Cyber threats have dramatically escalated in recent years, with attackers continuously advancing tactics to infiltrate systems and steal data. Recent reports show that:
- Cyber crime costs the world over $6 trillion annually (Cybersecurity Ventures)
- A company is hacked every 39 seconds (University of Maryland)
- Over 80% of data breaches originate from application vulnerabilities (Forrester)
To defend against threats and avoid damages, organizations must validate security defenses before real attacks expose flaws in production environments. This proactive security assessment is known as penetration testing.
By safely attacking infrastructure, pen testing identifies vulnerabilities and quantifies risks so that technology leaders can strategically strengthen protections before disaster strikes. Let‘s explore what makes pen testing such an indispensable component of enterprise cyber resilience!
What is Penetration Testing?
Penetration testing, also called pen testing or ethical hacking, is the practice of launching authorized simulated cyber attacks against an organization‘s computer systems, networks, web apps, endpoints, cloud resources, wireless infrastructure, and more. It‘s all done in a controlled manner to evaluate security strengths and weaknesses.
Skilled pen testers think like real attackers, leveraging tools and techniques that emulate tactics used by hackers. The key difference is pen testers have explicit permission to probe environments. Actions are purely for defensive improvements rather than personal gain or harm.
Penetration testing provides enormous value:
Identifies Overlooked Weak Points
Pen testing often uncovers seemingly minor flaws that get deprioritized amid busy IT schedules. However, minor issues also represent the vulnerabilities most easily leveraged by hackers for major damage according to research from IBM, with basic misconfigurations frequently enabling initial access.
Proactively pen testing across your environment highlights these cracks that could become gaping holes when penetrated by intruders.
Validates Efficacy of Existing Defenses
While prevention via firewalls, endpoints, access controls, and other tools is important, detection and response mechanisms must also work when adversaries inevitably bypass the first line of defense.
Through simulated attacks, pen testing verifies that monitoring, alerting, and containment solutions all operate effectively to meet organizational incident response requirements.
Demonstrates Compliance
Most major regulations and standards like PCI DSS, HIPAA, SOC2, ISO 27001, and others explicitly mandate recurring penetration tests to verify security controls. Executive leadership can face steep fines and reputational damage for non-compliance.
Third-party penetration tests provide evidence to auditors that due care obligations are met, avoiding regulatory fines.
Enables Data-Driven Planning
Detailed post-assessment reports equip CISOs and technology steering committees with intimate awareness of specific vulnerabilities tied directly to business risks. These insights fuel data-driven prioritization and planning for security initiatives across people, process, and technology.
Strengthening defenses based on pen testing findings allows organizations to get the most bang for their security buck!
The Penetration Testing Process
While exact procedures vary, pen testing typically involves three main phases conducted in sequential order:
Reconnaissance
Effective military operations rely on accurate battlefield intelligence. Similarly, successful pen test campaigns are grounded in comprehensive reconnaissance activities early on.
The reconnaissance stage focuses on gathering information about the target environment, including details about:
- Network infrastructure
- Hosts and external facing assets
- Employees and related personas
- Active directories/access management controls
- Supply chain connections
- Physical locations
- And more…
Information is gathered from public sources like WHOIS records, job boards, social networks, and internet footprinting. Recon activities also interact directly with in-scope assets, whether through port scans, service enumeration, protocol detection, or other active discovery techniques.
Data aggregated during the reconnaissance phase spotlight weaknesses like outdated versions, default configurations, and exposed proprietary source code. This powers informed exploitation later on.
Valuable recon tools include FOCA, Maltego, SpiderFoot, Recon-ng, and others. Let‘s explore a sample workflow:
Skilled pen testers synthesize findings into an intricate map of the environment, which informs all subsequent activities.
Vulnerability Scanning
With target details compiled, pen testers shift focus to vulnerability scanning. The goal is pinpointing specific exploitable flaws across in-scope assets.
Dynamic and static testing tools like Nessus, OpenVAS, and Nexpose contain thousands of cutting-edge detection checks and exploit modules that automatically exercise systems to uncover risks like:
- Unpatched software vulnerabilities
- Default or weak passwords
- Misconfigurations
- Plaintext storage of private data
- Broken access controls
- much more…
An example report:
Vulnerability scan results further guide the penetration testers on entry points and pathways into insider access.
According to Gartner, vulnerability assessments should be performed at least quarterly, with monthly or bi-weekly better for high-risk environments.
Exploitation
Armed with intimate infrastructure knowledge and an indexed vulnerability catalog, pen testing enters the exploitation phase.
The goal is successfully achieving objectives like data extraction, service disruption, system corruption, or maintaining persistent access — all without permanently damaging assets. Access and actions should emulate realistic hacking campaigns.
Common exploitation vectors include:
Network Attacks
- Packet sniffing & decryption
- Service exploitation
- Protocol manipulation
- Traffic interception
Web Application Attacks
- Input injection attacks
- Authentication weaknesses
- Session flaws
- Access control issues
Social Engineering Attacks
- Phishing
- Tailgating
- Pretexting
- Baiting
And more…
Metasploit, sqlmap, and other tools facilitate exploitation, but custom coding and manual techniques crafted by seasoned pen testers uncover the most critical, specially-tailored flaws.
During exploitation, technical leads and executives receive periodic updates to stay abreast of scenarios emulating real attacker behaviors.
Reporting & Remediation Guidance
The culmination of penetration testing is a detailed report codifying findings, business impacts, and actionable remediation guidance:
Report Contents Checklist:
- Executive Summary
- Detailed technical findings
- Risk ratings aligned to impacts
- Proof-of-concept examples
- Specific remediation guidance
- Raw technical data as appendices
Armed with this information, organizational leadership can make data-driven decisions for security programs, infrastructure upgrades, and process enhancements. Fixing flaws is also vital — leaving holes unpatched based on pen test findings equates to willful negligence.
Post reporting, prioritize forming a collaborative remediation plan between security and IT teams. Measure progress towards hardening environments against additional attacks.
Who Should Leverage Penetration Testing?
Virtually all medium-to-large enterprises benefit from recurring penetration tests, especially companies:
- Handling sensitive customer data
- Operating consumer web applications
- Developing cutting-edge technologies
- Reliant on connected digital supply chains
- Undergoing cloud transformations
- And more…
For software companies, integrating pen testing into pre-launch quality assurance and continuous delivery workflows is a must. Rigorously pen testing applications, APIs, infrastructure-as-code templates and more before release prevents exponentially higher remediation costs later.
Fixing post-launch also means facing PR nightmares, damaged customer trust, compliance violations, lawsuits and more if flaws become breaches in production.
Additionally, heavily regulated industries like finance, healthcare, energy, and pharmaceuticals rely on penetration tests to satisfy auditors during compliance checks for standards like PCI DSS, HIPAA, NERC CIP, FDCC, FISMA, and others.
Third-party assessments demonstrate security due care, avoiding steep non-compliance fines.
Below are additional environments well-suited for routine penetration tests:
Now let‘s shift gears to concrete penetration testing best practices.
Best Practices for Maximum Impact
Properly scoping goals, hiring experienced ethical hackers, granting full access, and planning for findings are all crucial for successful security evaluations.
Here are 8 pen testing best practices:
1. Define Clear Goals
Document precise test objectives and desired outcomes focused on high-value targets, data types, compliance demands, and elevated risk areas.
Example goal: Validate multi-factor authentication mechanisms effectively contain access to patient health records if VPN gateway credentials are compromised.
Well-defined goals enable custom scenarios emulating real-world campaigns targeting what matters most.
2. Secure Leadership Buy-In
Conduct kickoff briefings with leadership teams to align expectations before testing begins through an approved Rules of Engagement (ROE).
Previewing upcoming simulated attacks prevents false alarms mid-test. The ROEs also grant legal permission to testers for all actions.
3. Hire Experienced, Ethical Hackers
Your pen testing team should be viewed as an extension of internal security – skilled, vetted, and trusted. Lean on offensive security veterans with backgrounds spanning red teaming, forensics, intelligence, cryptography, and more.
Combatting cutting-edge threat actors requires teams that think similarly.
4. Provide Full Environment Access
For comprehensive testing, temporary admin-level access matching real intruders must be granted across in-scope systems. Limiting access hides flaws rather than revealing them.
Pen testing reduced access equates to giving attackers a head start over your team.
5. Empower Thorough Testing
The most effective pen tests go far beyond simple vulnerability scans by assessing relationships between flaws for maximum impact. Guide testers to rigorously evaluate how weaknesses chain together.
Attackers won’t stop after easily grabbing low-hanging fruit!
6. Utilize Both In-House and External Teams
Third-party testers showcase unbiased perspectives – equally critical is growing internal red teams. Together, these forces strengthen defenses through diverse insights.
7. Plan Remediation Paths Upfront
Flaw remediation requires prioritization based on risks, available resources, budgets, and technical feasibility. Planning remediation processes beforehand ensures rapid response once testing concludes.
8. Initiate Repeated Testing Cycles
Schedule frequent recurring penetration tests on 6 or 12 month intervals to continually validate defenses against evolving attacker tradecraft leveraging bleeding-edge techniques.
Consistency is critical given regular changes in internal environments and the external threat landscape.
Integrating penetration testing best practices elevates prevention, detection, and response capabilities. Next let’s explore powerful pen testing tools.
Recommended Penetration Testing Tools
My top recommended pen testing tools include:
Network & Infrastructure
- Nmap – Powerful port scanner and service enumerator
- Metasploit – Exploitation framework filled with penetration modules
- tcpdump – Packet capture utility for network traffic analysis
- Cisco Global Exploiter – Targets default credentials on Cisco gear
Web Applications
- Burp Suite – Intercept traffic for manipulation and replay
- OWASP ZAP – Find web application vulnerabilities
- Nikto – Scan servers and apps for weak configurations
- sqlmap – Automate SQL injection discovery and exploitation
Mobile Applications
- apktool – Unpack and repackage Android apps to uncover flaws
- objection – Powerful runtime mobile exploration toolkit
- MobSF – Scan mobile apps for vulnerabilities and data leaks
- Frida – Dynamic instrumentation toolkit for reverse engineering mobile apps
Reporting & Remediation
- Faraday – Collaborative pentest reporting and tracking remediation
- Serpico – Guided reporting pipeline to build polished reports
- DefectDojo – Track vulnerability report metrics across tests
And more…
Choosing tools aligned to assessment goals and target environments streamlines testing and drives actionable findings.
As part of onboarding new tools, hands-on training is crucial to maximize value. Evaluate free trials and open-source options before purchasing licenses.
Conclusion & Next Steps
Regular penetration testing provides immense value for proactively securing systems and applications against continuously evolving real-world attacks. By safely identifying and fixing flaws before criminals discover them, organizations reduce business risk and avoid high-profile breaches.
Now you‘re equipped with comprehensive knowledge on exactly what penetration testing is, how ethical hacking assessments systematically uncover risks, when tests should be conducted, and tools to enable successful security evaluations.
To build a resilient cybersecurity posture on par with top enterprises, prioritize the following next steps:
1. Brief leadership on pen testing benefits and best practices
2. Issue an RFP for third-party pen testing services
3. Schedule recurring tests on a 6 or 12 month interval
4. Build an internal red team to scale testing velocity
5. Integrate pen testing into pre-launch QA and software development
6. Maintain and frequently re-assess a detailed remediation plan
7. Continuously tune environments leveraging latest findings
By consistently pen testing and remediating based on discoveries, your organization will sustain robust defenses, achieve compliance, and instill confidence across customers, partners, and employees.
To dive deeper, check out the following penetration testing resources:
- Penetration Testing Execution Standard (PTES)
- NIST SP 800-115 Technical Guide to Information Security Testing and Assessment
- Penetration Testing Framework 0.59
- Open Source Security Testing Methodology Manual (OSSTMM)
- Cloud Penetration Testing guide from INE
Ongoing penetration testing and remediation enable technology and InfoSec teams to collaboratively harden environments while sustainably advancing critical initiatives – the keys for simultaneously innovating while keeping threats at bay!
