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Penetration Testing in 2025: Methods, Technologies & Practices
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What Is Penetration Testing?
Penetration testing, often called pentesting, is a simulated cyberattack on a computer system, network, or application to identify vulnerabilities. This process involves ethical hackers attempting to breach security defenses using various techniques and tools. The objective is to detect weaknesses before malicious entities can exploit them.
Organizations employ pentesters to ensure that their defenses can withstand real-world cyber threats. It is part of a proactive cybersecurity strategy. By conducting regular pentesting, organizations can improve their security measures, adapting to new threat landscapes and reinforcing their defenses against evolving cyber threats.
Another aspect of penetration testing is providing organizations with insights into their security posture. This involves generating reports detailing identified vulnerabilities, risk levels, and recommended remediation steps. Pentesting helps in finding existing vulnerabilities and assesses the effectiveness of security measures currently in place.
Types of Penetration Testing
Pentesting includes different techniques aimed at assessing various facets of an organization’s security framework.
External Testing
External penetration testing focuses on identifying and exploiting vulnerabilities in an organization’s internet-facing assets. These may include web servers, mail servers, VPN gateways, and domain name system (DNS) services. The test simulates an attacker with no internal access, replicating threats from hackers operating over the internet.
Testers begin with reconnaissance, mapping out the target's digital footprint using tools to identify open ports, services, and software versions. They then exploit known vulnerabilities, weak configurations, or mismanaged services. Findings from external tests help prioritize patching and improve firewall configurations, intrusion detection systems, and endpoint defenses.
Internal Testing
Internal testing simulates attacks from within the organization’s network perimeter. It reflects scenarios such as a disgruntled employee, a compromised internal account, or a malicious actor who has breached external defenses. The tester typically has some level of access, like a standard user or guest, and attempts to escalate privileges or access sensitive data.
This type of testing reveals the damage an insider or internal breach could cause. It evaluates internal controls, such as segmentation between departments, restrictions on access to sensitive systems, and logging of suspicious behavior. Internal pentests often uncover overlooked weaknesses, such as misconfigured user permissions, excessive trust between systems, or lack of monitoring.
Web Application Testing
Web application testing has a more limited scope than traditional penetration testing. It examines the security of software systems accessible through web browsers. This includes online banking platforms, e-commerce sites, and internal web portals. The test focuses on vulnerabilities defined in the OWASP Top 10, such as SQL injection, cross-site scripting (XSS), cross-site request forgery (CSRF), and broken authentication.
Testers use a mix of automated scanning and manual testing to explore how input is handled, how sessions are managed, and whether data is properly protected. They simulate attacker behavior to see if unauthorized actions can be performed, such as accessing another user's account or bypassing business logic.
Learn more in our detailed guide to web application penetration testing.
Wireless Testing
Wireless testing targets the security of wireless networks and devices, including corporate Wi-Fi, employee laptops, mobile devices, and internet of things (IoT) equipment. It evaluates access controls, encryption protocols (like WPA2 or WPA3), and network segmentation.
Testers attempt to intercept traffic, break encryption, create rogue access points, or impersonate legitimate devices. They also assess how well the network defends against unauthorized connections and data leakage.
Social Engineering Tests
Social engineering tests explore the human element of security by attempting to deceive or manipulate individuals into revealing sensitive information or performing unsafe actions. Common methods include phishing emails, phone pretexting, baiting with infected USB drives, or impersonation during in-person interactions.
These tests measure how well employees recognize and respond to manipulation attempts. They often reveal gaps in training, poor security awareness, or lack of verification procedures.
Physical Penetration Testing
Physical penetration testing assesses the effectiveness of physical security controls. Testers attempt to bypass locks, security guards, and surveillance systems to enter restricted areas or access sensitive equipment like servers or network switches.
Scenarios might involve entering into a facility using fake badges, accessing offices after hours, or planting unauthorized devices. This testing helps evaluate real-world vulnerabilities in physical access controls and how well staff enforce security protocols.
Penetration Testing vs. Red Teaming
While penetration testing and red teaming both evaluate an organization’s security, they differ in scope, objectives, and methodology.
Penetration testing is goal-oriented and scoped to identify and exploit known vulnerabilities in systems, applications, or network segments. It is often time-boxed and focused on breadth over stealth. Pentesters usually operate with some degree of transparency and communicate findings promptly.
Red teaming simulates a full-scale, multi-vector attack mimicking a real adversary. It emphasizes stealth, persistence, and lateral movement to test detection and response capabilities. Red teams do not restrict themselves to predefined targets—they may combine cyber, physical, and social engineering techniques to achieve objectives, such as data exfiltration or domain compromise, often without the defenders’ knowledge.
Phases of a Successful Pen Test
Penetration testing is structured into several phases to methodically uncover and assess vulnerabilities.
1. Scoping
Scoping defines the rules, objectives, and boundaries of a penetration test. This phase ensures alignment between the testing team and the organization on what will be tested, how, and to what extent. It includes identifying in-scope assets such as IP addresses, applications, and facilities, and specifying exclusions to prevent unintended disruptions.
Testers gather technical and business context to understand the environment and identify systems that could impact the organization’s operations. Legal and compliance considerations are addressed, and permissions are documented to authorize testing activities. A well-defined scope prevents ambiguity, limits legal risk, and ensures that the test delivers useful, targeted results.
2. Reconnaissance
Reconnaissance, or information gathering, involves collecting as much data as possible about the target systems, networks, and personnel. This phase helps testers map the attack surface and plan their approach by identifying potential weak points.
There are two types of reconnaissance: passive and active. Passive reconnaissance involves indirect methods like analyzing public data, WHOIS records, DNS information, and employee social media profiles. Active reconnaissance engages with the target directly—ping sweeps, port scanning, or service enumeration—to gather technical information. The goal is to compile a detailed profile of the target to inform the scanning and exploitation phases.
3. Scanning and Vulnerability Identification
In this phase, testers perform detailed scans of the target environment using tools like Nmap, Nessus, or Burp Suite. The objective is to identify open ports, active services, system banners, and software versions. Testers analyze this data to detect known vulnerabilities and misconfigurations.
Scanning is often automated, but manual validation is critical to eliminate false positives. Vulnerability databases, such as CVE and NVD, help map discovered services to potential weaknesses. This step builds a prioritized list of exploitable targets, guiding the next phase of attack simulation.
Learn more in our detailed guide to vulnerability assessment.
4. Exploitation and Privilege Escalation
Once vulnerabilities are identified, testers attempt to exploit them to gain unauthorized access. Exploits may target web applications, network services, or system misconfigurations. This phase confirms the real-world risk posed by the vulnerabilities, distinguishing theoretical risks from practical ones.
After initial access, testers try to escalate privileges to move from limited user roles to administrative or root-level access. This is achieved by exploiting local flaws, such as weak permissions, unpatched kernel vulnerabilities, or credential reuse. The goal is to demonstrate the impact of a breach—whether data can be exfiltrated, systems can be controlled, or further internal movement is possible.
5. Post-Exploitation and Reporting
Post-exploitation involves maintaining access, assessing the value of compromised assets, and evaluating lateral movement opportunities. Testers explore the extent of control they can establish, such as accessing databases, emails, or internal tools. They also check if activities were logged or detected, giving insights into the organization’s monitoring and response capabilities.
Finally, the results are compiled into a detailed report. This includes exploited vulnerabilities, attack paths, risk levels, and recommendations for remediation. Reports often separate technical findings from executive summaries, enabling both technical teams and decision-makers to take informed actions.
Tips from the Expert
Dima Potekhin
CTO and Co-Founder
Dima Potekhin, CTO and Co-Founder of CyCognito, is an expert in mass-scale data analysis and security. He is an autodidact who has been coding since the age of nine and holds four patents that include processes for large content delivery networks (CDNs) and internet-scale infrastructure.
In my experience, here are tips that can help you better strengthen your penetration testing program beyond what’s already covered:
- Perform threat modeling before the test begins: Align the pentest with realistic threat scenarios based on adversary TTPs (tactics, techniques, and procedures) targeting the industry. Use frameworks like MITRE ATT&CK to define attacker profiles and ensure testing simulates the most relevant threats to the organization.
- Use “assumed breach” scenarios in internal tests: Go beyond initial access—start internal tests with assumed access (e.g., a compromised workstation or domain user) and focus efforts on lateral movement, privilege escalation, and data exfiltration. This gives insight into actual blast radius if external defenses fail.
- Test cloud misconfigurations with provider-specific tools: Don’t rely solely on generic pentest tools—use CSP-specific tools (like Prowler for AWS and ScoutSuite for Azure/GCP) to detect permission flaws, overly permissive IAM roles, or insecure storage buckets. Cloud misconfigurations are often missed in traditional tests.
- Apply evasion techniques to assess detection capabilities: Test the blue team by using payload obfuscation, encoding, and C2 (command-and-control) traffic mimicry. Evaluate how well EDR/XDR platforms and SIEM rules detect obfuscated exploits, PowerShell abuse, or living-off-the-land binaries (LOLBins).
- Correlate test results with business impact mapping: Don’t just list vulnerabilities—map each exploited path to actual business assets (e.g., revenue systems, PII databases). This prioritizes remediation based on what matters most and helps justify security investment to leadership.
CyCognito White Paper
Rethinking Penetration Testing
Your pen testing team is working hard, but they are facing an operational challenge due to the large number of assets they need to test and the time required to complete each test.
Download this white paper to uncover the challenges with pen testing in reducing external risk, how automation can help pen testers and red teams work more efficiently, and how CyCognito can add value.
How Much Does a Penetration Test Cost?
Below are approximate cost ranges for different types of penetration testing. These figures are general estimates; actual costs can vary based on project requirements.
- Network penetration testing: Typically ranges from $5,000 to $25,000, depending on the complexity of the network.
- Web application penetration testing: Costs range approximately from $5,000 to $30,000 per application, depending on complexity of the application and the depth of testing required.
- Mobile application penetration testing: Typically ranges from $7,000 to $35,000 per application, mainly depending on complexity of the app and number of platforms tested.
- Cloud service penetration testing: Costs typically range from $10,000 to $50,000, depending on the complexity of the cloud architecture, number of services tested, and compliance requirements.
- API penetration testing: Costs range approximately from $5,000 to $25,000 per API, depending on the number and complexity of endpoints assessed and integration effort.
Key cost drivers include:
- Scope: Number of systems, applications, or locations in scope.
- Testing type: Web app, wireless, internal, external, or full-scope.
- Depth: Time-boxed vs. objective-based testing, duration of test, and thoroughness required.
- Compliance requirements: PCI DSS, HIPAA, or ISO standards may require specific testing methodologies and documentation.
Learn more in our detailed guide to penetration testing costs.
Key Types of Pentesting Solutions
With varying needs and resources, organizations can choose from different pentesting solutions to secure their systems.
Manual Penetration Testing
Manual penetration testing is conducted by professional ethical hackers who simulate real-world attacks using a combination of technical knowledge, creativity, and experience. This method is especially effective for identifying complex vulnerabilities that automated tools often miss, such as business logic flaws, privilege escalation paths, and chained attack vectors. Manual testing provides depth and context that tools can’t replicate.
It's commonly used in high-stakes environments where accuracy and thoroughness are critical—such as financial systems, healthcare applications, or environments requiring compliance with strict security standards. While manual testing is more time-consuming and costly, it produces high-quality insights that can guide meaningful security improvements.
Automated Penetration Testing Tools (AutoPT)
Automated pentesting tools (AutoPT) use predefined rules and vulnerability databases to scan systems, networks, or applications. These tools are used to quickly identify common security issues such as outdated software, weak configurations, and known exploits. They are well-suited for initial assessments, regular compliance checks, and vulnerability management programs.
Automation allows for rapid coverage of large environments, saving time and reducing human error in repetitive tasks. However, these tools can generate false positives or miss context-specific or logic-based vulnerabilities. As such, automated testing is best used in combination with manual validation to ensure accuracy and completeness.
Cloud-Based Penetration Testing Platforms (PTaaS)
Penetration Testing as a Service (PTaaS) platforms provide a scalable, on-demand testing model delivered through a cloud interface. These platforms offer continuous access to test results, remediation tracking, and communication with testing teams. PTaaS solutions often blend automated scanning with manual testing to support both speed and depth.
PTaaS is particularly useful for organizations operating in agile or DevOps environments where frequent testing is required. It enables integration into development pipelines and offers visibility to both technical teams and management through centralized dashboards.
Crowd-Sourced Penetration Testing (Bug Bounty Programs)
Bug bounty programs invite a global community of independent security researchers to discover and report vulnerabilities in exchange for rewards. Crowd-sourced platforms manage the logistics, including researcher vetting, scope enforcement, and payment handling. This model offers diverse testing techniques and real-world attacker perspectives, increasing the chances of uncovering rare or advanced vulnerabilities.
Crowd-sourced testing can be highly effective for public-facing systems and mature security teams. However, managing a bug bounty program requires clear scope definitions, effective triage processes, and internal resources to validate and respond to reports.
Key Penetration Testing Methodologies and Standards
Standardized methodologies guide penetration testing processes, ensuring consistency and thoroughness in identifying vulnerabilities. These frameworks offer structured approaches for planning and executing tests.
Open Source Security Testing Methodology Manual (OSSTMM)
Open Source Security Testing Methodology Manual (OSSTMM), developed by the Institute for Security and Open Methodologies (ISECOM), provides a framework for testing operational security. It emphasizes measurable results and focuses on five key channels: human, physical, wireless, telecommunications, and data networks. Unlike vulnerability-centered methods, OSSTMM evaluates how well controls protect assets under real-world operational conditions.
The methodology promotes unbiased testing by avoiding assumptions about system behavior or threat models. Testers quantify security through metrics like the "Security Test Audit Report" and "Operational Security Metrics," enabling organizations to benchmark and track improvements over time.
Penetration Testing Execution Standard (PTES)
Penetration Testing Execution Standard (PTES) outlines a process for conducting penetration tests across various environments. It includes seven stages: pre-engagement interactions, intelligence gathering, threat modeling, vulnerability analysis, exploitation, post-exploitation, and reporting. This structure ensures a consistent and repeatable testing process.
PTES also provides guidance on technical and non-technical aspects of a test, such as rules of engagement, legal considerations, and communication protocols. It's useful for teams seeking to align their testing with industry-recognized best practices, or for organizations hiring third-party testers and needing a clear framework for evaluating service quality.
OWASP Web Security Testing Guide (WSTG)
The OWASP Web Security Testing Guide (WSTG) is a framework for testing the security of web applications. It defines a broad set of test cases based on the OWASP Top 10 and covers areas like authentication, session management, input validation, and business logic flaws.
WSTG provides detailed checklists and testing procedures, allowing testers to assess both technical vulnerabilities and application-specific risks. It's widely adopted for securing applications that process sensitive data or support critical business functions. The guide also aligns with secure development practices, making it useful for integrating security into software development life cycles (SDLC).
NIST Special Publication 800-115
NIST SP 800-115, titled "Technical Guide to Information Security Testing and Assessment," is a U.S. government publication that offers a structured approach to security testing. It outlines techniques such as vulnerability scanning, penetration testing, security assessment, and security audits.
The guide helps organizations plan, execute, and evaluate tests based on risk management principles. It emphasizes pre-test planning, objective-based testing, and proper documentation. SP 800-115 is particularly relevant for federal agencies and organizations that must comply with U.S. cybersecurity standards.
Best Practices for Effective Pentesting
Effective penetration testing adheres to best practices ensuring comprehensive assessment and actionable insights. These practices optimize the testing process and improve security outcomes.
1. Clearly Define Scope and Objectives
Start by specifying which systems, networks, applications, or facilities are in scope. This includes IP ranges, domain names, cloud services, or internal environments. Equally important is identifying out-of-scope areas to avoid unintended disruptions. Objectives should clarify whether the test aims to assess regulatory compliance, detect exploitable flaws, or measure incident response readiness.
Defining scope also helps with legal protection by outlining acceptable testing boundaries and obtaining necessary approvals. Clear objectives guide the testing methodology, influence the choice of tools, and ensure that the results are aligned with business goals and risk management priorities.
2. Combine Manual and Automated Techniques
Automated tools are essential for identifying known vulnerabilities at scale. They rapidly scan for misconfigurations, outdated software, and exposed services using signature-based detection. However, they often lack the ability to interpret application logic or detect subtle security flaws.
Manual testing complements automation by simulating how real attackers chain vulnerabilities, exploit logic errors, or bypass controls through unconventional means. Techniques like fuzzing, code review, and custom payload crafting uncover deeper issues that automation overlooks. A hybrid approach ensures both breadth and depth in security testing.
3. Include Social Engineering Scenarios
Human factors are often the weakest link in security. Social engineering tests simulate real-world deception tactics such as phishing emails with malicious links, phone calls impersonating IT staff, or leaving infected USB drives in accessible areas. These tests help measure the resilience of employees and the organization’s ability to detect and respond to such threats.
Incorporating social engineering identifies training gaps and weaknesses in authentication or verification processes. It also allows organizations to reinforce incident response protocols and develop user awareness campaigns based on observed behaviors.
4. Conduct Ongoing Tests for Continuous Security
Cybersecurity is not static. New vulnerabilities emerge daily, systems are frequently updated, and attackers evolve their methods. Regular penetration testing helps organizations stay ahead of threats.
For agile environments, integrating testing into CI/CD pipelines ensures that vulnerabilities are caught early in development. Continuous testing through PTaaS platforms or crowdsourced services helps maintain security as an ongoing process.
5. Document Detailed Findings and Action Steps
A good penetration test is only as valuable as its documentation. Reports should categorize findings by severity (e.g., critical, high, medium, low) and include proof-of-concept details, affected systems, reproduction steps, and impact analysis. Screenshots, logs, and payloads help technical teams verify and resolve issues.
Actionable recommendations should prioritize fixes based on business risk and ease of remediation. A well-structured report should include an executive summary for decision-makers, technical details for IT staff, and a remediation tracker for follow-up. Proper documentation enables accountability, supports audits, and ensures that vulnerabilities are properly addressed.
Automated Penetration Testing with CyCognito
CyCognito built its external attack surface management (EASM) and security testing platform to replicate an attacker’s thought processes and workflows.
CyCognito automates the first phase of offensive cyber operation with deep reconnaissance and active security testing. Pen testing and red teaming staff are able to immediately focus on meaningful activities that require human decision.
With CyCognito, your teams have access to:
- Continuously updated reconnaissance information – Dynamic updates to your full asset inventory across all business divisions and brands – seed information and manual updates are not required.
- Automatic black box penetration test results – Over 30,000 penetration testing modules applied to full inventory of exposed network infrastructure and web applications.
- Integrated threat intelligence and remediation planning services – Guidance on which assets to test first, with evidence.
- Workflows built for collaboration – Create subteams dedicated to specific pen testing and red team staff. Organizations and assets can be assigned per team based on predefined scopes. Instant access to what to test next.
With CyCognito your offensive security teams can pivot faster to human-led exploitation-based tests:
- Reduce time consuming and tedious reconnaissance work
- Reach your ideal security testing goals
- Reduce burnout and get better results
- Get more ROI out of bug bounty programs
Learn more about CyCognito automated security testing.
CyCognito White Paper
Rethinking Penetration Testing
Your pen testing team is working hard, but they are facing an operational challenge due to the large number of assets they need to test and the time required to complete each test.
Download this white paper to uncover the challenges with pen testing in reducing external risk, how automation can help pen testers and red teams work more efficiently, and how CyCognito can add value.
Complimentary White Paper