Suppose that you administer an enterprise network. Such networks are commonly comprised of operating systems, applications, servers, network monitors, firewalls, intrusion detection systems, and more. Now imagine trying to keep current with each of these. Given the complexity of today's software and networking environments, exploits and bugs are a certainty. Keeping current with patches and updates for an entire network can prove to be a daunting task in a large organization with heterogeneous systems.

Combine the expertise requirements with the task of keeping current, and it is inevitable that adverse incidents occur, systems are breached, data is corrupted, and service is interrupted.

To augment security technologies and aid in protecting systems, networks, and data, you must think like a cracker and gauge the security of your systems by checking for weaknesses. Preventative vulnerability assessments against your own systems and network resources can reveal potential issues that can be addressed before a cracker exploits it.

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 41.1.1.3, “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.

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 somewhat 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 these two types of vulnerability assessments. Being internal to your company gives you elevated privileges more so than any outsider. Still today in most organizations, security is configured in such a manner as to keep intruders out. Very little is done to secure the internals of the organization (such as departmental firewalls, user-level access controls, authentication procedures for internal resources, and more). Typically, there are many more resources when looking around inside as most systems are internal to a company. Once you set yourself outside of the company, you immediately are given an untrusted status. 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 checking 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.

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 vulnerabilities which in reality do not exist (false positive); or, even worse, the tool may not find vulnerabilities that actually do exist (false negative).

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.

The following list examines some of the benefits to performing vulnerability assessments.

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 tool. Additionally, look to the Internet for more information, such as articles, step-by-step guides, or even mailing lists specific to a tool.

The tools discussed below are just a small sampling of the available tools.

nmap foo.example.com

Starting nmap V. 3.50 ( www.insecure.org/nmap/ )
Interesting ports on localhost.localdomain (127.0.0.1):
(The 1591 ports scanned but not shown below are in state: closed)
Port       State       Service
22/tcp     open        ssh
25/tcp     open        smtp
111/tcp    open        sunrpc
443/tcp    open        https
515/tcp    open        printer
950/tcp    open        oftep-rpc
6000/tcp   open        X11

Nmap run completed -- 1 IP address (1 host up) scanned in 71.825 seconds