Pre-Engagement
Pre-engagement is the stage of preparation for the actual penetration test. During this stage, many questions are asked, and some contractual agreements are made. The client informs us about what they
The entire pre-engagement process consists of three essential components:
Scoping questionnaire
Pre-engagement meeting
Kick-off meeting
Before any of these can be discussed in detail, a Non-Disclosure Agreement (NDA) must be signed by all parties. There are several types of NDAs:
Type
Description
Unilateral NDA
This type of NDA obligates only one party to maintain confidentiality and allows the other party to share the information received with third parties.
Bilateral NDA
In this type, both parties are obligated to keep the resulting and acquired information confidential. This is the most common type of NDA that protects the work of penetration testers.
Multilateral NDA
Multilateral NDA is a commitment to confidentiality by more than two parties. If we conduct a penetration test for a cooperative network, all parties responsible and involved must sign this document.
t is essential to know who in the company is permitted to contract us for a penetration test. Because we cannot accept such an order from everyone.
Chief Executive Officer (CEO)
Chief Technical Officer (CTO)
Chief Information Security Officer (CISO)
Chief Security Officer (CSO)
Chief Risk Officer (CRO)
Chief Information Officer (CIO)
VP of Internal Audit
Audit Manager
VP or Director of IT/Information Security
It is vital to determine early on in the process who has signatory authority for the contract, Rules of Engagement documents, and who will be the primary and secondary points of contact, technical support, and contact for escalating any issues.
This stage also requires the preparation of several documents before a penetration test can be conducted that must be signed by our client and us so that the declaration of consent can also be presented in written form if required. Otherwise the penetration test could breach the Computer Misuse Act. These documents include, but are not limited to:
Document
Timing for Creation
1. Non-Disclosure Agreement (NDA)
After Initial Contact
2. Scoping Questionnaire
Before the Pre-Engagement Meeting
3. Scoping Document
During the Pre-Engagement Meeting
4. Penetration Testing Proposal (Contract/Scope of Work (SoW))
During the Pre-engagement Meeting
5. Rules of Engagement (RoE)
Before the Kick-Off Meeting
6. Contractors Agreement (Physical Assessments)
Before the Kick-Off Meeting
7. Reports
During and after the conducted Penetration Test
Note: Our client may provide a separate scoping document listing in-scope IP addresses/ranges/URLs and any necessary credentials but this information should also be documented as an appendix in the RoE document.
Important Note:
These documents should be reviewed and adapted by a lawyer after they have been prepared.
Scoping Questionnaire
After initial contact is made with the client, we send them a Scoping Questionnaire to better understand the services they are seeking. This scoping questionnaire should clearly explain our services and may typically ask them to choose one or more from the following list:
☐ Internal Vulnerability Assessment
☐ External Vulnerability Assessment
☐ Internal Penetration Test
☐ External Penetration Test
☐ Wireless Security Assessment
☐ Application Security Assessment
☐ Physical Security Assessment
☐ Social Engineering Assessment
☐ Red Team Assessment
☐ Web Application Security Assessment
How many expected live hosts?
How many IPs/CIDR ranges in scope?
How many Domains/Subdomains are in scope?
How many wireless SSIDs in scope?
How many web/mobile applications? If testing is authenticated, how many roles (standard user, admin, etc.)?
For a phishing assessment, how many users will be targeted? Will the client provide a list, or we will be required to gather this list via OSINT?
If the client is requesting a Physical Assessment, how many locations? If multiple sites are in-scope, are they geographically dispersed?
What is the objective of the Red Team Assessment? Are any activities (such as phishing or physical security attacks) out of scope?
Is a separate Active Directory Security Assessment desired?
Will network testing be conducted from an anonymous user on the network or a standard domain user?
Do we need to bypass Network Access Control (NAC)?
Finally, we will want to ask about information disclosure and evasiveness (if applicable to the assessment type):
Is the Penetration Test black box (no information provided), grey box (only IP address/CIDR ranges/URLs provided), white box (detailed information provided)
Would they like us to test from a non-evasive, hybrid-evasive (start quiet and gradually become "louder" to assess at what level the client's security personnel detect our activities), or fully evasive.
Contract - Checklist
Checkpoint
Description
☐ NDA
Non-Disclosure Agreement (NDA) refers to a secrecy contract between the client and the contractor regarding all written or verbal information concerning an order/project. The contractor agrees to treat all confidential information brought to its attention as strictly confidential, even after the order/project is completed. Furthermore, any exceptions to confidentiality, the transferability of rights and obligations, and contractual penalties shall be stipulated in the agreement. The NDA should be signed before the kick-off meeting or at the latest during the meeting before any information is discussed in detail.
☐ Goals
Goals are milestones that must be achieved during the order/project. In this process, goal setting is started with the significant goals and continued with fine-grained and small ones.
☐ Scope
The individual components to be tested are discussed and defined. These may include domains, IP ranges, individual hosts, specific accounts, security systems, etc. Our customers may expect us to find out one or the other point by ourselves. However, the legal basis for testing the individual components has the highest priority here.
☐ Penetration Testing Type
When choosing the type of penetration test, we present the individual options and explain the advantages and disadvantages. Since we already know the goals and scope of our customers, we can and should also make a recommendation on what we advise and justify our recommendation accordingly. Which type is used in the end is the client's decision.
☐ Methodologies
Examples: OSSTMM, OWASP, automated and manual unauthenticated analysis of the internal and external network components, vulnerability assessments of network components and web applications, vulnerability threat vectorization, verification and exploitation, and exploit development to facilitate evasion techniques.
☐ Penetration Testing Locations
External: Remote (via secure VPN) and/or Internal: Internal or Remote (via secure VPN)
☐ Time Estimation
For the time estimation, we need the start and end dates for the penetration test. This provides a precise time window to perform the test and helps us plan our procedure. It is also vital to explicitly determine the duration of the time windows for each phase of the attack, such as Exploitation, Post-Exploitation, and Lateral Movement. These can be carried out during or outside regular working hours. When testing outside regular working hours, the focus is more on the security solutions and systems that should withstand our attacks.
☐ Third Parties
For the third parties, it must be determined via which third-party providers our customer obtains services. These can be cloud providers, ISPs, and other hosting providers. Our client must obtain written consent from these providers describing that they agree and are aware that certain parts of their service will be subject to a simulated hacking attack. It is also highly advisable to require the contractor to forward the third-party permission sent to us so that we have actual confirmation that this permission has indeed been obtained.
☐ Evasive Testing
Evasive testing is the test of evading and passing security traffic and security systems in the customer's infrastructure. We look for techniques that allow us to find out information about the internal components and attack them. It depends on whether our contractor wants us to use such techniques or not.
☐ Risks
We must also inform our client about the risks involved in the tests and the possible consequences. Based on the risks and their potential severity, we can then set the limitations together and take certain precautions.
☐ Scope Limitations & Restrictions
It is also essential to determine which servers, workstations, or other network components are essential for the client's proper functioning and its customers. We will have to avoid these and must not influence them any further, as this could lead to critical technical errors that could also affect our client's customers in production.
☐ Information Handling
HIPAA, PCI, HITRUST, FISMA/NIST, etc.
☐ Contact Information
For the contact information, we need to create a list of each person's name, title, job title, e-mail address, phone number, office phone number, and an escalation priority order.
☐ Lines of Communication
It should also be documented which communication channels are used to exchange information between the customer and us. This may involve e-mail correspondence, telephone calls, or personal meetings.
☐ Reporting
Apart from the report's structure, any customer-specific requirements the report should contain are also discussed. In addition, we clarify how the reporting is to take place and whether a presentation of the results is desired.
☐ Payment Terms
Rules of Engagement - Checklist
Checkpoint
Contents
☐ Introduction
Description of this document.
☐ Contractor
Company name, contractor full name, job title.
☐ Penetration Testers
Company name, pentesters full name.
☐ Contact Information
Mailing addresses, e-mail addresses, and phone numbers of all client parties and penetration testers.
☐ Purpose
Description of the purpose for the conducted penetration test.
☐ Goals
Description of the goals that should be achieved with the penetration test.
☐ Scope
All IPs, domain names, URLs, or CIDR ranges.
☐ Lines of Communication
Online conferences or phone calls or face-to-face meetings, or via e-mail.
☐ Time Estimation
Start and end dates.
☐ Time of the Day to Test
Times of the day to test.
☐ Penetration Testing Type
External/Internal Penetration Test/Vulnerability Assessments/Social Engineering.
☐ Penetration Testing Locations
Description of how the connection to the client network is established.
☐ Methodologies
OSSTMM, PTES, OWASP, and others.
☐ Objectives / Flags
Users, specific files, specific information, and others.
☐ Evidence Handling
Encryption, secure protocols
☐ System Backups
Configuration files, databases, and others.
☐ Information Handling
Strong data encryption
☐ Incident Handling and Reporting
Cases for contact, pentest interruptions, type of reports
☐ Status Meetings
Frequency of meetings, dates, times, included parties
☐ Reporting
Type, target readers, focus
☐ Retesting
Start and end dates
☐ Disclaimers and Limitation of Liability
System damage, data loss
☐ Permission to Test
Signed contract, contractors agreement
Contractors Agreement
If the penetration test also includes physical testing, then an additional contractor's agreement is required. Since it is not only a virtual environment but also a physical intrusion, completely different laws apply here. It is also possible that many of the employees have not been informed about the test. Suppose we encounter employees with a very high-security awareness during the physical attack and social engineering attempts, and we get caught. In that case, the employees will, in most cases, contact the police. This additional contractor's agreement is our "get out of jail free card" in this case.
Contractors Agreement - Checklist for Physical Assessments
Checkpoint
☐ Introduction
☐ Contractor
☐ Purpose
☐ Goal
☐ Penetration Testers
☐ Contact Information
☐ Physical Addresses
☐ Building Name
☐ Floors
☐ Physical Room Identifications
☐ Physical Components
☐ Timeline
☐ Notarization
☐ Permission to Test
Last updated