Pre-Engagement

Pre-Enagement

Pre-Engagement is the stage of preparation for the actual pentest. During this stage, questions are asked contracts are made. The client informs the team what they want tested and how.

Components

1. Non-Disclosure Agreement

2. Scoping Questionnaire

3. Pre-Engagement Meeting

4. Kick-Off Meeting

Non-Disclosure Agreement (NDA)

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.

Documents

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

Scoping Questionnaire

Helps to better understand what the client wants performed. The scoping questionnaire should clearly explain the services offered and what they require.

Potential Services:

• Internal Vulnerability Assessment

• Internal Penetration Test

• External Vulnerability Assessment

• External Penetration Test

• Wireless Security Assessment

• Physical Security Assessment

• Application Security Assessment

• Social Engineering Assessment

• Web Application Security Assessment

• Red Team Assessment

At this stage, other vital information should be collected such as:

• How many expected live hosts?

• How many IPs/CIDR ranges in scope?

• How many domains/subdomains in scope?

• How many wireless SSIDs in scope?

• How many web/mobile applications?

Pre-Engagement Meeting

This meeting discusses all relevant and essential components with the customer before the penetration test. This information as well as the info collected from the Scoping Questionnaire will serve as input for the Penetration Testing Proposal. The scoping questionnaire may be discussed in this meeting to give more details or explain one of the services

Contract

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 the end date for the penetration test. This gives us a precise time window to perform the test and helps us plan our procedure. It is also vital to explicitly ask how time windows the individual attacks (Exploitation / Post-Exploitation / Lateral Movement) are to be carried out. 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	Finally, prices and the terms of payment are explained.

Rules of Engagement (RoE)

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

Kick-Off Meeting

The pentesting team will go over the nature of the penetration test and how it will take place. The team also goes over vulnerability disclosure and potential risks of a penetration test.