Penetration Testing: The Good Kind of

pen testing cyber wise guy

Cybersecurity is about protecting computer systems, networks, software, and data from unauthorized access or attacks. It’s more important than ever in today’s digital world, as we all depend on technology and the internet for our daily tasks. With increasing cyber threats, good cybersecurity is crucial for keeping sensitive information, infrastructure, and assets safe from breaches.

  • Protecting privacy – Billions of individuals store personal and financial data online, which criminals seek to steal through malware, phishing scams, and hacking. Good cybersecurity helps safeguard sensitive user information.
  • Securing critical infrastructure – Modern infrastructure like power plants, transportation, and water systems rely on computer networks. Cyber attacks could disrupt essential services and endanger public safety. Cybersecurity reduces these risks.
  • Combating cybercrime – Cybercrime costs the global economy over $1 trillion annually. Effective cybersecurity deters criminals and mitigates attacks.
  • National security – Government systems contain highly confidential data. Weak cybersecurity exposes nations to espionage, loss of intellectual property, and acts of cyber warfare. Strong defenses enhance security.
  • Compliance – Industries like finance and healthcare have legal obligations to secure data. Cybersecurity helps meet compliance requirements.
  • Protecting trade secrets & IP – Companies invest in R&D and contain trade secrets. Cybersecurity protects proprietary information and intellectual property.
  • Maintaining public trust – Customers expect organizations to keep data safe. Good cybersecurity preserves an entity’s reputation.

Given what’s at stake, cybersecurity is very important in the digital world. Some key threats are malware, ransomware, phishing, DDoS attacks, insider threats, and others. Using strong defenses can help lower these risks.

Common Cyber Threats

Cyber threats come in many forms, but some of the most common and dangerous threats include:


Malware is bad software that can harm computers. It includes viruses, worms, Trojan horses, ransomware, spyware, and other harmful programs. Malware can delete files, lock users out of their devices, monitor activities, or steal sensitive information. It often spreads through fake emails, infected websites, or networks that have been attacked.


Phishing is when cybercriminals send fake emails or texts pretending to be trusted sources. They do this to trick people into sharing their login details or other important information. These messages usually have links to fake websites that steal data. Spear phishing targets specific individuals or organizations. Whaling phishing goes after high-profile executives.

Social Engineering

Social engineering is when bad actors trick people instead of directly attacking systems. They might pretend to be someone trusted, like IT support, to get passwords or access. This often involves phishing. Social engineering takes advantage of human traits like wanting to help, fear, or greed.

DDoS Attacks

A DDoS attack tries to make a system unavailable by flooding it with more traffic than it can handle. Attackers use infected devices to do this. As a result, websites and networks become inaccessible to real users.

Data Breaches

A data breach is when important or secret information is accessed without permission. Breaches usually happen because of security problems or mistakes in processes. They can reveal customer records, intellectual property, financial information, and more. Stopping breaches needs strong security measures and constant attention.

Penetration Testing Overview

Penetration testing, also known as pen testing or ethical hacking, means doing authorized practice cyberattacks on computer systems, applications, networks, or devices to check for security problems. The aim is to make the systems more secure by finding and fixing weaknesses before bad people can use them.

Penetration testing has several important benefits:

  • Finding vulnerabilities and security gaps: Pen tests probe systems in the same way real attackers would, uncovering vulnerabilities that may be missed by automated scans or compliance audits. This allows organizations to address issues before they lead to breaches.
  • Testing defenses: Penetration testing evaluates the effectiveness of existing security measures like firewalls, antivirus software, and access controls. It can reveal whether defenses are properly configured, up to date, and able to withstand attacks.
  • Raising security awareness: By experiencing simulated attacks, organizations gain a more thorough understanding of potential threats. Pen testing helps justify additional investments in security protections and training.
  • Compliance: Many industry regulations and standards require penetration testing on a regular basis. Banks, healthcare providers, government agencies, and other regulated industries use pen tests to satisfy compliance requirements.

Penetration tests are like practice for security. They use tools and methods similar to real attacks, but with rules and supervision. There are different types of pen tests that look at different security areas.

  • Network penetration testing evaluates the security of network infrastructure and devices like routers, firewalls, and switches.
  • Web application testing targets the web apps and APIs used by customers and employees.
  • Mobile app testing assesses the security of mobile apps.
  • Social engineering testing examines how staff respond to phishing, phone scams, and other deception tactics.
  • Physical penetration testing evaluates physical access controls to facilities, data centers, work areas, etc.

Overall, penetration testing helps organizations find and fix security weaknesses before hackers can exploit them. Regular pen tests are a good way to improve cybersecurity.

Planning a Pen Test

Penetration testing, also called pen testing or ethical hacking, is a authorized simulated cyberattack on a computer system to assess security. It’s important to plan properly for an effective pen test.

Determine Scope and Goals

First, decide what you want to achieve with the pen test. It could focus on a particular system, network, or application. Your goals might be finding weaknesses, understanding how attacks could affect you, or checking your internal security measures. Make sure your plans match your business goals.

Get Permission

Obtain approval from management before conducting tests. Clearly outline the scope, objectives, timeline, methods, and reporting. Legal permission safeguards the testers and ensures credibility.

Pick Testers

Select skilled internal IT staff and/or outside security consultants. Look for technical knowledge, good communication, and experience with penetration testing and ethical hacking. Utilize both internal and external testers for an inside-outside assessment.

Set Rules of Engagement

Define clear rules of engagement that testers must follow:

  • Which systems/networks/applications can and cannot be tested
  • What testing methods are allowed or prohibited
  • When testing can be performed
  • How far vulnerabilities can be exploited
  • Mandatory confidentiality of discovered vulnerabilities
  • How results should be documented and reported

Carefully crafted rules of engagement prevent undesirable impacts like system crashes.

With thoughtful planning and clear rules, a penetration test can effectively evaluate cyber defenses without disrupting operations.


Reconnaissance is the important first phase in penetration testing. Its aim is to gather as much information as possible about the target systems and environment before attempting intrusion or exploitation.

Some key reconnaissance activities include:

  • Identify systems and IP addresses: Pen testers will use various tools to map out the target’s network and identify live systems and their IP addresses. OS fingerprinting allows pen testers to identify operating systems running on discovered machines.
  • Find open ports and services: Port scans identify open ports on target systems which often reveal services running on the hosts. Common scanning tools include Nmap, Unicornscan, and Hping. Analyzing the open ports gives insight into potential vulnerabilities.
  • Discover user accounts: User enumeration allows gathering of usernames, email addresses, and other user account details. This reconnaissance can reveal weak or default passwords to target.
  • Identify vulnerabilities: Vulnerability scanners like Nessus, OpenVAS, and Nikto automate searching for known vulnerabilities such as missing patches or software flaws. Any findings provide pen testers potential options to gain access.
  • Gather public info: Pen testers will research the company, employees, and technologies online to gain additional intel. Useful public sources include DNS records, WHOIS data, LinkedIn profiles, website sources, job postings, etc.
  • Analyze metadata: Reviewing metadata in documents, images, and other files leaked online can reveal hidden information. Metadata often contains system properties, usernames, file paths, etc.

Thorough reconnaissance helps pen testers map the target environment and find the most promising vulnerabilities to focus on for exploitation. Planning and gathering information carefully set the foundation for a successful penetration test that adds value.


The scanning phase in a penetration test involves using tools to find and check the target systems and infrastructure for potential weaknesses that could be taken advantage of. The goal is to map out the attack surface and find weak points where attackers could get in.

During scanning, the tester will use tools like Nmap to see which ports are open on target systems. They will use Nessus to check services on open ports for any known weaknesses. Tools can also be used to find out the versions of services and applications running on the targets.

Knowing the exact versions is important, as it allows the tester to search for any known weaknesses and exploits that may work. Important information like operating system type and versions, along with application versions, can all be found during scanning.

Vulnerability scanning may reveal issues like outdated software, default or weak credentials, unpatched services, and misconfigured firewalls. All these could potentially provide a way into the network. The results of the scanning phase create a blueprint of the attack surface and help to identify possible weaknesses to be exploited in the next phase.

Using various scanning tools and techniques allows the tester to map out the target environment thoroughly. Checking for vulnerabilities provides important insights into weak points in the organization’s security. All of this preparation sets the penetration tester up for attempting exploitation in the next phase.


The exploitation phase is when pentesters try to use the weaknesses found during scanning to get more access to the target network. They want to get higher privileges, access restricted systems and data, and move through the network.

Some common exploitation techniques include:

  • Elevation of privilege – Exploiting vulnerabilities to gain administrator or root privileges on a system. This may allow installing backdoors, accessing restricted files, etc.
  • Remote code execution – Exploiting remote command execution flaws to execute arbitrary code and commands on the target. This can be used to drop malware, create new user accounts, etc.
  • Credential dumping – Using tools like Mimikatz to harvest account credentials from compromised systems. These credentials can then be used to expand access.
  • Password cracking – Cracking weak passwords obtained from password dumps to gain access to accounts. Rainbow tables and password cracking tools like John the Ripper are used.
  • SQL injection – Exploiting SQL injection flaws to read, modify, and extract data from databases. A pentester may be able to access sensitive data like customer records.
  • Privilege escalation – Vertical movement through a network by exploiting vulnerabilities to gain access to additional systems. For example, compromising a standard user account and then exploiting a separate flaw to gain administrator access.
  • Lateral movement – Horizontal movement through the network by exploiting vulnerabilities to gain access to additional systems at the same privilege level. For example, using pass-the-hash techniques to pivot from one system to another.

The exploitation phase is very important because it helps to find out how much access an attacker can get. Pentesters try to use all vulnerabilities to pretend the worst situations. This gives the client a clear idea of the risks.


After successfully hacking into a system, the penetration tester will want to keep access, collect usernames and passwords, and find important assets within the hacked network.

Keeping access is important so the tester can keep using any gains from the hack. This is often done by adding backdoors, rootkits, or other software that allows remote access even after a system is restarted. The goal is to have a way back into the network at any time.

Collecting usernames and passwords is also important, as most networks use centralized authentication systems. By getting this information, the tester can move to other systems using compromised accounts. Keylogging, memory scraping, and configuration file extraction are common ways to get usernames and passwords.

Lastly, finding important assets helps prioritize systems and data to take. The penetration tester will look for databases, file servers, source code repositories, and other valuable targets. Knowing where these assets are lets the tester take over the most important systems and applications.

Post-hack is the last stage of the test where the tester shows how much access could be gained. By keeping access, taking usernames and passwords, and finding important resources, the penetration tester shows weaknesses that could be used by real attackers.


Reporting after a cybersecurity test is crucial. The report should list all the findings and give advice on how to address the issues. It should be easy for everyone involved to understand. The aim is to help the organization enhance its security. A well-written report with helpful guidance can assist the organization in making wiser cybersecurity decisions.

Improving Cybersecurity

Cybersecurity needs to be constantly worked on, not just fixed once. After a penetration test, organizations should follow these key steps:

Implement Recommendations

The penetration testing report will contain a list of weaknesses found and suggestions on how to resolve them. Companies should focus on and put into action these suggestions promptly. Begin with the most serious and extremely severe discoveries. Creating a plan to fix the problems can make sure that all issues are dealt with gradually.

Patch Systems

One of the simplest but most important things organizations can do is make sure they are regularly updating their systems and software. Cyber criminals take advantage of known weaknesses that have fixes available. By using tools to manage and automatically install these fixes, organizations can enhance their security.

Train Employees

Employees can sometimes make mistakes that lead to cybersecurity problems. Hackers may trick them with social engineering and phishing. It’s important to regularly teach employees about security to help them understand cyber threats, promote a secure environment, and show them how to avoid incidents.

Harden Infrastructure

There are many things organizations can do to make their networks, servers, and other infrastructure more secure. For example, they can use multi-factor authentication, separate their networks, only allow approved applications, turn off unnecessary services and ports, encrypt their data, and use firewalls. When security is built into the infrastructure, it’s much more difficult for attackers to get in and move around.

Regularly testing for weaknesses and following recommendations to strengthen infrastructure helps organizations find and fix security problems before cyber criminals can take advantage of them. Staying watchful is important for good cybersecurity.