How to Perform a Penetration Test

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Reviewed by Cera Adams

Director, Assurance Services at OCD Tech

Updated Oct, 9

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Penetration testing is a controlled process where security experts simulate attacks on a system by planning, reconnoitering, scanning for vulnerabilities, exploiting them, and finally reporting their findings.

 

How to Perform a Penetration Test

 

A penetration test examines the security of a system by following well-defined stages. Below is an outline of these steps with simple explanations:

  • Planning and Preparation: Identify the target systems, define the scope (what parts to test), and set the rules of engagement to ensure the test is safe and legal. This phase establishes the objectives and limitations of the test.

  • Information Gathering (Reconnaissance): Collect public and accessible data about the target, such as IP addresses and open ports, without disturbing the system. Techniques like social engineering or passive data collection can also be used.

  • Scanning and Vulnerability Assessment: Use automated tools and manual testing to scan the system for vulnerabilities. This helps identify potential weaknesses (like outdated software or misconfigurations) that an attacker could exploit.

  • Exploitation: Attempt to exploit the identified vulnerabilities in a controlled manner to determine if unauthorized access or damage is possible. This step is carefully executed because its goal is to mimic an attack without causing harm.

  • Post-Exploitation and Analysis: Once a vulnerability is exploited, analyze what access was gained and how far an attacker could go. This helps determine the potential impact of an actual breach and informs ways to mitigate the risk.

  • Reporting: Document all findings, including the vulnerabilities discovered, the methods used, and recommendations for improvement. The report should be detailed enough for technical teams and clear enough for management.

Throughout the process, it’s essential to operate with clear objectives, maintain thorough documentation, and adhere to legal standards. If you ever need guidance in planning or reviewing your security strategies, our team at OCD Tech is experienced in consulting and readiness assessments.

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Frequently asked questions

What services does OCD Tech provide?

OCD Tech offers a comprehensive suite of cybersecurity and IT assurance services, including SOC 2/3 and SOC for Cybersecurity reporting, IT vulnerability and penetration testing, privileged access management, social engineering assessments, virtual CISO (vCISO) support, IT general controls audits, WISP development, and compliance assistance for frameworks like CMMC, DFARS, and FTC Safeguards.

Which industries does OCD Tech serve?

OCD Tech specializes in serving highly regulated sectors such as financial services, government, higher education, auto dealerships, enterprise organizations, and not-for-profits throughout New England.

How long does an IT security assessment take?

Typically, OCD Tech’s on-site work spans 1–2 days, depending on complexity and number of sites, followed by 1–2 weeks of analysis and reporting to deliver clear, actionable recommendations.

Why should I get SOC 2 compliant?

SOC 2 reporting demonstrates to clients and prospects that an organization follows best-in-class controls over security, availability, processing integrity, confidentiality, and privacy—boosting trust, meeting RFP/due diligence requirements, and helping secure contracts. OCD Tech helps organizations achieve and maintain this compliance.

Can OCD Tech help me with federal cybersecurity regulations?

Yes—OCD Tech provides guidance for compliance with DFARS (NIST 800‑171), CMMC (Levels 1–3), and FTC Safeguards, ensuring organizations meet specific government or industry-based cybersecurity mandates.

What is a virtual CISO (vCISO), and do I need one?

A virtual CISO delivers strategic, executive-level cybersecurity leadership as a service. OCD Tech’s vCISO service is ideal for organizations lacking a full-time CISO and helps build programs, define policy, oversee risk, and guide security maturity.

Does OCD Tech offer ongoing security training or audits for staff?

Absolutely. OCD Tech provides tailored internal IT Audit training and security awareness sessions, plus annual reviews of Written Information Security Programs (WISP), such as Massachusetts 201 CMR 17 and other state or industry-specific controls.

Audit. Security. Assurance.

IT Audit | Cybersecurity | IT Assurance | IT Security Consultants – OCD Tech is a technology consulting firm serving the IT security and consulting needs of businesses in Boston (MA), Braintree (MA) and across New England. We primarily serve Fortune 500 companies including auto dealers, financial institutions, higher education, government contractors, and not-for-profit organizations with SOC 2 reporting, CMMC readiness, IT Security Audits, Penetration Testing and Vulnerability Assessments. We also provide dark web monitoring, DFARS compliance, and IT general controls review.

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25 BHOP, Suite 407, Braintree MA, 02184

844-623-8324

https://ocd-tech.com

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