147 In-Depth Penetration Testing Questions for Professionals

What is involved in Penetration Testing

Find out what the related areas are that Penetration Testing connects with, associates with, correlates with or affects, and which require thought, deliberation, analysis, review and discussion. This unique checklist stands out in a sense that it is not per-se designed to give answers, but to engage the reader and lay out a Penetration Testing thinking-frame.

How far is your company on its Penetration Testing journey?

Take this short survey to gauge your organization’s progress toward Penetration Testing leadership. Learn your strongest and weakest areas, and what you can do now to create a strategy that delivers results.

To address the criteria in this checklist for your organization, extensive selected resources are provided for sources of further research and information.

Start the Checklist

Below you will find a quick checklist designed to help you think about which Penetration Testing related domains to cover and 147 essential critical questions to check off in that domain.

The following domains are covered:

Penetration Testing, Penetration test, Amazon Standard Identification Number, Arch Linux, BlackArch Linux, Black box, Burp Suite, CBS Interactive, Commercial software, Free software, Gentoo Linux, IT risk, Information technology security audit, Massachusetts Institute of Technology, Metasploit Project, National Security Agency, OWASP ZAP, Parrot Security OS, Payment Card Industry Data Security Standard, RAND Corporation, Risk assessment, SANS Institute, Software system, Standard penetration test, System Development Corporation, Systems analysis, Tiger team, Tiger teams, United States Department of Defense, White box:

Penetration Testing Critical Criteria:

Guide Penetration Testing leadership and grade techniques for implementing Penetration Testing controls.

– What tools do you use once you have decided on a Penetration Testing strategy and more importantly how do you choose?

– What is the purpose of Penetration Testing in relation to the mission?

– Who sets the Penetration Testing standards?

Penetration test Critical Criteria:

Shape Penetration test tactics and devise Penetration test key steps.

– Is a vulnerability scan or penetration test performed on all internet-facing applications and systems before they go into production?

– Who will be responsible for deciding whether Penetration Testing goes ahead or not after the initial investigations?

– When a Penetration Testing manager recognizes a problem, what options are available?

– Who will provide the final approval of Penetration Testing deliverables?

Amazon Standard Identification Number Critical Criteria:

Scan Amazon Standard Identification Number leadership and devote time assessing Amazon Standard Identification Number and its risk.

– Who is the main stakeholder, with ultimate responsibility for driving Penetration Testing forward?

– How important is Penetration Testing to the user organizations mission?

– How much does Penetration Testing help?

Arch Linux Critical Criteria:

Substantiate Arch Linux visions and ask questions.

– Think about the kind of project structure that would be appropriate for your Penetration Testing project. should it be formal and complex, or can it be less formal and relatively simple?

– How can you negotiate Penetration Testing successfully with a stubborn boss, an irate client, or a deceitful coworker?

– Who are the people involved in developing and implementing Penetration Testing?

BlackArch Linux Critical Criteria:

Frame BlackArch Linux issues and achieve a single BlackArch Linux view and bringing data together.

– How do we make it meaningful in connecting Penetration Testing with what users do day-to-day?

– Do you monitor the effectiveness of your Penetration Testing activities?

– Why are Penetration Testing skills important?

Black box Critical Criteria:

Pilot Black box failures and proactively manage Black box risks.

– Who is responsible for ensuring appropriate resources (time, people and money) are allocated to Penetration Testing?

– How do we Improve Penetration Testing service perception, and satisfaction?

– Are there Penetration Testing problems defined?

Burp Suite Critical Criteria:

Pay attention to Burp Suite tactics and budget the knowledge transfer for any interested in Burp Suite.

– Marketing budgets are tighter, consumers are more skeptical, and social media has changed forever the way we talk about Penetration Testing. How do we gain traction?

– Are there any disadvantages to implementing Penetration Testing? There might be some that are less obvious?

– Which individuals, teams or departments will be involved in Penetration Testing?

CBS Interactive Critical Criteria:

Refer to CBS Interactive issues and balance specific methods for improving CBS Interactive results.

– What are your results for key measures or indicators of the accomplishment of your Penetration Testing strategy and action plans, including building and strengthening core competencies?

– What sources do you use to gather information for a Penetration Testing study?

– What are internal and external Penetration Testing relations?

Commercial software Critical Criteria:

Distinguish Commercial software tactics and mentor Commercial software customer orientation.

– How do you incorporate cycle time, productivity, cost control, and other efficiency and effectiveness factors into these Penetration Testing processes?

– Does Penetration Testing create potential expectations in other areas that need to be recognized and considered?

– Is maximizing Penetration Testing protection the same as minimizing Penetration Testing loss?

Free software Critical Criteria:

Co-operate on Free software adoptions and ask questions.

– How do you determine the key elements that affect Penetration Testing workforce satisfaction? how are these elements determined for different workforce groups and segments?

– Do the Penetration Testing decisions we make today help people and the planet tomorrow?

– Are we Assessing Penetration Testing and Risk?

Gentoo Linux Critical Criteria:

Check Gentoo Linux results and look at it backwards.

– What new services of functionality will be implemented next with Penetration Testing ?

– Risk factors: what are the characteristics of Penetration Testing that make it risky?

– Is Penetration Testing dependent on the successful delivery of a current project?

IT risk Critical Criteria:

Canvass IT risk tasks and diversify by understanding risks and leveraging IT risk.

– Does your company have defined information technology risk performance metrics that are monitored and reported to management on a regular basis?

– To what extent is the companys common control library utilized in implementing or re-engineering processes to align risk with control?

– To what extent is your companys approach to ITRM aligned with the ERM strategies and frameworks?

– What is the effect on the organizations mission if the system or information is not reliable?

– Does Senior Management take action to address IT risk indicators identified and reported?

– What best describes your establishment of a common process, risk and control library?

– How does your company report on its information and technology risk assessment?

– What information (both incoming and outgoing) is required by the organization?

– Does the IT Risk Management framework align to a three lines of defense model?

– How secure -well protected against potential risks is the information system ?

– How can organizations advance from good IT Risk Management practice to great?

– How can our organization build its capabilities for IT Risk Management?

– To what extent are you involved in IT Risk Management at your company?

– What is the sensitivity (or classification) level of the information?

– How often are information and technology risk assessments performed?

– Do you actively monitor regulatory changes for the impact of ITRM?

– Methodology: How will risk management be performed on projects?

– Does the board have a conflict of interest policy?

– How does your company report on its IT risk?

– How do you demonstrate due care?

Information technology security audit Critical Criteria:

Adapt Information technology security audit risks and budget for Information technology security audit challenges.

– At what point will vulnerability assessments be performed once Penetration Testing is put into production (e.g., ongoing Risk Management after implementation)?

– What is the source of the strategies for Penetration Testing strengthening and reform?

– Meeting the challenge: are missed Penetration Testing opportunities costing us money?

Massachusetts Institute of Technology Critical Criteria:

Familiarize yourself with Massachusetts Institute of Technology strategies and find out.

– How do your measurements capture actionable Penetration Testing information for use in exceeding your customers expectations and securing your customers engagement?

Metasploit Project Critical Criteria:

Grasp Metasploit Project adoptions and assess what counts with Metasploit Project that we are not counting.

– How can we incorporate support to ensure safe and effective use of Penetration Testing into the services that we provide?

– Is there a Penetration Testing Communication plan covering who needs to get what information when?

– What are all of our Penetration Testing domains and what do they do?

National Security Agency Critical Criteria:

Transcribe National Security Agency visions and finalize specific methods for National Security Agency acceptance.

– Do we aggressively reward and promote the people who have the biggest impact on creating excellent Penetration Testing services/products?

– Why should we adopt a Penetration Testing framework?

OWASP ZAP Critical Criteria:

Mix OWASP ZAP risks and grade techniques for implementing OWASP ZAP controls.

– How likely is the current Penetration Testing plan to come in on schedule or on budget?

– Think of your Penetration Testing project. what are the main functions?

– Do we have past Penetration Testing Successes?

Parrot Security OS Critical Criteria:

Consider Parrot Security OS risks and point out improvements in Parrot Security OS.

– Does Penetration Testing systematically track and analyze outcomes for accountability and quality improvement?

– How do mission and objectives affect the Penetration Testing processes of our organization?

– What are our Penetration Testing Processes?

Payment Card Industry Data Security Standard Critical Criteria:

Generalize Payment Card Industry Data Security Standard strategies and find the ideas you already have.

– Do those selected for the Penetration Testing team have a good general understanding of what Penetration Testing is all about?

– How do we keep improving Penetration Testing?

RAND Corporation Critical Criteria:

Examine RAND Corporation tasks and integrate design thinking in RAND Corporation innovation.

– Think about the functions involved in your Penetration Testing project. what processes flow from these functions?

– Are accountability and ownership for Penetration Testing clearly defined?

– Do we all define Penetration Testing in the same way?

Risk assessment Critical Criteria:

Face Risk assessment failures and find out what it really means.

– Have the it security cost for the any investment/project been integrated in to the overall cost including (c&a/re-accreditation, system security plan, risk assessment, privacy impact assessment, configuration/patch management, security control testing and evaluation, and contingency planning/testing)?

– Record-keeping requirements flow from the records needed as inputs, outputs, controls and for transformation of a Penetration Testing process. ask yourself: are the records needed as inputs to the Penetration Testing process available?

– Are interdependent service providers (for example, fuel suppliers, telecommunications providers, meter data processors) included in risk assessments?

– Does the risk assessment approach helps to develop the criteria for accepting risks and identify the acceptable level risk?

– Are standards for risk assessment methodology established, so risk information can be compared across entities?

– What core IT system are you using?  Does it have an ERM or risk assessment module; and if so, have you used it?

– Are standards for risk assessment methodology established, so risk information can be compared across entities?

– How frequently, if at all, do we conduct a business impact analysis (bia) and risk assessment (ra)?

– Does the process include a BIA, risk assessments, Risk Management, and risk monitoring and testing?

– Is the priority of the preventive action determined based on the results of the risk assessment?

– Do you use any homegrown IT system for ERM or risk assessments?

– How are risk assessment and audit results communicated to executives?

– Are regular risk assessments executed across all entities?

– Do you use any homegrown IT system for ERM or risk assessments?

– Are regular risk assessments executed across all entities?

– What triggers a risk assessment?

SANS Institute Critical Criteria:

Categorize SANS Institute decisions and simulate teachings and consultations on quality process improvement of SANS Institute.

– Is a Penetration Testing Team Work effort in place?

– How do we maintain Penetration Testings Integrity?

– What are current Penetration Testing Paradigms?

Software system Critical Criteria:

Recall Software system governance and perfect Software system conflict management.

– Imagine a scenario where you engage a software group to build a critical software system. Do you think you could provide every last detail the developers need to know right off the bat?

– Does the software system satisfy the expectations of the user?

– What does it mean to develop a quality software system?

– Is the software system functionally adequate?

– What about Penetration Testing Analysis of results?

– Is the software system productive?

– Is the software system effective?

– Is the software system efficient?

– Is the software system reliable?

– Is the software system usable?

– Is the software system safe?

Standard penetration test Critical Criteria:

Look at Standard penetration test governance and define Standard penetration test competency-based leadership.

– What management system can we use to leverage the Penetration Testing experience, ideas, and concerns of the people closest to the work to be done?

– What are our needs in relation to Penetration Testing skills, labor, equipment, and markets?

System Development Corporation Critical Criteria:

Merge System Development Corporation decisions and spearhead techniques for implementing System Development Corporation.

– What is the total cost related to deploying Penetration Testing, including any consulting or professional services?

– What are the Essentials of Internal Penetration Testing Management?

Systems analysis Critical Criteria:

Scan Systems analysis projects and frame using storytelling to create more compelling Systems analysis projects.

– How can expected costs and benefits be quantified to determine whether the new system will indeed be cost-effective?

–  What is the purpose of the Systems Analysis report during the Systems Analysis phase?

– How should one include criteria of equity and efficiency in performance assessment?

– What are the principal mechanisms likely to bring about performance improvements?

– What process must the company go through to obtain and implement a new system?

– What service providers would be able to build this application if outsourced?

– What is the purpose of splitting design into two parts: systems and detail?

– Operational feasibility. will the solution fulfill the users requirements?

– What types of planning are necessary to ensure the system s success?

– What are the organizations relationships with other organizations?

– How should Systems Analysis incorporate multisectoral components?

– How do we practically monitor or measure margin to criticality?

– On what basis would you decide to redesign a business process?

– Is this an acceptable application of a disruptive technology?

– Why is planning an important step in systems development?

– What types of systems development plans are needed?

– How will employees react to a new system?

– Systems Analysis and design: where is it?

– How broad should the analysis be?

– Can something be combined?

Tiger team Critical Criteria:

Analyze Tiger team strategies and proactively manage Tiger team risks.

– Can Management personnel recognize the monetary benefit of Penetration Testing?

Tiger teams Critical Criteria:

Exchange ideas about Tiger teams outcomes and define what do we need to start doing with Tiger teams.

– Are assumptions made in Penetration Testing stated explicitly?

– What are the business goals Penetration Testing is aiming to achieve?

United States Department of Defense Critical Criteria:

Nurse United States Department of Defense outcomes and arbitrate United States Department of Defense techniques that enhance teamwork and productivity.

– What role does communication play in the success or failure of a Penetration Testing project?

– Can we do Penetration Testing without complex (expensive) analysis?

– Does the Penetration Testing task fit the clients priorities?

White box Critical Criteria:

Recall White box projects and get answers.


This quick readiness checklist is a selected resource to help you move forward. Learn more about how to achieve comprehensive insights with the Penetration Testing Self Assessment:


Author: Gerard Blokdijk

CEO at The Art of Service | theartofservice.com



Gerard is the CEO at The Art of Service. He has been providing information technology insights, talks, tools and products to organizations in a wide range of industries for over 25 years. Gerard is a widely recognized and respected information expert. Gerard founded The Art of Service consulting business in 2000. Gerard has authored numerous published books to date.

External links:

To address the criteria in this checklist, these selected resources are provided for sources of further research and information:

Penetration Testing External links:

Penetration Testing – Amazon Web Services (AWS)

Rhino Security Labs – Deep-Dive Penetration Testing …

Black Hills Information Security – Penetration Testing …

Penetration test External links:

Cyber Smart Defence | Penetration Test Ethical Hacking …

penetration test – Answers – Salesforce Trailblazer …

Standard Penetration Test – Geotechdata.info

Amazon Standard Identification Number External links:

Amazon Standard Identification Number – YouTube

Amazon Standard Identification Number – Infogalactic: …

Arch Linux External links:

ArchLabs Linux – Inspired by BunsenLabs, powered by Arch Linux

Packages | Arch Linux ARM

How To Install Arch Linux Latest Version – OSTechNix

BlackArch Linux External links:

BlackArch Linux – Penetration Testing Distribution

BlackArch Linux · GitHub

BlackArch Linux – Penetration Testing Distribution

Black box External links:

Victoza – Side Effects, Safety Concerns & Black Box Warning

Black Box (TV Series 2014) – IMDb

Chess in a black box: China’s five most powerful people – CNN

Burp Suite External links:

Burp Suite Tutorial – Web Application Penetration Testing

Learn Burp Suite, the Nr. 1 Web Hacking Tool | Udemy

Burp Suite Support Center

CBS Interactive External links:

CBS Interactive – Official Site

Commercial software External links:

Commercial Software Assessment Guideline | …

efile with Commercial Software | Internal Revenue Service

E-file approved commercial software providers for …

Free software External links:

NCH Software – Free Software Downloads and Installs

Free Software and Shareware – Tucows Downloads

Paint.NET – Free Software for Digital Photo Editing

Gentoo Linux External links:

Gentoo Linux – Official Site

Gentoo Linux Enhancement Proposals – Gentoo Linux

IT risk External links:

IT Risk Management and Compliance Solutions | Telos

Magic Quadrant for IT Risk Management Solutions

Massachusetts Institute of Technology External links:

Massachusetts Institute of Technology – ApplyWithUs

Massachusetts Institute of Technology

Massachusetts Institute of Technology – Niche

Metasploit Project External links:

Metasploit Project (@metasploit) | Twitter

Metasploit Project Archives · GitHub

National Security Agency External links:

National Security Agency for Intelligence Careers

NSA – National Security Agency – Home | Facebook

Biography – Executive Director, National Security Agency

OWASP ZAP External links:

File:Owasp zap flyer v2.pdf – OWASP

Parrot Security OS External links:

Parrot Security OS – Computer Company – Facebook

Parrot Security OS 3.7 Released With Linux 4.11, Now …

Payment Card Industry Data Security Standard External links:

[PDF]Payment Card Industry Data Security Standard (PCI …

RAND Corporation External links:

RAND Corporation – GuideStar Profile

RAND Corporation | American think tank | Britannica.com

Risk assessment External links:


Breast Cancer Risk Assessment Tool

Ground Risk Assessment Tool – United States Army …

SANS Institute External links:

SANS Institute

SANS Institute (@SANSInstitute) | Twitter

SANS Institute: ICS Security Training Courses Excerpts

Software system External links:

Software System Update – Nintendo 3DS

Grant Management Software System | eCivis

Standard penetration test External links:

SPT: Standard Penetration Test Energy Calibration

Standard Penetration Test (SPT) Demonstration – YouTube

SPT (Standard Penetration Test) – Geotechnical Drilling

System Development Corporation External links:

Career System Development Corporation – Yelp

System Development Corporation

System Development Corporation

Systems analysis External links:

P E Systems | Systems Analysis | Technology Services

Community: “Virtual Systems Analysis” – TV Club

My Systems Analysis Ch. 12 Flashcards | Quizlet

Tiger team External links:

Urban Dictionary: tiger team
www.urbandictionary.com/define.php?term=tiger team

Garrison Stuttgart’s Windows 10 Tiger Team roars into …

Tiger team
A tiger team is a group of experts assigned to investigate and/or solve technical or systemic problems. A 1964 paper defined the term as “a team of undomesticated and uninhibited technical specialists, selected for their experience, energy, and imagination, and assigned to track down relentlessly every possible source of failure in a spacecraft subsystem.”

Tiger teams External links:

[PDF]Tiger Teams Provide Coalitions Technical and Market …

Rawlings Tigers Baseball | Tiger Teams

United States Department of Defense External links:

United States Department of Defense

United States Department of Defense Standards of …

White box External links:

Avery Permanent Shipping Labels With TrueBlock Technology 2 x 4 White Box Of 1000 at Office Depot & OfficeMax. Now One Company.

BackerKit Pledge Manager for The White Box: A Game …