April 21, 2021

Penetration testing 101

What is a penetration test?

A penetration test is an authorized assessment conducted by highly specialized third-party security experts to discover and report on vulnerabilities and attack paths in your networks, systems, and applications. Penetration testers use hacker tools but for good cause. 

A company will need to remediate the high-risk findings as soon as reported by penetration testers to reduce the attack surface before the hackers exploit them.

Penetration testing is required to meet auditors' requirements by most security certifications like ISO 27001 or attestations like SOC2 and to comply with cybersecurity and privacy-related laws of the land like HIPAA or industry-specific regulations like PCI.

Why do you need a penetration test?

Your company's internet-facing assets are getting hit with thousands of malicious connection requests as you read this blog post. Don't believe me? Ask your WAF provider to show you a recent report of blocked IPs trying to scan your website. 

Though you may assume “it cannot happen to me” or that your business is too small to be an attractive target to bad actors, this type of thinking can pose big risks. Hackers take the path of least resistance - choosing to go after unlikely targets like suppliers and service companies than after large enterprises with an army of security forces, and they are motivated by a variety of reasons - from profit, activism, espionage, revenge, identity theft, IP theft, or just plain disruption and denial of service.

Below are a few reasons why you may want to consider a penetration test - 

Protect Your Valuable Product & Customers : You're in business to earn customers' trust and serve them. You have raised millions to build something great. You're responsible for protecting your product and your customer data and identities even if you have your application deployed in the cloud based on a shared responsibility model. Customers may ask for you to provide evidence of an annual third-party penetration test as part of their procurement, legal, and security due diligence. 

Protect Your Data: If you're storing any PII/ PHI/PCI data in your environment and if you fail to protect the security and privacy of your customers' data, you're subject to steep monetary penalties by legal and regulatory oversight authorities in your industry. According to the Dark Web Market Price Index published in 2021, everything from credit cards, PayPal accounts, crypto accounts, social media accounts, streaming accounts, forged IDs and documents, email dumps fetch prices ranging from $50 to $4,000 per item. Regular penetration tests can discover misconfigurations, weak encryptions, known vulnerabilities, default credentials, and sensitive data inadvertently exposed by your APIs, applications and data stores.

Continuous Security Validation: Penetration testing can verify if your security tools such as WAF or Email Filters are working as advertised. It can also identify any changes, for better or worse, to your company’s security posture as your business activities, users, employees, partners, and competitors continuously change.

Meet Compliance Requirements: A penetration test report or letter of attestation from a penetration tester is often required by your regulators, insurance companies, and clients' vendor management to assure that you have a good threat and vulnerability management practice in place.

Achieve and maintain security certifications and attestations: A penetration test is required by SOC 2 and ISO 27001 auditors to confirm the evidence of a mature threat and vulnerability management practice.

SOC 2:

SOC 2 compliance requirements directly mention the use of penetration testing or similar techniques to identify vulnerabilities in the company’s systems – which is why most auditors require a penetration test as part of the SOC 2 process.

CC4.1 – Management uses a variety of different types of ongoing and separate evaluations, including penetration testing, independent certifications made against established specifications (for example, ISO certifications), and internal audit assessments.

CC7.1 – The entity uses detection and monitoring procedures to identify (1) changes to configurations that result in the introduction of new vulnerabilities, and (2) susceptibilities to newly discovered vulnerabilities.

ISO 27001:

ISO 27001 requires that a company prevent the exploitation of technical vulnerabilities. Performing vulnerability scanning and assessment on your network and applications may identify vulnerabilities with false positives or generic CVSS scores. Therefore, it’s important to combine vulnerability tools' scanning results with a third-party manual penetration test to provide accurate evidence to your auditor on the following requirement.

A.12.6.1 – Information about technical vulnerabilities of information systems being used shall be obtained in a timely fashion, the organization’s exposure to such vulnerabilities evaluated and appropriate measures taken to address the associated risk.

Types of penetration tests

There are 2 ways to think about penetration tests: 

  1. Testing for external hacking attacks
  2. Testing for insider threats

Blackbox: The penetration tester will not ask for any test accounts or authentication to your applications and infrastructure components ( databases or servers). The penetration tester will attack the externally facing systems without much knowledge of the systems using public breach databases or using social logins (if present)and try to exploit any externally facing vulnerabilities, misconfigurations, and defaults. These are quick and low-cost tests.

Whitebox:  You will provision test accounts and allow the penetration tester to conduct authenticated manual testing of vulnerabilities. These tests would cover internally facing risks and provide maximum assurance. They are also time-consuming and expensive.

Attack Vectors:

You may choose the attack vectors you'd like the penetration testers to test for vulnerabilities.

  • Network: You provide a range of IP addresses and active hosts within that range.
  • Applications: You provide production URLs and any subdomains to test for web apps or binaries /devices /links for mobile applications or demo/test versions of the applications that mimic production apps and environment.
  • APIs: You provide # of API endpoints and # of calls
  • Physical: On-site attacks to access physical network devices, and wireless access points.
  • People: You may or may not provide a list of target emails. Penetration testers can research social media and various open-source intelligence sources to identify target lists, buy domains that look like yours, and set up servers in the cloud to bypass your email filters and deliver phishing links to your target users and take control of their machines.
  • Cloud: Penetration testers will try to exploit cloud-based services, serverless functions, containers, SQL/no-sql stores, APIs, and consoles to attack your applications.
  • IOT devices: any hardware device with an IP address is a target. If these devices are set up with default credentials, they can be an easy target of an attack.

Process and time commitment

Most penetration testing companies generally follow the process below:


  1. Scoping call to get a quote
  2. Sign SOW and NDA/MSA
  3. Kick-off Test

During Test

  1. Information Gathering
  2. Vulnerability Scanning
  3. Exploitation
  4. Post-Exploitation
  5. Preliminary Reporting


  1. Report review call
  2. Remediation/ Retest
  3. Final Report

The time commitment for this process depends on the type of penetration test you are pursuing.

If it's a black box test with no authentication, the tester may be able to finish most of the work without much involvement from your team during the testing period.

A whitebox test may take some involvement during the test. If you have a large and complex network and access provisioning process, or if you have a complex procurement and legal contract review process, it may take more time on your part to engage a third-party penetration  tester.

For most penetration testing companies, it takes one to four weeks to complete a penetration test depending on the size and scope of the attack vectors.

While the test itself may not take much of your time, you should allocate enough time to fix vulnerabilities that the penetration test uncovers. Typical remediation cycles can take 90-180 days depending on the availability of your resources. 

It’s important that you budget enough time for these considerations - as well as some additional lead time as penetration test companies may not be able to start your test right away.  

How often do you need a penetration test?

Most Auditors if not client vendor risk managers will require that you conduct a third party penetration test twice if not at least once a year. You should choose your penetration test partner who can accommodate penetration tests at regular intervals for an affordable price. The penetration test must be completed before the end of your SOC 2 observation period in order to be included in your control matrix.

How much does a penetration test cost?

The cost of a penetration test can vary depending on the size of your apps, the number of attack vectors, and the type of test you choose. You will have to go through a scoping exercise to get an accurate quote. It can also depend on the penetration testing company's rate card. Large penetration testing companies and higher rates do not necessarily mean that you are getting top-quality results and attention. Typically these tests start at $5,000 and can go up to $15,000 depending on the scope and who you are talking to. 

Your penetration testing partner should match your expectations and below is a guideline you can follow to find your match.

How to choose a penetration testing company:

Anyone with an internet connection and some hacking tools can hit your systems but here are some things to consider when evaluating a “security partner”:

  1. Look for a CREST accredited partner: CREST is the only international certification authority that audits and approves penetration testing organizations for their methodologies, processes, and client data handling practices.

  1. Look for testers' certifications: You may ask for the profile of the tester touching your systems and data. You should be looking for hands-on lab-based certs like OSCP, CRTP, OSCE, GXPN, GPEN, GWAPT, GAWN, GCIH, GCFA, GMOB, GCIA, GSEC, etc.

  1. Get a clear Statement of Work: The SOW should clearly state what's included, and what's not included in the test. It should have clear timelines for deliverables. Ideally, you should choose a penetration testing company with an all-inclusive fixed price. For those who wish to pay on a time and expense basis, know that pre-test research, set up, and post-test remediation tests paid on an hourly basis can quickly add up. The SOW should include an escalation and remediation process and contacts in case the testing impacts your services.

  1. Risk Analysis: The penetration testing company shouldn't just hand you a list of vulnerabilities without any business impact analysis to reflect the reality of the risks facing your organization. They should be flexible to accommodate your risk appetite and decision to accept or not accept risks.

  1. Insurance Requirements: Make sure they have adequate insurance to cover any professional liability due to penetration testing activities.

  1. Report Quality: Experienced auditors and vendor risk managers can challenge the validity of a penetration test done by inexperienced testers. If the testers do not follow industry best practices and methodologies, your report will not support legal liability and forensic cases.

Penetration testing will help secure new clients, protect your business assets, prevent financial frauds, and help you avoid fines for non-compliance. Penetration testing fulfills multiple purposes in a company’s risk management strategy.

About Prescient Security

Prescient Security is a global top 20 penetration testing company based in New York City, offering expert Security Reviews and Security Testing Services to financial, healthcare, and Hitech clients. Prescient Security is a CREST certified security testing organization and adheres to the highest safety and security standards for handling client data. We offer Vulnerability Scanning, Continuous and Automated Penetration Testing as a Service, Agile Web App Security Testing, Red/Blue/Purple Teaming, Cloud Security Assessment, Soc2/HIPAA/CSA Star Audit, BCP/DR/IR Testing, Virtual/Fractional CISO, and Security Staffing. Our mission is to achieve quantifiable risk remediation and return for every dollar you invest in security. For more information on our partnership with Vanta, please visit

About Vanta

‍Vanta is your automated security and compliance expert. Our continuous monitoring software and robust range of automated checks can help your company get SOC 2, HIPAA, or ISO 27001 compliance-ready fast — and also bolster your holistic security posture.


Determine whether the GDPR applies to you and if so, if you are a processor or controller (or both)

Do you sell goods or service in the EU or UK?

Do you sell goods or services to EU businesses, consumers, or both?

Do you have employees in the EU or UK?

Do persons from the EU or UK visit your website?

Do you monitor the behavior of persons within the EU?

If any of the above apply to your business, you’ll need to get GDPR compliant.

Create a Data Map by taking the following actions

Identify and document every system (i.e. database, application, or vendor) which stores or processes EU or UK based personally identifiable information (PII)

Document the retention periods for PII in each system

Determine whether you collect, store, or process “special categories” of data

racial or ethnic origins
genetic data
political opinions
biometric data that can uniquely identifying someone
religious or philosophical beliefs
health, sex life or sexual orientation data
trade union membership

Determine whether your Data Map meets the requirements for Records of Processing Activities (Art. 30)

the name and contact details of the controller
the purpose behind the processing of data
a description of the categories of data that will be processed
who will receive the data including data
documentation of suitable safeguards for data transfers to a third country or an international organization
the retention period of the different categories of data
a general description of the technical and organizational security measures

Determine whether your Data Map includes the following information about processing activities carried out by vendors on your behalf

the name and contact details of the processor or processors and of each controller on behalf of which the processor is acting, and, where applicable, of the controller’s or the processor’s representative, and the data protection officer
the categories of processing carried out on behalf of each controller
documentation of suitable safeguards for data transfers to a third country or an international organization
a general description of the technical and organizational security measures

Determine your grounds for processing data

For each category of data and system/application have you determined the lawful basis for processing based on one of the following conditions?

consent of the data subject
contract with the data subject
necessary for compliance with a legal obligation
necessary in order to protect the vital interests of the data subject or a third party
necessary for the performance of a task in the public interest or in the exercise of official authority vested in the controller
necessary for the purposes of the legitimate interests pursued by the controller or by a third party, except where such interests are overridden by the rights of data subject

Take inventory of current customer and vendor contracts to confirm new GDPR-required flow-down provisions are included

Review all customer contracts to determine that they have appropriate contract language (i.e. Data Protection Addendums with Standard Contractual Clauses)

Review all in-scope vendor contracts to determine that they have appropriate contract language (i.e. Data Protection Addendums with Standard Contractual Clauses)

Do your agreements cover the following items?
vendor shall process the personal data only on documented instructions (including when making an international transfer of personal data) unless it is required to do otherwise by EU or member state law
vendor ensures that persons authorized to process the personal data are subject to confidentiality undertakings or professional or statutory obligations of confidentiality.
vendor have adequate information security in place, technical and organizational measures to be met to support data subject requests or breaches
vendor shall not appoint or disclose any personal data to any sub-processor unless required or authorized
vendor shall delete or return all the personal data after the end of the provision of services relating to processing, and deletes existing copies unless Union or Member State law requires storage of the personal data;
vendor makes available all information necessary to demonstrate compliance and allow for and contribute to audits, including inspections

Have you performed a risk assessment on vendors who are processing your PII?


Determine if you need to do a Data Protection Impact Assessment

Is your data processing taking into account the nature, scope, context, and purposes of the processing, likely to result in a high risk to the rights and freedoms of natural persons?

Does your processing involve any of the following?
automated processing, including profiling, and on which decisions are based that produce legal effects
special categories of data or data related to criminal convictions and offenses
monitor publicly accessible area on a large scale.
If any of the above are true, you may need to conduct a Data Protection Impact Assessment for existing and new data projects.

Review product and service design (including your website or app) to ensure privacy notice links, marketing consents, and other requirements are integrated

Do you have a public-facing Privacy Policy which covers the use of all your products,  services and websites?

Does the notice to the data subject include the following items?

the identity and the contact details of the organization and its representative
the contact details of the data protection officer, if applicable
the purposes to process personal data and its legal basis for the processing
the recipients or categories of recipients of the personal data, if any
the details regarding any transfer of personal data to a third country and the safeguards taken applicable

Does the notice also include the following items?

the retention period, or if that is not possible, the criteria used to determine that period
the existence of the data subject rights (i.e. requests for information, modification or deletion of PII)
the right to withdraw consent at any time
the right to lodge a complaint with a supervisory authority
whether the provision of personal data is a statutory or contractual requirement, or a requirement necessary to enter into a contract, as well as whether the data subject is obliged to provide the personal data and of the possible consequences of failure to provide such data
the existence of automated decision-making, including profiling, and meaningful information about the logic involved, as well as the significance and the consequences

Do you have a mechanism for persons to change or withdraw consent?


Update internal privacy policies to comply with notification obligations

Update internal privacy notices for EU employees

Do you have an Employee Privacy Policy governing the collection and use of EU and UK employee data?

Determine if you need to appoint a Data Protection Officer, and appoint one if needed

Have you determined whether or not you must designate a Data Protection Officer (DPO) based on one of the following conditions (Art. 37)?

the data processing is carried out by a public authority
the core activities of the controller or processor require regular and systematic monitoring of data subjects on a large scale

If you export data from the EU, consider if you need a compliance mechanism to cover the data transfer, such as model clauses

If you transfer, store, or process data outside the EU or UK, have you identified your legal basis for the data transfer (note: most likely covered by the Standard Contractual Clauses)

Have you performed and documented a Transfer Impact Assessment (TIA)?


Confirm you are complying with other data subject rights (i.e. aside from notification)

Do you have a defined process for timely response to Data Subject Access Requests (DSAR) (i.e. requests for information, modification or deletion of PII)?

Are you able to provide the subject information in a concise, transparent, intelligible and easily accessible form, using clear and plain language?

Do you have a process for correcting or deleting data when requested?

Do you have an internal policy regarding a Compelled Disclosure from Law Enforcement?


Determine if you need to appoint an EU-based representative, and appoint one if needed

Have you appointed an EU Representative or determined that an EU Representative is not needed based on one of the following conditions?

data processing is occasional
data processing is not on a large scale
data processing doesn’t include special categories or data related to criminal convictions and offenses
doesn’t risk to the rights and freedoms of data subjects
a public authority or body

If operating in more than one EU state, identify a lead Data Protection Authority (DPA)

Do you operate in more than one EU state?

If so, have you designated the Supervisory Authority of the main establishment to act as your Lead Supervisory Authority?


Implement Employee Trainings to Demonstrate Compliance with GDPR Principles and Data Subject Rights

Have you provided appropriate Security Awareness and Privacy training to your staff?


Update internal procedures and policies to ensure you can comply with data breach response requirements

Have you created and implemented an Incident Response Plan which included procedures for reporting a breach to EU and UK Data Subjects as well as appropriate Data Authorities?

Do breach reporting policies comply with all prescribed timelines and include all recipients i.e. authorities, controllers, and data subjects?


Implement appropriate technical and organizational measures to ensure a level of security appropriate to the risk

This includes pseudonymization/ encryption, maintaining confidentiality, restoration of access following physical/technical incidents and regular testing of measures

Have you implemented encryption of PII at rest and in transit?

Have you implemented pseudonymization?

Have you implemented appropriate physical security controls?

Have you implemented information security policies and procedures?

Can you access EU or UK PII data in the clear?

Do your technical and organizational measure ensure that, by default, only personal data which are necessary for each specific purpose of the processing are processed?


Consider streamlining GDPR compliance with automation

Transform manual data collection and observation processes into continuous monitoring

Download this checklist for easy reference

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Develop a roadmap for successful implementation of an ISMS and ISO 27001 certification

Implement Plan, Do, Check, Act (PDCA) process to recognize challenges and identify gaps for remediation

Consider ISO 27001 certification costs relative to org size and number of employees

Clearly define scope of work to plan certification time to completion

Select an ISO 27001 auditor


Set the scope of your organization’s ISMS

Decide which business areas are covered by the ISMS and which are out of scope

Consider additional security controls for business processes that are required to pass ISMS-protected information across the trust boundary

Inform stakeholders regarding scope of the ISMS


Establish an ISMS governing body

Build a governance team with management oversight

Incorporate key members of top management, e.g. senior leadership and executive management with responsibility for strategy and resource allocation


Conduct an inventory of information assets

Consider all assets where information is stored, processed, and accessible

  • Record information assets: data and people
  • Record physical assets: laptops, servers, and physical building locations
  • Record intangible assets: intellectual property, brand, and reputation

Assign to each asset a classification and owner responsible for ensuring the asset is appropriately inventoried, classified, protected, and handled


Execute a risk assessment

Establish and document a risk-management framework to ensure consistency

Identify scenarios in which information, systems, or services could be compromised

Determine likelihood or frequency with which these scenarios could occur

Evaluate potential impact of each scenario on confidentiality, integrity, or availability of information, systems, and services

Rank risk scenarios based on overall risk to the organization’s objectives


Develop a risk register

Record and manage your organization’s risks

Summarize each identified risk

Indicate the impact and likelihood of each risk


Document a risk treatment plan

Design a response for each risk (Risk Treatment)

Assign an accountable owner to each identified risk

Assign risk mitigation activity owners

Establish target dates for completion of risk treatment activities


Complete the Statement of Applicability worksheet

Review 114 controls of Annex A of ISO 27001 standard

Select controls to address identified risks

Complete the Statement of Applicability listing all Annex A controls, justifying inclusion or exclusion of each control in the ISMS implementation


Continuously assess and manage risk

Build a framework for establishing, implementing, maintaining, and continually improving the ISMS

Include information or references to supporting documentation regarding:

  • Information Security Objectives
  • Leadership and Commitment
  • Roles, Responsibilities, and Authorities
  • Approach to Assessing and Treating Risk
  • Control of Documented Information
  • Communication
  • Internal Audit
  • Management Review
  • Corrective Action and Continual Improvement
  • Policy Violations

Assemble required documents and records

Review ISO 27001 Required Documents and Records list

Customize policy templates with organization-specific policies, process, and language


Establish employee training and awareness programs

Conduct regular trainings to ensure awareness of new policies and procedures

Define expectations for personnel regarding their role in ISMS maintenance

Train personnel on common threats facing your organization and how to respond

Establish disciplinary or sanctions policies or processes for personnel found out of compliance with information security requirements


Perform an internal audit

Allocate internal resources with necessary competencies who are independent of ISMS development and maintenance, or engage an independent third party 

Verify conformance with requirements from Annex A deemed applicable in your ISMS's Statement of Applicability

Share internal audit results, including nonconformities, with the ISMS governing body and senior management

Address identified issues before proceeding with the external audit


Undergo external audit of ISMS to obtain ISO 27001 certification

Engage an independent ISO 27001 auditor

Conduct Stage 1 Audit consisting of an extensive documentation review; obtain feedback regarding readiness to move to Stage 2 Audit

Conduct Stage 2 Audit consisting of tests performed on the ISMS to ensure proper design, implementation, and ongoing functionality; evaluate fairness, suitability, and effective implementation and operation of controls


Address any nonconformities

Ensure that all requirements of the ISO 27001 standard are being addressed

Ensure org is following processes that it has specified and documented

Ensure org is upholding contractual requirements with third parties

Address specific nonconformities identified by the ISO 27001 auditor

Receive auditor’s formal validation following resolution of nonconformities


Conduct regular management reviews

Plan reviews at least once per year; consider a quarterly review cycle 

Ensure the ISMS and its objectives continue to remain appropriate and effective

Ensure that senior management remains informed

Ensure adjustments to address risks or deficiencies can be promptly implemented


Calendar ISO 27001 audit schedule and surveillance audit schedules

Perform a full ISO 27001 audit once every three years

Prepare to perform surveillance audits in the second and third years of the Certification Cycle


Consider streamlining ISO 27001 certification with automation

Transform manual data collection and observation processes into automated and continuous system monitoring

Identify and close any gaps in ISMS implementation in a timely manner


Learn more about achieving ISO 27001 certification with Vanta

Book an ISO 27001 demo with Vanta

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Determine which annual audits and assessments are required for your company

Perform a readiness assessment and evaluate your security against HIPAA requirements

Review the U.S. Dept of Health and Human Services Office for Civil Rights Audit Protocol


Conduct required HIPAA compliance audits and assessments

Perform and document ongoing technical and non-technical evaluations, internally or in partnership with a third-party security and compliance team like Vanta


Document your plans and put them into action

Document every step of building, implementing, and assessing your compliance program

Vanta’s automated compliance reporting can streamline planning and documentation


Appoint a security and compliance point person in your company

Designate an employee as your HIPAA Compliance Officer


Schedule annual HIPAA training for all employees

Distribute HIPAA policies and procedures and ensure staff read and attest to their review


Document employee trainings and other compliance activities

Thoroughly document employee training processes, activities, and attestations


Establish and communicate clear breach report processes
to all employees

Ensure that staff understand what constitutes a HIPAA breach, and how to report a breach

Implement systems to track security incidents, and to document and report all breaches


Institute an annual review process

Annually assess compliance activities against theHIPAA Rules and updates to HIPAA


Continuously assess and manage risk

Build a year-round risk management program and integrate continuous monitoring

Understand the ins and outs of HIPAA compliance— and the costs of noncompliance

Download this checklist for easy reference

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