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Building Virtual Pentesting Labs for Advanced Penetration Testing
Table of Contents
Building Virtual Pentesting Labs for Advanced Penetration Testing
Credits
About the Author
About the Reviewers
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Preface
What this book covers
What you need for this book
Who this book is for
Conventions
Reader feedback
Customer support
Errata
Piracy
Questions
1. Introducing Penetration Testing
Security testing
Authentication
Authorization
Confidentiality
Integrity
Availability
Non-repudiation
Abstract testing methodology
Planning
Nonintrusive target search
Intrusive target search
Data analysis
Reporting
Myths and misconceptions of pen testing
Summary
2. Choosing the Virtual Environment
Open source and free environments
VMware Player
VirtualBox
Xen
Hyper-V
vSphere Hypervisor
Commercial environments
vSphere
VMware Player Plus
XenServer
VMware Workstation
Image conversion
Converting from a physical to virtual environment
Summary
3. Planning a Range
Planning
What are we trying to accomplish?
By when do we have to accomplish it?
Identifying vulnerabilities
Vulnerability sites
Vendor sites
Summary
4. Identifying Range Architecture
Building the machines
Building new machines
Conversion
Cloning a virtual machine
Selecting network connections
The bridged setting
Network Address Translation
The host-only switch
The custom settings
Choosing range components
The attacker machine
Router
Firewall
Web server
Summary
5. Identifying a Methodology
The OSSTMM
The Posture Review
Logistics
Active detection verification
Visibility Audit
Access verification
Trust verification
Control verification
Process verification
Configuration verification
Property validation
Segregation review
Exposure verification
Competitive intelligence scouting
Quarantine verification
Privileges audit
Survivability validation
Alert and log review
CHECK
NIST SP-800-115
The information security assessment methodology
Technical assessment techniques
Comparing tests and examinations
Testing viewpoints
Overt and covert
Offensive Security
Other methodologies
Customization
Summary
6. Creating an External Attack Architecture
Establishing layered architectures
Configuring firewall architectures
iptables
Deploying IDS/IPS and load balancers
Intrusion Detection System (IDS)
Intrusion Prevention System (IPS)
Load balancers
Integrating web application firewalls
Summary
7. Assessment of Devices
Assessing routers
Evaluating switches
MAC attacks
VLAN hopping attacks
GARP attacks
Attacking the firewall
Identifying the firewall rules
Tricks to penetrate filters
Summary
8. Architecting an IDS/IPS Range
Deploying a network-based IDS
Implementing the host-based IDS and endpoint security
Working with virtual switches
Evasion
Determining thresholds
Stress testing
Shell code obfuscation
Summary
9. Assessment of Web Servers and Web Applications
Analyzing the OWASP Top Ten attacks
Injection flaws
Broken authentication and session management
Cross-Site Scripting
Insecure direct object references
Security misconfiguration
Sensitive data exposure
Missing function-level access control
Cross-Site Request Forgery
Using known vulnerable components
Invalidated redirects and forwards
Identifying web application firewalls
Penetrating web application firewalls
Tools
Summary
10. Testing Flat and Internal Networks
The role of Vulnerability Scanners
Microsoft Baseline Security Analyzer
Open Vulnerability Assessment Language
Scanning without credentials
Nessus
Scanning with credentials
Dealing with host protection
User Account Control
The host firewall
Endpoint protection
Enhanced Mitigation Experience Toolkit
Summary
11. Attacking Servers
Common protocols and applications for servers
Web
File Transfer Protocol
Protocol research
Secure Shell
Database assessment
MSSQL
MySQL
Oracle
OS platform specifics
Windows legacy
Windows Server 2008 and 2012
Unix
Linux
MAC
Summary
12. Exploring Client-side Attack Vectors
Client-side attack methods
Bait
Lure
Pilfering data from the client
Using the client as a pivot point
Pivoting
Proxy exploitation
Leveraging the client configuration
Client-side exploitation
Binary payloads
Malicious PDF files
Bypassing antivirus and other protection tools
Obfuscation and encoding
Summary
13. Building a Complete Cyber Range
Creating the layered architecture
Architecting the switching
Segmenting the architecture
A public DMZ
A private DMZ
Decoy DMZ
Integrating decoys and honeypots
Attacking the cyber range
Recording the attack data for further training and analysis
Summary
Index
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