Hands-On Ethical Hacking and Network Defense, Third Edition 8-1
Chapter 8
Desktop and Server OS Vulnerabilities
At a Glance
Instructor’s Manual Table of Contents
Overview
Objectives
Teaching Tips
Quick Quizzes
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Lecture Notes
Overview
This chapter examines how security testing is used to analyze operating system vulnerabilities
and correct them. It reviews how to discover and fix these vulnerabilities on Windows, as well
as Linux operating systems. Students will learn about the available assessment tools, in
addition to several countermeasures for making these operating systems less vulnerable to
common problems.
Chapter Objectives
After reading this chapter and completing the exercises, the student will be able to:
Describe vulnerabilities of the Windows and Linux operating systems
Identify specific vulnerabilities and explain ways to fix them
Explain techniques to harden Windows and Linux systems
Teaching Tips
Windows OS Vulnerabilities
1. Explain that this section describes several tools used to discover vulnerabilities on
2. Explain to students that they can check the CVE and CERT Web sites to determine
vulnerabilities for any OS.
4. Remind students that exploits against these vulnerabilities should only be used in
specific cases, as a security tester and with prior approval.
5. Point out that tools like Nessus and OpenVAS will help to automate some of the
Windows File Systems
1. Describe the purpose of a file system. Regardless of the OS, the purpose of a file system
3. Explain the New Technology File System (NTFS). First released as a high-end file
Remote Procedure Call (RPC)
1. Describe RPC as an interprocess communication mechanism that allows a program
2. Explain how to use MBSA to determine if a system is vulnerable to an RPC-related
issue.
Security
Tip
Read http://www.microsoft.com/technet/security/bulletin/MS03-026.mspx and
http://www.microsoft.com/technet/security/bulletin/MS04-012.mspx for more
examples of RPC-related issues.
NetBIOS
1. Mention that NetBIOS has already been introduced in Chapter 6. Emphasize the fact
2. Describe NetBEUI as a fast, efficient network protocol that allows NetBIOS packets to
be transmitted over TCP/IP.
3. Explain that systems running newer Windows OSs can share files and resources without
using NetBIOS; however, NetBIOS is still used for backward compatibility, which is
Server Message Block
2. Mention that hacking tools for SMB include L0phtcrack’s SMB Packet Capture utility
Common Internet File System (CIFS)
1. Explain the Common Internet File System (CIFS), which is an enhanced version of
2. Describe the main characteristics of CIFS as explained in this chapter. In particular,
3. Discuss the two methods for server security an administrator can select:
Null Sessions
1. Describe null sessions as anonymous connections established without credentials.
Web Services
1. Explain the main problems of having a Web server installed on your network and
provide some recommendations to better secure it.
3. Explain that although IIS 6.0 (Windows Server 2003) through IIS 10.0 (Windows
4. Emphasize that regardless of the IIS version a system runs, keeping systems patched is
MS SQL Server
1. Describe the most common critical SQL vulnerability, the null SA password.
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Teaching
Tip
Visit http://www.sqlsecurity.com/, a Web site dedicated to explain Microsoft
SQL Server security issues.
Buffer Overflows
1. Describe the various buffer overflow problems. A buffer overflow occurs when data is
Passwords and Authentication
1. Explain why a comprehensive password policy is critical.
2. Describe the aspects that a password policy should include. Here are some examples:
a. Change password regularly
b. Require passwords length of at least six characters
3. Give some recommendations about configuring domain controllers. A good security or
network administrator should enforce password age, length, and complexity at the
domain controller. Also, the administrator should specify the account lockout threshold
and duration.
Teaching
Tip
Read http://www.techrepublic.com/article/lock-it-down-make-a-password-
policy-part-of-your-security-plan/ for an article on how to create a password
policy.
Tools for Identifying Vulnerabilities in Windows
1. Explain that many tools are available for discovering Windows vulnerabilities. Using
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Built-in Windows Tools
2. Using Table 8-2, summarize MBSA’s scanning capabilities.
3. Discuss the minimum system requirements for MBSA provided in Table 8-3.
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Disable Unused Services and Filtering Ports
2. Explain how filtering out unnecessary ports can protect systems from attack. Discuss
some of the ports frequently subject to attack.
Other Security Best Practices
1. Mention other security best practices, including the following steps:
a. Minimize the number of users with administrative rights
b. Implement software to prevent sensitive data from leaving the network
c. Use network segmentation
d. Restrict number of applications allowed to execute
Quick Quiz 1
1. True or False: The purpose of any file system, regardless of the OS, is to store and
manage information.
2. An interprocess communication mechanism that allows a program running on one host
to run code on a remote host is known as which of the following?
A. CIFS
B. MBSA
C. RPC
D. NetBIOS
3. True or False: Network resources are identified with 24-byte NetBIOS names.
4. True or False: NetBIOS is a network protocol.
5. Which protocol replaced SMB for Windows 2000 Server and later?
A. CIFS
B. RPC
C. NetBIOS
D. MBSA
Linux OS Vulnerabilities
1. Explain that like any OS, Linux can be made more secure if users are aware of its
vulnerabilities and keep current on new releases and fixes.
2. Mention that a typical Linux distribution has thousands of packages developed by many
contributors around the world. With such diverse sources of code, it’s inevitable that
flaws will happen.
Teaching
Tip
Visit http://www.linuxsecurity.com for recent news topics and articles regarding
Linux security.
Samba
1. Introduce Samba as an open-source implementation of CIFS. It was created in 1992 by
3. Describe how to configure and use Samba in mixed Windows and *nix environments to
allow both OSs to share files and printers.
Teaching
Tip
For more information, visit http://www.samba.org, the official Samba Web site.
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Tools for Identifying Linux Vulnerabilities
1. Mention that visiting the CVE Web site is a good first step in discovering possible
avenues attackers might take to break into a Linux system.
3. Explain what a security tester using enumeration tools can do:
a. Identify a computer on the network by using port scanning and zone transfers
4. Demonstrate how to use OpenVAS using Figures 8-4 through 8-12.
5. Explain how Trojan programs are used to carry out attacks. Most Trojan programs
perform one or more of the following functions:
a. Allow remote administration of the attacked system.
6. Mention that even more dangerous are rootkits containing Trojan binary programs
ready to be installed by an intruder who has gained root access to a system.
Security
Tip
Check out http://nvd.nist.gov/nvd.cfm?cvename=CVE-2004-0075 for an
example of a Linux vulnerability.
More Countermeasures Against Linux Attacks
1. Explain the most critical tasks for protecting against attacks. They include:
a. User awareness training
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Teaching
Tip
The following link contains a quick reference guide for Linux security:
http://tldp.org/REF/ls_quickref/QuickRefCard.pdf.
Quick Quiz 2
1. True or False: A typical Linux distribution has thousands of packages developed by
many contributors around the world.
2. To address the issue of interoperability, what was created as an open-source
implementation of CIFS?
A. Ubuntu
B. Samba
C. Debian
D. Red Hat Package Manager
3. True or False: OpenVAS can only be used to enumerate Windows OSs.
4. Which of the following is a dangerous vulnerability containing Trojan binary programs
ready to be installed by an intruder who has gained root access to a system?
A. Bash bug
B. Shellshock
C. rootkit
D. zone transfer
5. What feature is an OS security mechanism that enforces access rules based on
privileges for interactions between processes, files, and users?
Class Discussion Topics
1. Many argue that Windows systems only appear to be the most vulnerable systems
because they have more of the market share. Do you agree or disagree with this
statement? Why?
2. What are the problems with using blank passwords? Why do you think Windows insists
on using a blank password for the SA account when you install SQL Server?
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Additional Projects
1. Ask your students to investigate the pros and cons of Microsoft Baseline Security
2. The problem with weak passwords is that they can easily be guessed using automated
tools. In this project, you will follow a two-step approach to uncover Windows
passwords. First download, install, and run a tool called PWDump to obtain an
encrypted list of all user names and passwords. Second, download and run John the
Additional Resources
2. Microsoft Baseline Security Analyzer:
3. SANS Institute CIS Critical Security Controls:
5. Extended Stored Procedures: Intro And 10 Cool Examples:
Key Terms
See Glossary for definitions for Key Terms.
attack surface
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domain controller
Mandatory Access Control (MAC)
NetBIOS Extended User Interface (NetBEUI)
Technical Notes for Activities
Activity 8-1: This activity requires a computer running Windows, an Internet connection,
and a Web browser.
Activity 8-2: This activity requires a computer running Windows with MBSA already