters, Jr. MicroSolved, Inc. in partnership with Sogeti USA . Background . Sogeti USA Sogeti USA LLC, part of the Sogeti Group, provides information technology services to businesses and public sector organizations.

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How to Fail A Penetration Test

Concepts in Securing a Network

Scott Teeters, Jr.

MicroSolved, Inc.

in partnership with

Sogeti USA

  • Sogeti USA
    • Sogeti USA LLC, part of the Sogeti Group, provides information technology services to businesses and public sector organizations.
  • MicroSolved,Inc.
    • MicroSolved, Inc. provides information security services and consulting to Sogeti USA customers.

today s agenda
Today’s Agenda
  • Common issues that cause an organization to fail penetration tests
  • Some suggestions on how an organization may improve their security posture


All ideas mentioned in this presentation also apply to any wireless or modem (dialup) systems as well.

policy issues
>Policy Issues

problems with policies and processes
Problems with Policies and Processes
  • Inconsistent application of policies throughout the organization
  • Poorly designed policies and standards
  • Example: Password are not required for all forms of network and application access

proper use of policies and processes
Proper Use Of Policies and Processes
  • Policies and Processes are developed in accordance with industry standard best practices, and/or an appropriate regulatory guideline
  • Policies are broad enough to establish the expected behavior in the user population
  • Policies are consistently applied across the organization

  • A proper password policy
    • Passwords are required for all forms of network and application access
    • Password strength is mandated to meet a specific level (IE: 7 Chars, Alpha-Num, w/special characters and mixed case)
    • Password rotation is large enough to prevent password reuse issues
    • Administrative/root access is strongly protected, requiring a token

another policy issue
Another Policy Issue:
  • Poor Domain Trust Choices

Who trusts who?

    • Weak trust structure
      • Types of trust
      • Some domains have less security than others

  • Good Domain Trust Choices

Who trusts who?

    • Unidirectional trust
      • Allows work to be done
      • Protects Production domain

process issues
Process Issues:
  • Information Leakage Problems

Who’s saying what?

    • Example of Usenet leakage

"Gary Smith" wrote in message news:#[email protected]

I have a data communication application that uses TAPI 2.x for doing async modem protocols. This application has been in use for three years. I have discovered a problem, and can recreate it where data is lost somewhere between the modem and my application but it only happens on Windows 2000 machines. If I run it on a Windows NT 4.0 machine, it works fine...

process solution
Process Solution:
  • Combating Information Leakage

Who’s saying what?

      • Have technical staff members use email and Usenet posting addresses not associated with the organization
      • Make sure users know not to post corporate identifiers online
      • Monitor the Internet for information leakage problems and address them ASAP

problems with patching
>Problems with Patching

poor patch management
Poor Patch Management
  • Systems are not current on patches/hotfixes
  • Patches are not consistently applied throughout the organization
  • Patches are more than security, they also may provide:
    • Stability
    • New Features
    • New Ways to Prevent Illicit Access
  • Patch problems can hurt you!

patching details matter
Patching Details Matter
  • Sometimes, patches have to be applied in a specific order or manner
    • Failing to do so, may actually INCREASE your vulnerability!

proper patch management
Proper Patch Management
  • Patch levels are monitored on a regular basis using manual processes or automated vulnerability assessments
  • Patches are tested in a isolated environment before being applied to production systems and devices
  • Patches apply to operating systems, applications and even hardware devices
  • Policies and standards clearly define the mechanisms and frameworks for acquiring, testing and deploying patches, fixes and version upgrades

configuration downfalls
>Configuration Downfalls

configuration issues
Configuration Issues
  • Poorly configured perimeter implementations
    • Example: Firewall rules are not granular or allow too much access
  • Internal network does not meet industry standard best practices
    • Example: Unnecessary services offer footholds for attackers
  • Systems are not adequately hardened
    • Example: Access controls allow easy access to confidential data

proper perimeters
Proper Perimeters
  • Access controls systems (ie: firewalls, router, etc.) start with a deny all attitude
  • Services are added with specific granularity as required for business
  • Internet visible systems are physically and logically segregated from production networks
  • Intrusion detection tools allow for easy anomaly and danger identification
  • Systems are carefully monitored via log files or agents using a manual or automated process
  • Alternate forms of access (ie: remote management, VPN, RAS, etc.) terminate in a DMZ or segregated segment

proper network configuration
Proper Network Configuration
  • Domain trusts are properly applied and implemented
  • Unneeded services are not running on network connected systems and devices
  • Proper egress controls assist in preventing malware spreading and attacks against other networks
  • IDS is deployed to assist with problem detection and troubleshooting
  • The network is monitored for changes in performance and traffic levels which could indicate a security or other type of issue

proper system configuration
Proper System Configuration
  • Systems are hardened in accordance with a baseline
    • Examples: SANS configurations, CIS baselines
  • Systems are up to date on patches and fixes
  • Unneeded services have been disabled
  • All systems use anti-virus software with regular automatic updates
  • Personal firewalls are deployed where appropriate, at a minimum on all laptops and notebooks
  • Access controls have been appropriately applied to each device and its file system
  • Users are aware of existing policies and guidelines

keeping it all together
Keeping it All Together
  • You have a complex environment
  • Not all users will behave as expected
  • Patches and fixes come fast and furious
  • How do you keep all these variables under control?


how to fail a penetration test
Implement poor policies and processes

No policies and processes also count!

Mismanage patches and fixes

Misconfigure your perimeter, network and/or systems

Take a number, attackers will be right with you…

How To Fail A Penetration Test

Thank You

Sogeti USA

Chris Rice

[email protected]


Scott Teeters

[email protected]

more information