1.2.2. 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 attacker's viewpoint. You see what an attacker 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 on the system 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.

Warning

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 attackers 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.

1.2.2.1. Establishing a Methodology

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 websites: