INTERVIEW QUESTION TIPS – PENTEST, RED

TEAM, APPSEC AND BLUE TEAM

Joas A Santos
https://www.linkedin.com/in/joas-antonio-dos-santos
PenTest Questions
Question: How do you begin scoping a penetration testing engagement?
Answer:
Step 1: Understand the client's objectives and expectations.
Step 2: Identify the target systems, applications, and networks.
Step 3: Establish the boundaries and limitations of the test.
Step 4: Determine the testing methodology and tools to be used.
Step 5: Create a timeline for the engagement, including milestones and
deliverables.
Step 6: Develop a communication plan with the client.

Question: What steps do you follow when performing reconnaissance?

Answer:
Step 1: Passive information gathering (OSINT) – collect information on the target
using public sources.
Step 2: Active information gathering – interact with the target system or network
to collect information.
Step 3: Identify the target's network topology.
Step 4: Enumerate services, open ports, and running applications.
Step 5: Identify potential vulnerabilities by mapping collected information.

Question: How do you perform a vulnerability assessment?

Answer:
Step 1: Identify the assets and prioritize them based on their criticality.
Step 2: Perform a comprehensive scan using automated tools like Nessus or
OpenVAS.
Step 3: Manually validate the identified vulnerabilities.
Step 4: Analyze the findings and determine their impact.
Step 5: Document the vulnerabilities and provide recommendations for
remediation.

Question: Describe your approach to exploiting a web application.

Answer:
Step 1: Identify the web application's technology stack.
Step 2: Fingerprint the application to discover versions and configurations.
Step 3: Analyze the application's functionality and identify potential attack
vectors.
Step 4: Test for common web application vulnerabilities such as SQL injection,
XSS, and CSRF.
Step 5: Exploit discovered vulnerabilities using manual and automated tools.
Step 6: Document findings, provide proof of concept, and suggest remediation
measures.

Question: How do you maintain persistence during a penetration test?

Answer:
Step 1: Identify an entry point that allows for long-term access.
Step 2: Create a backdoor, such as a reverse shell, to maintain control.
Step 3: Employ techniques to evade detection by security systems.
Step 4: Periodically update and modify the backdoor to avoid discovery.
Step 5: Set up an alternative access point as a backup.

Question: What steps do you take to cover your tracks during a penetration test?
Answer:
Step 1: Use proxy servers, VPNs, or TOR to hide your IP address.
Step 2: Employ anti-forensic techniques to avoid leaving traces.
Step 3: Clear log files and system artifacts.
Step 4: Delete or modify any evidence of the penetration test.
Step 5: Use encryption and steganography to hide data.

Question: How do you manage and report the findings of a penetration test?
Answer:
Step 1: Organize findings by priority, impact, and risk level.
Step 2: Prepare detailed documentation of the discovered vulnerabilities.
Step 3: Provide proof of concept for exploited vulnerabilities.
Step 4: Offer recommendations for remediation and mitigation.
Step 5: Present the report to the client and discuss the findings.

Question: How do you stay current with the latest penetration testing tools and
techniques?
Answer:
Step 1: Regularly read cybersecurity blogs and news sources.
Step 2: Follow industry leaders and experts on social media.
Step 3: Participate in online forums and discussion boards.
Step 4: Attend conferences, workshops, and webinars.
Step 5: Engage in continuous learning through certifications and training courses.

Question: How do you prioritize vulnerabilities during a penetration test?

Step 1: The impact of each vulnerability on the target system or organization.
Step 2: Evaluate the likelihood of exploitation based on the complexity of the
vulnerability and the attacker's skill level.
Step 3: Consider the target's criticality, such as the importance of data or
functionality it supports.
Step 4: Take into account any existing security controls that may mitigate the risk.
Step 5: Rank the vulnerabilities based on the overall risk they pose, prioritizing
those with the highest potential impact and likelihood of exploitation.
Question: How do you handle a situation where you accidentally cause damage or
disruption during a penetration test?
Answer:
Step 1: Immediately halt the testing activity that caused the issue.
Step 2: Assess the extent of the damage or disruption.
Step 3: Inform the client or relevant stakeholders about the incident and its
impact.
Step 4: Work with the client to develop a plan for mitigating the damage or
restoring the affected systems or services.
Step 5: Analyze the incident to identify the root cause and prevent similar issues
in future engagements.
Step 6: Document the incident and any lessons learned as part of the penetration
test report.
Red Team Questions
Question: How do you plan and execute an adversary emulation exercise?
Answer:
Step 1: Research the targeted organization and its typical adversaries.
Step 2: Create a realistic threat profile based on known TTPs (Tactics, Techniques,
and Procedures) of the chosen adversary.
Step 3: Develop a detailed emulation plan, including objectives, timeline, and
expected outcomes.
Step 4: Collaborate with the organization's Blue Team to establish rules of
engagement and communication protocols.
Step 5: Execute the emulation, following the plan and adapting as necessary.
Step 6: Analyze the results and provide feedback to improve the organization's
security posture.

Question: How do you establish command and control (C2) during a Red Team
engagement?
Answer:
Step 1: Identify potential C2 channels, such as HTTP, DNS, or social media.
Step 2: Select a suitable C2 framework, like Cobalt Strike or Empire, based on the
target environment and objectives.
Step 3: Deploy the C2 infrastructure, ensuring redundancy and resilience.
Step 4: Implement techniques to bypass security controls and avoid detection.
Step 5: Establish a connection between the compromised host and the C2 server.
Step 6: Maintain control and communication throughout the engagement.

Question: How do you design and set up a resilient C2 infrastructure for a Red
Team operation?
Answer:
Step 1: Choose a suitable hosting provider and domain registrar to establish the
C2 server and domain.
Step 2: Implement domain fronting or use a Content Delivery Network (CDN) to
obscure the C2 server's true location.
Step 3: Set up multiple C2 servers and domains for redundancy and failover.
Step 4: Use SSL certificates and encryption to secure communications between
the C2 server and compromised hosts.
Step 5: Regularly update the infrastructure to avoid detection by security tools
and systems.

Question: How do you use Windows API functions to perform tasks during a Red
Team engagement?
Answer:
Step 1: Research the relevant Windows API functions required to achieve the
desired outcome.
Step 2: Write code, such as in C++ or C#, that leverages the identified Windows
API functions.
Step 3: Compile the code into an executable or a dynamic-link library (DLL).
Step 4: Test the resulting binary in a controlled environment to ensure proper
functionality and avoid detection.
Step 5: Deploy and execute the binary on the target system during the
engagement.
Question: How do you conduct an initial compromise in a Windows environment
during a Red Team operation?
Answer:
Step 1: Perform reconnaissance to gather information on the target environment.
Step 2: Identify potential attack vectors, such as phishing, social engineering, or
exploiting known vulnerabilities.
Step 3: Develop and customize a payload or exploit that is compatible with the
target environment.
Step 4: Execute the initial compromise using the chosen attack vector.
Step 5: Establish a foothold in the environment by gaining persistence and
establishing C2 communications.

Question: How do you achieve persistence in a Windows environment during a

Red Team operation?
Answer:
Step 1: Identify potential persistence mechanisms, such as scheduled tasks,
services, or registry modifications.
Step 2: Evaluate the target environment for the most suitable persistence method
based on detection risk and required privileges.
Step 3: Implement the chosen persistence method using tools, scripts, or custom
code.
Step 4: Test the persistence mechanism to ensure it remains functional after
system reboots or user logouts.
Step 5: Monitor the persistence mechanism for potential detection and adapt as
necessary.
Question: How do you perform lateral movement in a Windows environment
during a Red Team operation?
Answer:
Step 1: Enumerate the target network to identify systems, users, and resources.
Step 2: Gather credentials, tokens, or other authentication material through
techniques like password dumping, keylogging, or Mimikatz.
Step 3: Identify potential lateral movement techniques, such as Pass-the-Hash,
Pass-the-Ticket, or remote code execution.
Step 4: Select the most suitable technique based on the target environment,
access level, and detection risk.
Step 5: Execute the chosen lateral movement technique to compromise
additional systems and further infiltrate the network.

Question: How do you perform privilege escalation in a Windows environment

during a Red Team operation?
Answer:
Step 1: Enumerate the target system to identify potential vulnerabilities,
misconfigurations, or weak security controls.
Step 2: Research known privilege escalation techniques or exploits that may be
applicable to the target environment.
Step 3: Evaluate the feasibility of each technique based on the available access
level and detection risk.
Step 4: Execute the chosen privilege escalation technique to gain higher-level
privileges, such as local administrator or domain administrator.
Step 5: Validate the successful privilege escalation and leverage the elevated
access for further operations.

Question: How do you maintain operational security during a Red Team operation
in a Windows environment?
Answer:
Step 1: Use obfuscation and encryption techniques to hide the true nature of
payloads, communication, and tools.
Step 2: Employ anti-forensic techniques to minimize traces left on compromised
systems.
Step 3: Leverage built-in Windows tools and functionality whenever possible to
blend in with normal system activity.
Step 4: Monitor the target environment for indications of detection or response,
and adapt operations as needed.
Step 5: Conduct periodic reviews of operational security and make necessary
adjustments to maintain stealth.

Question: How do you exfiltrate data from a Windows environment during a Red
Team operation?
Answer:
Step 1: Identify the target data based on the engagement objectives and the
organization's critical assets.
Step 2: Collect and consolidate the data from various systems and storage
locations.
Step 3: Apply encryption or steganography techniques to secure and obscure the
data.
Step 4: Choose an exfiltration method, such as transferring the data over an
encrypted C2 channel or using a third-party cloud storage service.
Step 5: Execute the chosen exfiltration method and monitor the process to ensure
successful data transfer and avoid detection.
APPSEC Question
Question: Describe the process for identifying and correcting application
vulnerabilities.
Answer:
Step 1: Perform regular vulnerability assessments using tools such as automated
scanners, code analyzers, or manual reviews.
Step 2: Analyze the results to identify potential vulnerabilities and their root
causes.
Step 3: Prioritize vulnerabilities based on their potential impact, likelihood of
exploitation, and the affected application's criticality.
Step 4: Develop and implement fixes or mitigations for the identified
vulnerabilities.
Step 5: Test the corrections to ensure they effectively address the vulnerabilities
without introducing new issues.
Step 6: Monitor the application for any new or recurring vulnerabilities and
continuously improve the security posture.

Question: How do you use OWASP resources to improve the security of an

application?
Answer:
Step 1: Familiarize yourself with the OWASP Top Ten Project, which outlines the
most critical web application security risks.
Step 2: Leverage the OWASP Application Security Verification Standard (ASVS) as
a guide for secure application development.
Step 3: Use the OWASP Cheat Sheet Series to access concise guidance on specific
application security topics.
Step 4: Employ OWASP testing methodologies, such as the OWASP Web
Application Penetration Testing Methodology, to assess the application's security.
Step 5: Integrate OWASP tools, such as ZAP or Dependency-Check, into the
development and testing processes.
Step 6: Keep up to date with the latest OWASP projects and resources to maintain
awareness of emerging threats and best practices.
Question: How do you implement the OWASP Software Assurance Maturity
Model (SAMM) in your organization?
Answer:
Step 1: Assess the current state of your organization's software assurance
practices.
Step 2: Select the relevant SAMM maturity level and security practice areas based
on your organization's needs and goals.
Step 3: Define the objectives and activities required to achieve the desired
maturity level.
Step 4: Develop a roadmap and timeline for implementing the chosen SAMM
activities.
Step 5: Train and educate the team on the SAMM framework and the specific
activities involved.
Step 6: Regularly review and measure the progress towards the desired maturity
level and adapt the implementation plan as needed.
Question: How do you conduct threat modeling for an application?
Answer:
Step 1: Define the application's scope, architecture, and components.
Step 2: Identify the application's assets, such as sensitive data or critical
functionality.
Step 3: Determine potential threats to the application by considering factors such
as threat actors, attack vectors, and vulnerabilities.
Step 4: Assess the likelihood and impact of each threat to prioritize them.
Step 5: Develop and implement mitigations or controls to address the identified
threats.
Step 6: Review and update the threat model periodically or when significant
changes are made to the application.
Question: How do you address the OWASP Top Ten risks in your application?
Answer:
Step 1: Review the OWASP Top Ten list and understand the associated risks and
vulnerabilities.
Step 2: Assess your application for potential vulnerabilities related to each of the
Top Ten risks.
Step 3: Prioritize the identified vulnerabilities based on their potential impact and
likelihood of exploitation.
Step 4: Implement security controls and best practices to mitigate the risks, such
as input validation, secure coding, and encryption.
Step 5: Regularly test your application for vulnerabilities, including those in the
OWASP Top Ten, using vulnerability assessments and penetration testing.
Step 6: Continuously monitor and update the application to address any new or
recurring risks associated with the OWASP Top Ten.
Question: How do you ensure secure coding practices within your development
team?
Answer:
Step 1: Develop and implement secure coding guidelines
Step 2: Train developers on secure coding principles, including common
vulnerabilities, attack vectors, and best practices.
Step 3: Integrate security tools, such as static application security testing (SAST)
and dynamic application security testing (DAST), into the development process.
Step 4: Perform regular code reviews to identify and correct potential security
issues.
Step 5: Foster a culture of security within the development team by promoting
collaboration and communication around security topics.
Step 6: Continuously update the secure coding guidelines and training based on
new threats, technologies, and industry standards
Question: How do you manage third-party components and their security risks in
an application?
Answer:
Step 1: Maintain an inventory of all third-party components used within the
application, including libraries, frameworks, and APIs.
Step 2: Assess the security posture of each component by researching known
vulnerabilities, historical issues, and vendor reputation.
Step 3: Continuously monitor for newly disclosed vulnerabilities or security
advisories related to the components.
Step 4: Apply patches or updates to the components as needed to address known
vulnerabilities.
Step 5: Limit the use of unnecessary or risky components by implementing a
component approval process.
Step 6: Evaluate alternative components or solutions if the security risks
associated with a particular component are deemed too high.
Question: How do you protect an application against SQL injection attacks?
Answer:
Step 1: Implement input validation to ensure user-supplied data adheres to
expected formats and constraints.
Step 2: Utilize prepared statements or parameterized queries to separate user
data from SQL commands.
Step 3: Employ least privilege access controls for database accounts, limiting the
potential impact of an attack.
Step 4: Regularly review and update database configurations and settings to
minimize potential vulnerabilities.
Step 5: Test the application for SQL injection vulnerabilities using techniques such
as fuzz testing, penetration testing, or automated scanning tools.
Step 6: Monitor application logs and database activity for signs of potential SQL
injection attacks.
Question: How do you protect an application against Cross-Site Scripting (XSS)
attacks?
Answer:
Step 1: Implement input validation to ensure user-supplied data adheres to
expected formats and constraints.
Step 2: Encode or sanitize user-supplied data before displaying it within the
application to prevent the execution of malicious scripts.
Step 3: Utilize secure coding practices, such as escaping or validating dynamic
content, to reduce the likelihood of introducing XSS vulnerabilities.
Step 4: Apply Content Security Policy (CSP) headers to limit the sources and types
of scripts that can be executed within the application.
Step 5: Test the application for XSS vulnerabilities using techniques such as
penetration testing or automated scanning tools.
Step 6: Monitor application logs and user activity for signs of potential XSS
attacks.

Question: How do you ensure the confidentiality and integrity of sensitive data in
an application?
Answer:
Step 1: Identify and classify sensitive data within the application, such as personal
information, credentials, or payment data.
Step 2: Implement data encryption, both in transit and at rest, using industry-
standard encryption algorithms and key management practices.
Step 3: Employ access controls and authentication mechanisms to limit access to
sensitive data based on the principle of least privilege.
Step 4: Utilize secure coding practices and input validation to prevent data
leakage or tampering through vulnerabilities, such as injection attacks or insecure
direct object references.
Step 5: Conduct regular security assessments, such as vulnerability scanning and
penetration testing, to identify potential risks to sensitive data.
Step 6: Monitor application logs and user activity to detect and respond to
potential data breaches or unauthorized access.

Blue Team Question

Question: Describe the incident response process and the key steps involved.
Answer:
Step 1: Preparation - Develop and maintain an incident response plan, including
roles, responsibilities, and communication protocols.
Step 2: Detection and Analysis - Identify potential security incidents by monitoring
logs, alerts, and reports from security tools.
Step 3: Containment - Isolate the affected systems or networks to prevent further
damage or spread of the incident.
Step 4: Eradication - Remove the threat from the affected systems or networks
and restore them to a secure state.
Step 5: Recovery - Return the affected systems or networks to normal operations,
ensuring they are secure and fully functional.
Step 6: Lessons Learned - Analyze the incident, document findings, and
implement improvements to prevent future incidents.

Question: How do you integrate threat intelligence into your organization's

security operations?
Answer:
Step 1: Identify relevant threat intelligence sources, such as commercial feeds,
open-source platforms, and industry partnerships.
Step 2: Collect and aggregate the threat intelligence data.
Step 3: Analyze and prioritize the data based on its relevance, impact, and
timeliness.
Step 4: Integrate the threat intelligence into security tools and processes, such as
SIEM platforms or intrusion detection systems.
Step 5: Disseminate the threat intelligence to relevant stakeholders within the
organization.
Step 6: Continuously monitor and update threat intelligence feeds to stay current
with emerging threats.

Question: What is the process for conducting a threat hunting operation?

Answer:
Step 1: Develop a hypothesis based on threat intelligence, past incidents, or
known attack patterns.
Step 2: Gather data from various sources, such as logs, network traffic, or
endpoint telemetry.
Step 3: Analyze the data using automated tools and manual techniques to identify
patterns or anomalies.
Step 4: Investigate any findings to determine if they represent a potential threat
or security incident.
Step 5: Document and communicate the findings, including any recommended
mitigation or remediation actions.
Step 6: Refine and iterate the threat hunting process based on lessons learned
and evolving threats.

Question: How do you perform digital forensics on a compromised system?

Answer:
Step 1: Preserve the evidence by creating a forensic image of the affected system
or device.
Step 2: Isolate the system or device to prevent any further damage or tampering.
Step 3: Analyze the forensic image using specialized tools and techniques to
uncover artifacts, such as files, logs, or registry entries.
Step 4: Recover and examine any deleted or hidden data.
Step 5: Document the findings, including a timeline of events and details about
the compromise.
Step 6: Present the findings to relevant stakeholders and assist with any legal or
regulatory proceedings.

Question: How do you detect and analyze potential malware during an incident
response?
Answer:
Step 1: Collect potential malware samples from the affected systems or network.
Step 2: Perform static analysis on the samples, such as examining file headers,
strings, or hashes.
Step 3: Conduct dynamic analysis by executing the malware in a controlled
environment, such as a sandbox or virtual machine.
Step 4: Analyze the malware's behavior, network activity, and persistence
mechanisms.
Step 5: Identify any indicators of compromise (IOCs) or patterns associated with
the malware.
Step 6: Use the analysis results to inform remediation efforts and update security
controls to prevent future infections.
Question: How do you prioritize incidents during incident response?
Answer:
Step 1: Assess the potential impact of the incident on the organization's
operations, reputation, or regulatory compliance.
Step 2: Determine the scope of the incident, including the number of affected
systems or users.
Step 3: Evaluate the potential risk of data loss, theft, or unauthorized access.
Step 4: Consider the complexity of the incident and the resources required to
address it.
Step 5: Analyze the current and potential future damage caused by the incident.
Step 6: Prioritize incidents based on their overall impact, risk, and resource
requirements, focusing on those with the highest potential for harm or disruption.

Question: How do you validate the effectiveness of security controls during a Blue
Team engagement?
Answer:
Step 1: Identify the security controls in place, such as firewalls, intrusion detection
systems, or access controls.
Step 2: Review the configuration and settings of each control to ensure they align
with best practices and organizational policies.
Step 3: Conduct regular testing, such as vulnerability scans or penetration tests, to
evaluate the effectiveness of the controls.
Step 4: Monitor the performance and alerts generated by the controls to identify
any gaps or weaknesses.
Step 5: Analyze incident response and threat hunting findings to determine if
controls are effective at preventing or detecting threats.
Step 6: Continuously review and update the security controls based on evolving
threats and changing organizational requirements.

Question: How do you create and maintain an effective incident response plan?
Answer:
Step 1: Develop a comprehensive plan that outlines roles, responsibilities, and
procedures for responding to security incidents.
Step 2: Identify key stakeholders and establish communication channels for
reporting and discussing incidents.
Step 3: Define the criteria for classifying and prioritizing incidents based on their
impact and risk.
Step 4: Document incident response procedures, including detection,
containment, eradication, recovery, and lessons learned.
Step 5: Train employees on their roles and responsibilities within the incident
response plan.
Step 6: Regularly review and update the plan based on lessons learned from
previous incidents, changes in the threat landscape, or organizational growth.

Question: How do you perform a root cause analysis during a security incident?
Answer:
Step 1: Gather relevant data, such as logs, network traffic, or forensic artifacts,
from the affected systems or network.
Step 2: Analyze the data to identify patterns, anomalies, or indicators of
compromise.
Step 3: Investigate the findings to trace the sequence of events that led to the
incident.
Step 4: Identify the underlying factors that contributed to the incident, such as
vulnerabilities, misconfigurations, or human error.
Step 5: Determine the root cause of the incident by isolating the primary factor
that allowed the compromise to occur.
Step 6: Document the root cause analysis and use the findings to inform
remediation efforts and improve security controls.

Question: How do you proactively search for signs of compromise within your
organization's environment?
Answer:
Step 1: Develop a baseline understanding of normal system and network
behavior.
Step 2: Use threat intelligence to identify known indicators of compromise (IOCs)
associated with specific threats or threat actors.
Step 3: Monitor logs, network traffic, and endpoint telemetry for anomalies or
deviations from the baseline.
Step 4: Leverage automated tools, such as SIEM platforms or intrusion detection
systems, to flag potential indicators of compromise.
Step 5: Conduct regular threat hunting operations to proactively search for signs
of compromise based on threat intelligence, past incidents, or known attack
patterns.
Step 6: Investigate any identified signs of compromise to determine if they
represent a security incident and initiate the incident response process if
necessary.