Ethical Hacking

Introduction to Ethical Hacking
In This Chapter
Understanding hacker objectives
Outlining the differences between ethical hackers and malicious hackers
Examining how the ethical hacking process has come about
Understanding the dangers that your computer systems face
Starting the ethical hacking process
This book is about hacking ethically — the science of testing your computers
and network for security vulnerabilities and plugging the holes you
find before the bad guys get a chance to exploit them.
Although ethical is an often overused and misunderstood word, the Merriam-
Webster dictionary defines ethical perfectly for the context of this book and
the professional security testing techniques that I cover — that is, conforming
to accepted professional standards of conduct. IT practitioners are obligated to
perform all the tests covered in this book aboveboard and only after permission
has been obtained by the owner(s) of the systems — hence the disclaimer
in the introduction.
How Hackers Beget Ethical Hackers
We’ve all heard of hackers. Many of us have even suffered the consequences
of hacker actions. So who are these hackers? Why is it important to know
about them? The next few sections give you the lowdown on hackers.
Defining hacker
Hacker is a word that has two meanings:
Traditionally, a hacker is someone who likes to tinker with software or
electronic systems. Hackers enjoy exploring and learning how computer
systems operate. They love discovering new ways to work electronically.
Recently, hacker has taken on a new meaning — someone who maliciously
breaks into systems for personal gain. Technically, these criminals are
crackers (criminal hackers). Crackers break into (crack) systems with
malicious intent. They are out for personal gain: fame, profit, and even
revenge. They modify, delete, and steal critical information, often making
other people miserable.
The good-guy (white-hat) hackers don’t like being in the same category as the
bad-guy (black-hat) hackers. (These terms come from Western movies where
the good guys wore white cowboy hats and the bad guys wore black cowboy
hats.) Whatever the case, most people give hacker a negative connotation.
Many malicious hackers claim that they don’t cause damage but instead are
altruistically helping others. Yeah, right. Many malicious hackers are electronic
In this book, I use the following terminology:
Hackers (or bad guys) try to compromise computers.
Ethical hackers (or good guys) protect computers against illicit entry.
Hackers go for almost any system they think they can compromise. Some
prefer prestigious, well-protected systems, but hacking into anyone’s system
increases their status in hacker circles.
Ethical Hacking 101
You need protection from hacker shenanigans. An ethical hacker possesses
the skills, mindset, and tools of a hacker but is also trustworthy. Ethical hackers
perform the hacks as security tests for their systems.
If you perform ethical hacking tests for customers or simply want to add
another certification to your credentials, you may want to consider the ethical
hacker certification Certified Ethical Hacker, which is sponsored by ECCouncil.
See for more information.
Ethical hacking — also known as penetration testing or white-hat hacking —
involves the same tools, tricks, and techniques that hackers use, but with one
major difference: Ethical hacking is legal. Ethical hacking is performed with
the target’s permission. The intent of ethical hacking is to discover vulnerabilities
from a hacker’s viewpoint so systems can be better secured. It’s part
of an overall information risk management program that allows for ongoing
security improvements. Ethical hacking can also ensure that vendors’ claims
about the security of their products are legitimate.
10 Part I: Building the Foundation for Ethical Hacking
To hack your own systems like the bad guys, you must think like they think.
It’s absolutely critical to know your enemy; see Chapter 2 for details.
Understanding the Need to
Hack Your Own Systems
To catch a thief, think like a thief. That’s the basis for ethical hacking.
The law of averages works against security. With the increased numbers and
expanding knowledge of hackers combined with the growing number of system
vulnerabilities and other unknowns, the time will come when all computer
systems are hacked or compromised in some way. Protecting your systems
from the bad guys — and not just the generic vulnerabilities that everyone
knows about — is absolutely critical. When you know hacker tricks, you can
see how vulnerable your systems are.
Hacking preys on weak security practices and undisclosed vulnerabilities.
Firewalls, encryption, and virtual private networks (VPNs) can create a false
feeling of safety. These security systems often focus on high-level vulnerabilities,
such as viruses and traffic through a firewall, without affecting how hackers
work. Attacking your own systems to discover vulnerabilities is a step to
making them more secure. This is the only proven method of greatly hardening
your systems from attack. If you don’t identify weaknesses, it’s a matter of
time before the vulnerabilities are exploited.
As hackers expand their knowledge, so should you. You must think like them
to protect your systems from them. You, as the ethical hacker, must know
activities hackers carry out and how to stop their efforts. You should know
what to look for and how to use that information to thwart hackers’ efforts.
You don’t have to protect your systems from everything. You can’t. The only
protection against everything is to unplug your computer systems and lock
them away so no one can touch them — not even you. That’s not the best
approach to information security. What’s important is to protect your systems
from known vulnerabilities and common hacker attacks.
It’s impossible to buttress all possible vulnerabilities on all your systems. You
can’t plan for all possible attacks — especially the ones that are currently
unknown. However, the more combinations you try — the more you test whole
systems instead of individual units — the better your chances of discovering
vulnerabilities that affect everything as a whole.
Don’t take ethical hacking too far, though. It makes little sense to harden your
systems from unlikely attacks. For instance, if you don’t have a lot of foot traffic
Chapter 1: Introduction to Ethical Hacking 11
in your office and no internal Web server running, you may not have as much
to worry about as an Internet hosting provider would have. However, don’t
forget about insider threats from malicious employees!
Your overall goals as an ethical hacker should be as follows:
Hack your systems in a nondestructive fashion.
Enumerate vulnerabilities and, if necessary, prove to upper management
that vulnerabilities exist.
Apply results to remove vulnerabilities and better secure your systems.
Understanding the Dangers
Your Systems Face
It’s one thing to know that your systems generally are under fire from hackers
around the world. It’s another to understand specific attacks against your systems
that are possible. This section offers some well-known attacks but is by
no means a comprehensive listing. That requires its own book: Hack Attacks
Encyclopedia, by John Chirillo (Wiley Publishing, Inc.).
Many information-security vulnerabilities aren’t critical by themselves.
However, exploiting several vulnerabilities at the same time can take its toll.
For example, a default Windows OS configuration, a weak SQL Server administrator
password, and a server hosted on a wireless network may not be
major security concerns separately. But exploiting all three of these vulnerabilities
at the same time can be a serious issue.
Nontechnical attacks
Exploits that involve manipulating people — end users and even yourself —
are the greatest vulnerability within any computer or network infrastructure.
Humans are trusting by nature, which can lead to social-engineering exploits.
Social engineering is defined as the exploitation of the trusting nature of human
beings to gain information for malicious purposes. I cover social engineering
in depth in Chapter 5.
Other common and effective attacks against information systems are physical.
Hackers break into buildings, computer rooms, or other areas containing critical
information or property. Physical attacks can include dumpster diving
(rummaging through trash cans and dumpsters for intellectual property,
passwords, network diagrams, and other information).
12 Part I: Building the Foundation for Ethical Hacking
Network-infrastructure attacks
Hacker attacks against network infrastructures can be easy, because many
networks can be reached from anywhere in the world via the Internet. Here
are some examples of network-infrastructure attacks:
Connecting into a network through a rogue modem attached to a
computer behind a firewall
Exploiting weaknesses in network transport mechanisms, such as TCP/IP
and NetBIOS
Flooding a network with too many requests, creating a denial of service
(DoS) for legitimate requests
Installing a network analyzer on a network and capturing every packet
that travels across it, revealing confidential information in clear text
Piggybacking onto a network through an insecure 802.11b wireless
Operating-system attacks
Hacking operating systems (OSs) is a preferred method of the bad guys. OSs
comprise a large portion of hacker attacks simply because every computer
has one and so many well-known exploits can be used against them.
Occasionally, some operating systems that are more secure out of the box —
such as Novell NetWare and the flavors of BSD UNIX — are attacked, and
vulnerabilities turn up. But hackers prefer attacking operating systems like
Windows and Linux because they are widely used and better known for their
Here are some examples of attacks on operating systems:
Exploiting specific protocol implementations
Attacking built-in authentication systems
Breaking file-system security
Cracking passwords and encryption mechanisms
Application and other specialized attacks
Applications take a lot of hits by hackers. Programs such as e-mail server
software and Web applications often are beaten down:
Chapter 1: Introduction to Ethical Hacking 13
Hypertext Transfer Protocol (HTTP) and Simple Mail Transfer Protocol
(SMTP) applications are frequently attacked because most firewalls and
other security mechanisms are configured to allow full access to these
programs from the Internet.
Malicious software (malware) includes viruses, worms, Trojan horses,
and spyware. Malware clogs networks and takes down systems.
Spam (junk e-mail) is wreaking havoc on system availability and storage
space. And it can carry malware.
Ethical hacking helps reveal such attacks against your computer systems.
Parts II through V of this book cover these attacks in detail, along with specific
countermeasures you can implement against attacks on your systems.
Obeying the Ethical Hacking
Every ethical hacker must abide by a few basic commandments. If not, bad
things can happen. I’ve seen these commandments ignored or forgotten when
planning or executing ethical hacking tests. The results weren’t positive.
Working ethically
The word ethical in this context can be defined as working with high professional
morals and principles. Whether you’re performing ethical hacking tests
against your own systems or for someone who has hired you, everything you
do as an ethical hacker must be aboveboard and must support the company’s
goals. No hidden agendas are allowed!
Trustworthiness is the ultimate tenet. The misuse of information is absolutely
forbidden. That’s what the bad guys do.
Respecting privacy
Treat the information you gather with the utmost respect. All information
you obtain during your testing — from Web-application log files to clear-text
passwords — must be kept private. Don’t use this information to snoop into
confidential corporate information or private lives. If you sense that someone
should know there’s a problem, consider sharing that information with the
appropriate manager.
14 Part I: Building the Foundation for Ethical Hacking
Involve others in your process. This is a “watch the watcher” system that can
build trust and support your ethical hacking projects.
Not crashing your systems
One of the biggest mistakes I’ve seen when people try to hack their own systems
is inadvertently crashing their systems. The main reason for this is poor
planning. These testers have not read the documentation or misunderstand
the usage and power of the security tools and techniques.
You can easily create DoS conditions on your systems when testing. Running
too many tests too quickly on a system causes many system lockups. I know
because I’ve done this! Don’t rush things and assume that a network or specific
host can handle the beating that network scanners and vulnerabilityassessment
tools can dish out.
Many security-assessment tools can control how many tests are performed
on a system at the same time. These tools are especially handy if you need to
run the tests on production systems during regular business hours.
You can even create an account or system lockout condition by social engineering
someone into changing a password, not realizing that doing so might
create a system lockout condition.
The Ethical Hacking Process
Like practically any IT or security project, ethical hacking needs to be planned
in advance. Strategic and tactical issues in the ethical hacking process should
be determined and agreed upon. Planning is important for any amount of
testing — from a simple password-cracking test to an all-out penetration test
on a Web application.
Formulating your plan
Approval for ethical hacking is essential. Make what you’re doing known and
visible — at least to the decision makers. Obtaining sponsorship of the project
is the first step. This could be your manager, an executive, a customer, or
even yourself if you’re the boss. You need someone to back you up and sign
off on your plan. Otherwise, your testing may be called off unexpectedly if
someone claims they never authorized you to perform the tests.
Chapter 1: Introduction to Ethical Hacking 15
The authorization can be as simple as an internal memo from your boss if
you’re performing these tests on your own systems. If you’re testing for a
customer, have a signed contract in place, stating the customer’s support and
authorization. Get written approval on this sponsorship as soon as possible
to ensure that none of your time or effort is wasted. This documentation is
your Get Out of Jail Free card if anyone questions what you’re doing.
You need a detailed plan, but that doesn’t mean you have to have volumes of
testing procedures. One slip can crash your systems — not necessarily what
anyone wants. A well-defined scope includes the following information:
Specific systems to be tested
Risks that are involved
When the tests are performed and your overall timeline
How the tests are performed
How much knowledge of the systems you have before you start testing
What is done when a major vulnerability is discovered
The specific deliverables — this includes security-assessment reports
and a higher-level report outlining the general vulnerabilities to be
addressed, along with countermeasures that should be implemented
When selecting systems to test, start with the most critical or vulnerable
systems. For instance, you can test computer passwords or attempt socialengineering
attacks before drilling down into more detailed systems.
It pays to have a contingency plan for your ethical hacking process in case
something goes awry. What if you’re assessing your firewall or Web application,
and you take it down? This can cause system unavailability, which can
reduce system performance or employee productivity. Even worse, it could
cause loss of data integrity, loss of data, and bad publicity.
Handle social-engineering and denial-of-service attacks carefully. Determine
how they can affect the systems you’re testing and your entire organization.
Determining when the tests are performed is something that you must think
long and hard about. Do you test during normal business hours? How about
late at night or early in the morning so that production systems aren’t affected?
Involve others to make sure they approve of your timing.
The best approach is an unlimited attack, wherein any type of test is possible.
The bad guys aren’t hacking your systems within a limited scope, so why
should you? Some exceptions to this approach are performing DoS, socialengineering,
and physical-security tests.
Don’t stop with one security hole. This can lead to a false sense of security.
Keep going to see what else you can discover. I’m not saying to keep hacking
16 Part I: Building the Foundation for Ethical Hacking
until the end of time or until you crash all your systems. Simply pursue the
path you’re going down until you can’t hack it any longer (pun intended).
One of your goals may be to perform the tests without being detected. For
example, you may be performing your tests on remote systems or on a remote
office, and you don’t want the users to be aware of what you’re doing. Otherwise,
the users may be on to you and be on their best behavior.
You don’t need extensive knowledge of the systems you’re testing — just a
basic understanding. This will help you protect the tested systems.
Understanding the systems you’re testing shouldn’t be difficult if you’re hacking
your own in-house systems. If you’re hacking a customer’s systems, you
may have to dig deeper. In fact, I’ve never had a customer ask for a fully blind
assessment. Most people are scared of these assessments. Base the type of
test you will perform on your organization’s or customer’s needs.
Chapter 19 covers hiring “reformed” hackers.
Selecting tools
As with any project, if you don’t have the right tools for ethical hacking, accomplishing
the task effectively is difficult. Having said that, just because you use
the right tools doesn’t mean that you will discover all vulnerabilities.
Know the personal and technical limitations. Many security-assessment tools
generate false positives and negatives (incorrectly identifying vulnerabilities).
Others may miss vulnerabilities. If you’re performing tests such as socialengineering
or physical-security assessments, you may miss weaknesses.
Many tools focus on specific tests, but no one tool can test for everything.
For the same reason that you wouldn’t drive in a nail with a screwdriver, you
shouldn’t use a word processor to scan your network for open ports. This is
why you need a set of specific tools that you can call on for the task at hand.
The more tools you have, the easier your ethical hacking efforts are.
Make sure you that you’re using the right tool for the task:
To crack passwords, you need a cracking tool such as LC4, John the
Ripper, or pwdump.
A general port scanner, such as SuperScan, may not crack passwords.
For an in-depth analysis of a Web application, a Web-application assessment
tool (such as Whisker or WebInspect) is more appropriate than a
network analyzer (such as Ethereal).
Chapter 1: Introduction to Ethical Hacking 17
When selecting the right security tool for the task, ask around. Get advice
from your colleagues and from other people online. A simple Groups search
on Google ( or perusal of security portals, such as,, and, often produces
great feedback from other security experts.
Hundreds, if not thousands, of tools can be used for ethical hacking — from
your own words and actions to software-based vulnerability-assessment programs
to hardware-based network analyzers. The following list runs down
some of my favorite commercial, freeware, and open-source security tools:
LC4 (formerly called L0phtcrack)
LANguard Network Security Scanner
Network Stumbler
Here are some other popular tools:
Internet Scanner
I discuss these tools and many others in Parts II through V when I go into the
specific hack attacks. Appendix A contains a more comprehensive listing of
these tools for your reference.
The capabilities of many security and hacking tools are often misunderstood.
This misunderstanding has shed negative light on some excellent tools, such
as SATAN (Security Administrator Tool for Analyzing Networks) and Nmap
(Network Mapper).
Some of these tools are complex. Whichever tools you use, familiarize yourself
with them before you start using them. Here are ways to do that:
18 Part I: Building the Foundation for Ethical Hacking
Read the readme and/or online help files for your tools.
Study the user’s guide for your commercial tools.
Consider formal classroom training from the security-tool vendor or
another third-party training provider, if available.
Look for these characteristics in tools for ethical hacking:
Adequate documentation.
Detailed reports on the discovered vulnerabilities, including how they
may be exploited and fixed.
Updates and support when needed.
High-level reports that can be presented to managers or nontechie types.
These features can save you time and effort when you’re writing the report.
Executing the plan
Ethical hacking can take persistence. Time and patience are important. Be
careful when you’re performing your ethical hacking tests. A hacker in your
network or a seemingly benign employee looking over your shoulder may
watch what’s going on. This person could use this information against you.
It’s not practical to make sure that no hackers are on your systems before
you start. Just make sure you keep everything as quiet and private as possible.
This is especially critical when transmitting and storing your test results.
If possible, encrypt these e-mails and files using Pretty Good Privacy (PGP) or
something similar. At a minimum, password-protect them.
You’re now on a reconnaissance mission. Harness as much information as
possible about your organization and systems, which is what malicious hackers
do. Start with a broad view and narrow your focus:
1. Search the Internet for your organization’s name, your computer and
network system names, and your IP addresses.
Google is a great place to start for this.
2. Narrow your scope, targeting the specific systems you’re testing.
Whether physical-security structures or Web applications, a casual
assessment can turn up much information about your systems.
3. Further narrow your focus with a more critical eye. Perform actual
scans and other detailed tests on your systems.
4. Perform the attacks, if that’s what you choose to do.
Chapter 1: Introduction to Ethical Hacking 19
Evaluating results
Assess your results to see what you uncovered, assuming that the vulnerabilities
haven’t been made obvious before now. This is where knowledge counts.
Evaluating the results and correlating the specific vulnerabilities discovered
is a skill that gets better with experience. You’ll end up knowing your systems
as well as anyone else. This makes the evaluation process much simpler
moving forward.
Submit a formal report to upper management or to your customer, outlining
your results. Keep these other parties in the loop to show that your efforts
and their money are well spent. Chapter 17 describes this process.
Moving on
When you’ve finished your ethical hacking tests, you still need to implement
your analysis and recommendations to make sure your systems are secure.
New security vulnerabilities continually appear. Information systems constantly
change and become more complex. New hacker exploits and security
vulnerabilities are regularly uncovered. You may discover new ones! Security
tests are a snapshot of the security posture of your systems. At any time,
everything can change, especially after software upgrades, adding computer
systems, or applying patches. Plan to test regularly (for example, once a
week or once a month).

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