1.3. Vulnerability Assessment

Given time, resources, and motivation, an attacker can break into nearly any system. All of the security procedures and technologies currently available cannot guarantee that any systems are completely safe from intrusion. Routers help secure gateways to the Internet. Firewalls help secure the edge of the network. Virtual Private Networks safely pass data in an encrypted stream. Intrusion detection systems warn you of malicious activity. However, the success of each of these technologies is dependent upon a number of variables, including:
  • The expertise of the staff responsible for configuring, monitoring, and maintaining the technologies.
  • The ability to patch and update services and kernels quickly and efficiently.
  • The ability of those responsible to keep constant vigilance over the network.
Given the dynamic state of data systems and technologies, securing corporate resources can be quite complex. Due to this complexity, it is often difficult to find expert resources for all of your systems. While it is possible to have personnel knowledgeable in many areas of information security at a high level, it is difficult to retain staff who are experts in more than a few subject areas. This is mainly because each subject area of information security requires constant attention and focus. Information security does not stand still.
A vulnerability assessment is an internal audit of your network and system security; the results of which indicate the confidentiality, integrity, and availability of your network (as explained in Section 1.1.1, “Standardizing Security”). Typically, vulnerability assessment starts with a reconnaissance phase, during which important data regarding the target systems and resources is gathered. This phase leads to the system readiness phase, whereby the target is essentially checked for all known vulnerabilities. The readiness phase culminates in the reporting phase, where the findings are classified into categories of high, medium, and low risk; and methods for improving the security (or mitigating the risk of vulnerability) of the target are discussed
If you were to perform a vulnerability assessment of your home, you would likely check each door to your home to see if they are closed and locked. You would also check every window, making sure that they closed completely and latch correctly. This same concept applies to systems, networks, and electronic data. Malicious users are the thieves and vandals of your data. Focus on their tools, mentality, and motivations, and you can then react swiftly to their actions.

1.3.1. Defining Assessment and Testing

Vulnerability assessments may be broken down into one of two types: outside looking in and inside looking around.
When performing an outside-looking-in vulnerability assessment, you are attempting to compromise your systems from the outside. Being external to your company provides you with the cracker's viewpoint. You see what a cracker sees — publicly-routable IP addresses, systems on your DMZ, external interfaces of your firewall, and more. DMZ stands for "demilitarized zone", which corresponds to a computer or small subnetwork that sits between a trusted internal network, such as a corporate private LAN, and an untrusted external network, such as the public Internet. Typically, the DMZ contains devices accessible to Internet traffic, such as Web (HTTP) servers, FTP servers, SMTP (e-mail) servers and DNS servers.
When you perform an inside-looking-around vulnerability assessment, you are at an advantage since you are internal and your status is elevated to trusted. This is the viewpoint you and your co-workers have once logged on to your systems. You see print servers, file servers, databases, and other resources.
There are striking distinctions between the two types of vulnerability assessments. Being internal to your company gives you more privileges than an outsider. In most organizations, security is configured to keep intruders out. Very little is done to secure the internals of the organization (such as departmental firewalls, user-level access controls, and authentication procedures for internal resources). Typically, there are many more resources when looking around inside as most systems are internal to a company. Once you are outside the company, your status is untrusted. The systems and resources available to you externally are usually very limited.
Consider the difference between vulnerability assessments and penetration tests. Think of a vulnerability assessment as the first step to a penetration test. The information gleaned from the assessment is used for testing. Whereas the assessment is undertaken to check for holes and potential vulnerabilities, the penetration testing actually attempts to exploit the findings.
Assessing network infrastructure is a dynamic process. Security, both information and physical, is dynamic. Performing an assessment shows an overview, which can turn up false positives and false negatives. A false positive is a result, where the tool finds vulnerabilities which in reality do not exist. A false negative is when it omits actual vulnerabilities.
Security administrators are only as good as the tools they use and the knowledge they retain. Take any of the assessment tools currently available, run them against your system, and it is almost a guarantee that there are some false positives. Whether by program fault or user error, the result is the same. The tool may find false positives, or, even worse, false negatives.
Now that the difference between a vulnerability assessment and a penetration test is defined, take the findings of the assessment and review them carefully before conducting a penetration test as part of your new best practices approach.


Do not attempt to exploit vulnerabilities on production systems. Doing so can have adverse effects on productivity and efficiency of your systems and network.
The following list examines some of the benefits to performing vulnerability assessments.
  • Creates proactive focus on information security.
  • Finds potential exploits before crackers find them.
  • Results in systems being kept up to date and patched.
  • Promotes growth and aids in developing staff expertise.
  • Abates financial loss and negative publicity.

1.3.2. Establishing a Methodology for Vulnerability Assessment

To aid in the selection of tools for a vulnerability assessment, it is helpful to establish a vulnerability assessment methodology. Unfortunately, there is no predefined or industry approved methodology at this time; however, common sense and best practices can act as a sufficient guide.
What is the target? Are we looking at one server, or are we looking at our entire network and everything within the network? Are we external or internal to the company? The answers to these questions are important as they help determine not only which tools to select but also the manner in which they are used.
To learn more about establishing methodologies, see the following website:

1.3.3. Vulnerability Assessment Tools

An assessment can start by using some form of an information-gathering tool. When assessing the entire network, map the layout first to find the hosts that are running. Once located, examine each host individually. Focusing on these hosts requires another set of tools. Knowing which tools to use may be the most crucial step in finding vulnerabilities.
Just as in any aspect of everyday life, there are many different tools that perform the same job. This concept applies to performing vulnerability assessments as well. There are tools specific to operating systems, applications, and even networks (based on the protocols used). Some tools are free; others are not. Some tools are intuitive and easy to use, while others are cryptic and poorly documented but have features that other tools do not.
Finding the right tools may be a daunting task and, in the end, experience counts. If possible, set up a test lab and try out as many tools as you can, noting the strengths and weaknesses of each. Review the README file or man page for the tools. Additionally, look to the Internet for more information, such as articles, step-by-step guides, or even mailing lists specific to the tools.
The tools discussed below are just a small sampling of the available tools. Scanning Hosts with Nmap

Nmap is a popular tool that can be used to determine the layout of a network. Nmap has been available for many years and is probably the most often used tool when gathering information. An excellent manual page is included that provides detailed descriptions of its options and usage. Administrators can use Nmap on a network to find host systems and open ports on those systems.
Nmap is a competent first step in vulnerability assessment. You can map out all the hosts within your network and even pass an option that allows Nmap to attempt to identify the operating system running on a particular host. Nmap is a good foundation for establishing a policy of using secure services and restricting unused services.
To install Nmap, run the yum install nmap command as the root user. Using Nmap
Nmap can be run from a shell prompt by typing the nmap command followed by the host name or IP address of the machine to scan:
nmap <hostname>
For example, to scan a machine with host name foo.example.com, type the following at a shell prompt:
~]$ nmap foo.example.com
The results of a basic scan (which could take up to a few minutes, depending on where the host is located and other network conditions) look similar to the following:
Interesting ports on foo.example.com:
Not shown: 1710 filtered ports
22/tcp  open   ssh
53/tcp  open   domain
80/tcp  open   http
113/tcp closed auth
Nmap tests the most common network communication ports for listening or waiting services. This knowledge can be helpful to an administrator who wants to close unnecessary or unused services.
For more information about using Nmap, see the official homepage at the following URL: Nessus

Nessus is a full-service security scanner. The plug-in architecture of Nessus allows users to customize it for their systems and networks. As with any scanner, Nessus is only as good as the signature database it relies upon. Fortunately, Nessus is frequently updated and features full reporting, host scanning, and real-time vulnerability searches. Remember that there could be false positives and false negatives, even in a tool as powerful and as frequently updated as Nessus.


The Nessus client and server software requires a subscription to use. It has been included in this document as a reference to users who may be interested in using this popular application.
For more information about Nessus, see the official website at the following URL: OpenVAS

OpenVAS (Open Vulnerability Assessment System) is a set of tools and services that can be used to scan for vulnerabilities and for a comprehensive vulnerability management. The OpenVAS framework offers a number of web-based, desktop, and command line tools for controlling the various components of the solution. The core functionality of OpenVAS is provided by a security scanner, which makes use of over 33 thousand daily-updated Network Vulnerability Tests (NVT). Unlike Nessus (see Section, “Nessus), OpenVAS does not require any subscription.
For more information about OpenVAS, see the official website at the following URL: Nikto

Nikto is an excellent common gateway interface (CGI) script scanner. Nikto not only checks for CGI vulnerabilities but does so in an evasive manner, so as to elude intrusion-detection systems. It comes with thorough documentation which should be carefully reviewed prior to running the program. If you have web servers serving CGI scripts, Nikto can be an excellent resource for checking the security of these servers.
More information about Nikto can be found at the following URL: