Advanced Red

Teaming Interview
Q&A (2025) -
Relevant
Top 29 Questions with Expert
Answers

Author: Dr. Strike

How would you bypass EDR (Endpoint
Detection and Response) solutions like
CrowdStrike or SentinelOne in 2025?

➢ In 2025, I would employ fileless techniques, such as PowerShell-based attacks or

leveraging trusted system processes. I’d also use EDR evasion methods like
timestomping, process injection, and modifying EDR configurations via trusted
signed binaries to bypass detection. Additionally, I’d exploit vulnerabilities in the
EDR itself.
Walk me through developing an initial
foothold in a mature environment
using only OSINT and phishing.

➢ I'd start with OSINT to identify key employees, technologies, and trusted third-
party relationships. Using this intel, I'd craft a highly targeted phishing campaign
with a context-driven pretext and weaponized payload, like HTML smuggling or
MFA fatigue. Post-exploit, I'd maintain stealth using living-off-the-land techniques
to evade detection in a mature environment.
What is your strategy for
conducting a stealthy Active
Directory enumeration?

➢ In 2025, I’d use techniques like DNS enumeration, LDAP enumeration, and
SMB/NetSession scanning to gather domain information stealthily. I’d minimize
footprint with native tools like PowerShell’s Get-ADUser and Net Group.
Additionally, I’d employ techniques like DCOM and WMI for lateral movement,
ensuring low detection.
How do you execute a DNS-based
C2 (Command and Control)
channel that avoids detection?

➢ In 2025, I would use DNS tunneling to encode C2 traffic within DNS queries,
leveraging existing DNS infrastructure for stealth. I’d set up a subdomain for
communication, use randomized subdomain names, and employ encryption like
base64 to obfuscate data. Traffic patterns would be adjusted to mimic normal
DNS traffic to avoid detection.
Discuss evasion techniques
to persist within a Zero Trust
architecture.

➢ In a Zero Trust architecture, persistence relies on evading continuous

authentication checks. I would use lateral movement techniques, exploit
vulnerabilities in trusted endpoints, and abuse misconfigurations in micro-
segmentation. Additionally, I’d manipulate identity providers or hijack sessions
with token replay to maintain stealth and access.
What is your process for conducting a
hybrid attack combining cloud and on-
premises systems?

➢ In a hybrid attack, I’d first compromise on-premises systems using traditional

techniques like phishing or exploitation of legacy vulnerabilities. Next, I’d escalate
privileges and move laterally, gaining access to cloud credentials through cloud
configuration weaknesses or mismanaged IAM policies. I’d then pivot to the cloud,
leveraging both environments for persistence.
Explain how you’d exploit
Kubernetes clusters in a
hardened environment.

➢ In a hardened Kubernetes environment, I’d focus on misconfigurations in RBAC,

weak service account permissions, or exposed API servers. I’d exploit any
vulnerabilities in container runtimes or ingress controllers. I’d also use techniques
like privilege escalation through pod security policies or compromising third-party
integrations for further access.
What are modern techniques
to evade network detection
systems (NDR)?

➢ Modern techniques to evade NDR systems include using encrypted traffic (e.g.,
SSL/TLS), employing traffic obfuscation methods like tunneling over DNS or
HTTPS, and utilizing legitimate network protocols for malicious activities. I’d also
employ evasion through time-based tactics, delaying or spreading malicious
activity to avoid detection during regular traffic analysis.
How would you escalate
privileges on a Linux server
with minimal footprint?

➢ I’d inspect cron jobs and writable scripts, exploit SUID binaries, or manipulate
environmental variables with LD_PRELOAD. If the kernel is vulnerable, I’d use an
exploit like Dirty Pipe (CVE-2022-0847) for root access.
How do you emulate a
ransomware attack in a red
team exercise?

➢ I’d deploy a custom ransomware binary using AES or ChaCha20 for encryption.
Files would be encrypted selectively to simulate impact while ensuring
decryptability post-engagement. For realism, I’d exfiltrate data first, mimicking
double extortion tactics.
How would you breach
an air-gapped network?
➢ I’d use USB drops with payloads or leverage insider threats. For exfiltration, I’d
explore covert channels like RF emissions or manipulate device LEDs. Optical
techniques, like encoding data into screen flashes, could also work.
How do you approach lateral
movement in a hardened
Active Directory environment?

➢ I’d exploit Kerberos delegation issues or trust relationships in multi-forest setups.

Tools like PetitPotam for coercing authentication or abusing Shadow Credentials
are effective in such cases.
How do you perform advanced
credential harvesting in a locked-
down Windows environment?

➢ Using in-memory tools like Mimikatz, I’d extract credentials directly from LSASS via
direct syscalls. I’d also target DPAPI-protected credentials stored locally.
Describe techniques for subverting
security controls during a red team
engagement.

➢ I’d tamper with Sysmon logging by manipulating configuration files, disable EDR
tamper protections stealthily, or patch running processes using reflective DLL
injection.
What is your approach to post-
exploitation in cloud environments
like AWS or Azure?

➢ I’d enumerate IAM roles, identify privilege escalation paths, and abuse serverless
functions for persistence. Misconfigurations in S3 buckets or Azure Blob Storage
would be my exfiltration channels.
How do you use AI in red team
engagements in 2025?

➢ I’d leverage AI for dynamic OSINT, generating polymorphic malware, and analyzing
network data to identify potential attack paths. ML-based payloads adapt to their
environments in real-time.
Explain a method for
exploiting a secure CI/CD
pipeline.

➢ I’d target vulnerable dependencies or inject malicious code into pipeline scripts.
Exploiting misconfigured artifact repositories like JFrog or targeting build agents
with privileged access would be effective
How would you exfiltrate data
in a high-surveillance
network?

➢ Using steganography, I’d hide data within image or audio files sent over permitted
channels. Alternatively, encrypted DNS or HTTPS requests can serve as covert
channels.
Describe how to execute a chain
attack involving OT (Operational
Technology) systems.

➢ I’d breach IT systems first, pivot to OT networks via bridging devices, and then
exploit SCADA protocols like MODBUS to manipulate OT processes.
How would you implement
MFA fatigue as an attack
vector?

➢ I’d repeatedly send push notifications to the target user until they approve one out
of frustration. Simultaneously, I’d combine this with social engineering to make the
victim think it’s a legitimate login attempt.
How do you conduct a covert
data exfiltration over email?

➢ I’d split the data into base64-encoded chunks and send it via encrypted email
attachments or embed the data into draft emails that don’t trigger outbound
monitoring policies.
How would you subvert
threat hunting processes?

➢ I’d inject noise into logs, creating a flood of irrelevant events. I’d also disguise
malicious traffic by mimicking legitimate processes or modify timestamps to
mislead investigators.
What steps would you take
after identifying a zero-day
vulnerability?

➢ I’d analyze the vulnerability’s impact and create a proof-of-concept exploit in a

controlled environment. Depending on the engagement, I’d either responsibly
disclose it or weaponize it for the red team exercise with strict controls.
How do you emulate a nation-
state threat actor in a red
team exercise?

➢ I’d study the TTPs of specific APT groups (e.g., APT29) and replicate their
techniques using similar tools, timing, and communication strategies. Custom
malware or frameworks that mimic their sophistication would be employed.
How would you persist within
a macOS environment?

➢ I’d modify launch agents or daemons for persistence. Additionally, I’d use
AppleScript or deploy malicious kernel extensions that blend into legitimate
system operations.
How would you manipulate
IoT devices for red team
purposes?

➢ I’d exploit weak default credentials or firmware vulnerabilities. Additionally, I’d

inject malicious code during over-the-air (OTA) updates or manipulate device
communication protocols.
How would you evade modern
firewalls like Palo Alto or
Zscaler?

➢ I’d use encrypted tunnels, such as SSH or domain fronting, to bypass inspection.
Masking malicious traffic as legitimate HTTPS traffic or leveraging a trusted
domain for obfuscation would also be effective.
How do you approach
physical red teaming
engagements?

➢ To bypass physical security, I would employ lock-picking tools or RFID cloning to

gain unauthorized access. If those methods fail, I’d bypass security using cloned
badges or access cards. As a last resort, I’d leverage social engineering, such as
posing as maintenance staff, to exploit trust and gain entry.
How do you perform covert
malware delivery in environments
with heavy email filtering?

➢ I’d embed payloads in password-protected ZIP files or Excel sheets using formula-
based payload delivery. Using encrypted outbound links hosted on legitimate
platforms ensures further evasion.