Preparation

Precautionary Measures during Penetration Tests

• Obtain written consent from the owner or authorized representative of the computer or network being tested

• Conduct the testing within the scope of the consent obtained only and respect any limitations specified

• Take measures to prevent causing damage to the systems or networks being tested

• Do not access, use or disclose personal data or any other information obtained during the testing without permission

• Do not intercept electronic communications without the consent of one of the parties to the communication

• Do not conduct testing on systems or networks that are covered by the Health Insurance Portability and Accountability Act (HIPAA) without proper authorization

Pentesting Stages

Pre-Engagement

Pre-engagement is educating the client and adjusting the contract. All necessary tests and their components are strictly defined and contractually recorded. In a face-to-face meeting or conference call, many arrangements are made, such as:

• Non-Disclosure Agreement

• Goals

• Scope

• Time Estimation

• Rules of Engagement

Information Gathering

Information gathering describes how we obtain information about the necessary components in various ways. We search for information about the target company and the software and hardware in use to find potential security gaps that we may be able to leverage for a foothold.

Vulnerability Assessment

Once we get to the Vulnerability Assessment stage, we analyze the results from our Information Gathering stage, looking for known vulnerabilities in the systems, applications, and various versions of each to discover possible attack vectors. Vulnerability assessment is the evaluation of potential vulnerabilities, both manually and through automated means. This is used to determine the threat level and the susceptibility of a company's network infrastructure to cyber-attacks.

Exploitation

In the Exploitation stage, we use the results to test our attacks against the potential vectors and execute them against the target systems to gain initial access to those systems.

Post-Exploitation

At this stage of the penetration test, we already have access to the exploited machine and ensure that we still have access to it even if modifications and changes are made. During this phase, we may try to escalate our privileges to obtain the highest possible rights and hunt for sensitive data such as credentials or other data that the client is concerned with protecting (pillaging). Sometimes we perform post-exploitation to demonstrate to a client the impact of our access. Other times we perform post-exploitation as an input to the lateral movement process described next.

Lateral Movement

Lateral movement describes movement within the internal network of our target company to access additional hosts at the same or a higher privilege level. It is often an iterative process combined with post-exploitation activities until we reach our goal. For example, we gain a foothold on a web server, escalate privileges and find a password in the registry. We perform further enumeration and see that this password works to access a database server as a local admin user. From here, we can pillage sensitive data from the database and find other credentials to further our access deeper into the network. In this stage, we will typically use many techniques based on the information found on the exploited host or server.

Proof-of-Concept

In this stage, we document, step-by-step, the steps we took to achieve network compromise or some level of access. Our goal is to paint a picture of how we were able to chain together multiple weaknesses to reach our goal so they can see a clear picture of how each vulnerability fits in and help prioritize their remediation efforts. If we don't document our steps well, it's hard for the client to understand what we were able to do and, thus, makes their remediation efforts more difficult. If feasible, we could create one or more scripts to automate the steps we took to assist our client in reproducing our findings. We cover this in-depth in the Documentation & Reporting module.

Post-Engagement

During post-engagement, detailed documentation is prepared for both administrators and client company management to understand the severity of the vulnerabilities found. At this stage, we also clean up all traces of our actions on all hosts and servers. During this stage, we create the deliverables for our client, hold a report walkthrough meeting, and sometimes deliver an executive presentation to target company executives or their board of directors. Lastly, we will archive our testing data per our contractual obligations and company policy. We will typically retain this data for a set period or until we perform a post-remediation assessment (retest) to test the client's fixes.

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Pre-engagement

The entire pre-engagement process consists of three essential components:

1. Scoping questionnaire

2. Pre-engagement meeting

3. Kick-off meeting

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

☐ 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

Under each of these, the questionnaire should allow the client to be more specific about the required assessment. Do they need a web application or mobile application assessment? Secure code review? Should the Internal Penetration Test be black box and semi-evasive? Do they want just a phishing assessment as part of the Social Engineering Assessment or also vishing calls?

Aside from the assessment type, client name, address, and key personnel contact information, some other critical pieces of information include:

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.