Penetration testing or pen testing, or ethical hacking, is an attack imitation or simulation procedure that organizations employ to scrutinize, find and fish out weak entry spots in their security systems.

Penetration testing usually comprises intentional cyber-attacks on a company’s application systems and servers. This impersonation is typically done to find vulnerabilities in an organization’s computer systems, break through the loopholes and get access to its data for as long as possible before the intrusion is detected.

Organizations employ professionals known as penetration testers to perform these vulnerability tests. These professionals can be hired from third-party organizations or even be employees of the organizations themselves.

Imitating a real-life hacker’s slippery tactics and crafty movements gives the organization proof of the safety of their applications and computer systems or otherwise. Another reason why organizations run penetration testing is for compliance regulations.

In this article, we will look at all you need to know about penetration testing. First, let us look into what we mean by penetration itself.

What is penetration?

Penetration means the depth to which a hacker can gain and maintain access through a target’s vulnerabilities. In other words, how long and how far a cyber attack can occur in an organization’s application systems before it is detected.

We have defined what penetration and penetration testing are, but why are we testing? What is the main goal of penetration testing?

What is the main goal of penetration testing?

The objective of penetration testing is to appraise the viability of current systems and assess the level of damage a potential hack can have on existing resources or organizational data.

Subsequently, after penetration testing, the risks about the uncovered weak spots are collected and sent to the concerned departments, i.e. the security and system managers. They make their inference, map out corrective measures and build stronger defense systems.

Before we go into the penetration testing stages, let’s get you prepared first.

How do I prepare for penetration testing?

Considering the significance of penetration testing, you might be bothered about what happens before or when the testing commences. These concerns are justified, as they are mostly around possible network shutdown, which takes its toll on the smooth running of the business.

However, to allay your fears, here are a few ways to prepare for an upcoming penetration testing in your organization.

Penetration testers use a variety of equipment. Here are some examples of what they use.

This is the WiFi Pineapple, it’s used for WifI penetration testing. Take a look!


Tip 1: Inform your IT team

This may sound like public knowledge, but you should put your IT team in the know of any upcoming testing except in the case of double-blind testing, which I will explain later.

If your internal team is not informed of the development, they might be led to believe something else is happening and begin their procedures to salvage the situation. This response to the unannounced testing then makes the penetration testing process strenuous.

Besides informing your team, you should have someone who will be the technical contact person for your organization with the third-party ethical hacking firm if you are hiring a third party.

Tip 2: Plan a time frame for fixes

The report of penetration testing usually comes with recommended fixes. It is therefore advisable you also plan a time frame that will cover and rectify the issues highlighted. Dealing with these threats may be time-consuming, but fixing them will result in upgraded security systems for your organization.

Tip 3: Determine the scope of the penetration test

As an organization, you should know before testing the environment and scope of the test to ensure the penetration testers have the necessary access and permission to proceed. Also, try not to restrict the scope of penetration testing. This might reduce it to a mere vulnerability scan – this will be explained later in the article.

Tip 4: Prepare for network glitches

Normally, penetration testing should not bring about any application or network issues, but things happen, right? After all, testing can magnify any prevailing faults. Therefore, you want to have personnel on-ground that works with the ethical hackers and instantly fix any issue.

Note: Prior to the commencement of any penetration testing, ensure your data is backed up and easy to reach. This will save you precious time if a situation calls for a backup.

Now, let’s go to the stages of penetration testing.

What are the penetration testing stages?

The procedure for penetration testing can be understood clearly in the six stages below:

Stage 1: Planning

Before a penetration test, the organizations and the ethical hackers must be on the same page regarding several things. They need to align on the kind of tests to be run, what access the penetration testers will need, the environment, extent, and goal of the test.

The planning stage is a survey and investigation around the whats and whys of the test and systems to be tested. It includes:

  • Scope: Here, you describe the purview of the penetration testing, the computer systems, the appropriate testing methods, and finally, the objectives of the test.
  • Data collection: This involves aggregating data on the servers, networks, etc., to get useful, working information on a system’s weak spots.




Stage 2: Inspection

The inspection stage is a type of analysis performed on the target to get feedback on how the system will react to cyber-attack simulations. This can be examined through any of these two analyses.

  • Static: This analysis involves scanning all the code of an application in one go, in its non-running state, to get a picture of how the system will fare in its running state.
  • Dynamic: This analysis, as the name suggests, involves scanning in an application’s active state. It gives an actual-time evaluation of the system’s performance.




Stage 3: Penetration and Persistent access

At this stage, ethical hackers begin to penetrate the systems finding weak spots in the target’s security and capitalizing on them to get deeper and deeper access to data.

Penetration testers invade and exploit these weak spots with SQL injection and other intentional web application attacks to further see the extent of harm they can wreck.

They can also discover if these uncovered vulnerabilities are dangerous enough to allow continued, exploitative access into the system long enough for a real hacker to steal the organization’s sensitive data.

(penetration testers will often deploy USB Rubber Ducky tools, these can be loaded with Ducky scripts to perform extremely fast functions like keylogging or hash dumps)



Stage 4: Analysis

This stage aggregates the penetration testing report for the organization’s security personnel to take necessary actions.

The specifics in the report include the weak spots found, how they penetrated the system, what data or information was uncovered along the paths taken, how long they were able to go further in the system unnoticed, and suggestions on where to make amendments.




Stage 5: Making the necessary fixes

From the report of stage 4, your security personnel should now know where to start carrying out their remediation procedures to fortify their security systems. But before then, ensure that the penetration testers clear and clean up their paths. This is to prevent leaving clues behind for a real bad guy to grasp in the future.




Stage 6: Run the penetration test again

How would you know if your fixes are impenetrable? By testing. It is imperative to bear in mind that new ways of cyber attacks are unfolding, so it is best to anticipate that there will be new defects and vulnerabilities.

What are the penetration testing methods?

Here, we will look at the five methods for penetration testing.


Method 1: Blind testing

Blind testing only lets the penetration tester have the name of the target, nothing more. With this, an organization’s security personnel can observe how a real-life cyber invasion happens.


Method 2: Double-blind testing

Here, an organization’s security personnel are unaware of the pen-testing. Like the shock a hack brings in real life, they will have no time to defend against the penetration.



Method 3: Internal testing

For internal testing, a breach is simulated from the perspective of a malevolent insider, i.e. penetration testing with a behind-the-firewall approach.


Method 4: External testing

External testing is more like the opposite of internal testing. It takes a before-the-firewall approach, i.e. penetration testing on the more visible resources of an organization on the internet.


Method 5: Targeted testing

This is the direct opposite of double-blind testing. In this testing case, there is a synergy between both parties (clients and pen testers). Both sides are in sync with the testing in real-time.

Now that we have learned the penetration testing methods let us look into some of the tools used for pen-testing.

What tools are used for penetration testing?

Here are the top ten penetration testing tools that have made the modern-day ethical hacker a cyborg in running pen-testing very efficiently.

1. Kali Linux

  • Previously called BackTrack Linux
  • Kali Linux is built for offensive use as a penetration tester.

2. Metasploit

  • The world’s most used penetration testing framework
  • Essential for defenders to guard their systems from attackers.

3. sqlmap

  • Open-source SQL injection tool
  • Gains control of database servers
  • Supports MySQL, H2, HSQLDB, Informix, SAP MaxDB, Sybase, Firebird, SQLite, IBM DB2, Microsoft Access, Microsoft SQL Server, PostgreSQL, and Oracle

4. nmap

  • nmap is the short version for network mapper
  • A port-scanning veteran and one of the best and tested pen-testing tools.

5. Zed Attack Proxy

  • Beginner-friendly tool to learn about and change web traffic
  • Zed Attack Proxy lets you waylay web traffic and alter it. 

6. Hashcat

  • Hashcat is the go-to pen-testing tool to crack hashes
  • It works best on a modern GPU

7. Wireshark

  • Wireshark helps you know the traffic across your network and analyze TCP/IP connection problems
  • Real-time protocol analysis and decryption support
  • A must-learn tool if you’re new to pen testing

8. Burp Suite

  • Very effective web vulnerability scanner
  • Pricey and mostly used by the pros.

9. John the Ripper

  • Breaks encryption
  • Open-source and is used for offline password cracking.
  • John the Ripper can transmute a word list of potential passwords and keep permutating until a password is found.

10. Hydra

  • Useful for online password cracking such as an RDP, IRC, IMAP, FTP or SSH login, etc.

Next, everything you need to know about pen testing is what makes penetration testing good or outstanding.


The Hak5 Bash Bunny allows an ethical hacker to load bash scripts on the device so he/she can emulate real world attacks against devices. You can see the product here


What should good penetration testing include?

After a penetration test, clients/organizations expect to receive a report or documentation that presents salient points regarding the pen testing while giving a practical course of action for the remediations. Here are three elements that comprise good penetration testing:

1) Executive Summary

An executive summary is a piece of communication on the penetration testing report that is plain and crystal clear to non-technical individuals. It comes from the business angle and highlights impending risks based on the findings of the pen-testing.

This then helps business leaders to make informed decisions on how best to salvage the situation and move the organization forward.

2) Impact Report from Technical and Business angles

Most times, the technical teams have to make swift decisions based on the penetration testing report. As important as these decisions are, they need clearance and go-ahead from the top-level executives.

However, these executives are not familiar with so many of the technical terms and terminologies. The only thing that will make these top executives see the urgency that you, as a technical team member, sees is if the report is put in a context the way they understand.

To the technical aspect, adding an angle that also shows how a potential risk could impact the business side of things brings more significance to the report. Now, quicker actions can be taken because the top executives can discern how the vulnerabilities could make a huge negative difference in the organization.

3) Remediation Alternatives

One more important element of a good penetration testing report is that it does not presume that the internal employees of an organization know how to fix all vulnerabilities.

Some pen reports just give one blanket remediation statement to an issue. This mostly lacks the personalization or the custom feels that the client truly desires. For example, suppose a weak spot was uncovered with a service on a web server instead of only saying they should disable it. In that case, you can also add other ways like firewall configuration and SQL injection filtering to counter these types of attacks.

A helpful and reliable penetration testing report that will help the client swiftly swing into action without headache should be one with multiple remediation options.

How many types of penetration testing are there?

It can be quite tempting to just tell an ethical hacker to test everything but don’t. In penetration testing, quality is always a better choice than quantity. The more focused a test is on a given area, the deeper the simulation attack and the more useful the results.

Therefore, to achieve the objectives you hope for, here are five specific areas you can choose from to focus on on your next penetration testing.


Network Penetration Tests

Here, network penetration testers centers on network security. They seek and uncover weak spots and loopholes on diverse network access. If an opening is found, they keep pulling the thread to maintain access and gain further ground into more crucial and sensitive data. The main goal of network penetration testing is to get to whatever vulnerabilities exist before a real-life hacker does.

Web Application Tests

Web application penetration testing takes a comprehensive approach to scrutinize web applications, checking flaws like injection vulnerabilities and coding errors.

IoT Penetration Tests

Here, ethical hackers analyze the layers of IoT devices to uncover hidden vulnerabilities that might have gone previously undetected.

Cloud Penetration Tests

Cloud penetration testing is focused on your cloud environment. It tries to identify any weak spots, verifies the safety of your deployments, and generally reports how to better enhance your cloud-based applications.

Social Engineering Test

Social engineering uses phishing scams to penetrate a system and exploit data. Penetration testers and ethical hackers commonly use phishing tools to assess and breach an organization’s firewall and get feedback on where reinforcement is needed.

Is penetration testing legal?

Yes, it is legal. I mentioned in the first heading of this article that organizations run penetration testing for compliance regulations. Penetration testing affords your organization the lucidity and honesty it needs to pass legal compliance and impartiality to address an impending attack.

How often should you pen test?

Pen testing should be done consistently simply because there is always something to be found. New waves of cyber attacks and threats are emerging, and you cannot be too relaxed. Lastly, let us look briefly into the difference between penetration testing and a vulnerability scan.

How does a penetration test differ from a vulnerability assessment or scan?

A vulnerability scan is an overview examination of a system environment. The scan usually returns with hundreds and even thousands of identified weak spots. However, it doesn’t tell which weak spot is severe enough to be a string that real hackers can pull to invade your environment. This is the main function of penetration testing.

Penetration testing does not just show you potential weak spots. It also gives you a frame of reference to treat as important the ones with the highest risk potential.

Conclusion

Modern-day organizations are dependent on technology more than ever before. This could have large-scale repercussions like loss of hugely sensitive data and millions of dollars in the event of a fortunate cyber invasion.

Penetration testing or pen testing, therefore, has a singular objective – to use an ethical hacker’s perspective for fishing out cyber vulnerabilities before a real-life, bad guy does. This allows security personnel to build strong defense systems and sabotage the efforts of any future possible hacks.