Scott Teeters, Jr. MicroSolved, Inc. in partnership with Sogeti USA How to Fail A Penetration Test Concepts in Securing a Network

Scott Teeters, Jr.

MicroSolved, Inc.

in partnership with

Sogeti USA

How to Fail A Penetration TestConcepts in Securing a Network

http://www.secureassure.com

Background

• 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

• Common issues that cause an organization to fail penetration tests

• Some suggestions on how an organization may improve their security posture


Note:

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


> Policy Issues


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

• 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


Example:

• 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:

• Poor Domain Trust ChoicesWho

trusts who?

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

Production

Development


Example:

Production

Development

• Good Domain Trust ChoicesWho

trusts who?

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


Process Issues:

• Information Leakage ProblemsWho’s saying

what?

– Example of Usenet leakage

"Gary Smith" <Gary [email protected]> wrote in message news:#nKxhAAGAHA.281@cppssbbsa04...

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:

• Combating Information LeakageWho’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


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

• Sometimes, patches have to be applied in a specific order or manner

– Failing to do so, may actually INCREASE your vulnerability!


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 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

• 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

• 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

• 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

• 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?

REGULAR ASSESSMENT & MONITORING


How To Fail A Penetration Test

1. Implement poor policies and processes• No policies and processes also count!

2. Mismanage patches and fixes3. Misconfigure your perimeter, network

and/or systems4. Take a number, attackers will be right

with you…

more information

Sogeti USA

http://www.sogeti-usa.com

Chris Rice

[email protected]

Or

Scott Teeters

[email protected]

Thank You

Documents

Scott Teeters, Jr. MicroSolved, Inc. in partnership with Sogeti USA How to Fail A Penetration Test Concepts in Securing a Network