You are on an internal test. The corporate firewall blocks all outbound traffic except TCP/443 to a specific set of allowed domains. You need to exfiltrate data to an external server you control. Which technique is most likely to succeed?

Use a domain you control that is not in the allowed list, and send data over HTTPS to that domain.

Use a VPN over HTTPS to a server you control, but the server's domain is not in the allowed list.

Use DNS tunneling to encode data in DNS queries to a domain you control.

Use a domain in the allowed list, such as a popular cloud service, and use a feature like a webhook or storage to exfiltrate data.

You are performing an external penetration test. The target organization's firewall only allows outbound DNS (UDP/TCP 53) and HTTPS (TCP 443) from the internal network. You need to establish a command-and-control channel that will not be blocked. Which technique is most appropriate?

Use HTTP over TCP 80 to a public server.

Use an SSH tunnel over TCP 22 to a public server.

Use DNS tunneling to encapsulate data in DNS queries and responses.

Use ICMP echo requests to tunnel data.

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Perimeter Defense Evasion Techniques CPENT Practice Questions (Page 4)

Part of the Perimeter Evasion and Host Exploitation domain, which makes up ~13% of our current practice bank.

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Questions 16–20

16foundation · easy
A penetration tester wants to bypass a firewall rule that only allows traffic from a specific trusted IP address. Which technique would directly address this restriction?
Select an answer first
17expert · hard
You are on an internal test. The corporate firewall blocks all outbound traffic except TCP/443 to a specific set of allowed domains. You need to exfiltrate data to an external server you control. Which technique is most likely to succeed?
Select an answer first
18application · medium
You are performing an external penetration test. The target organization's firewall only allows outbound DNS (UDP/TCP 53) and HTTPS (TCP 443) from the internal network. You need to establish a command-and-control channel that will not be blocked. Which technique is most appropriate?
Select an answer first
19foundation · easy
Which application-layer evasion technique involves using a commonly allowed protocol, such as HTTP, to carry malicious traffic?
Select an answer first
20foundation · easy
Which IDS/IPS evasion technique relies on the fact that the IDS/IPS and the target host may interpret the same traffic differently?
Select an answer first

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Perimeter Defense Evasion Techniques CPENT Practice Questions (Page 4)

Questions 16–20

A penetration tester wants to bypass a firewall rule that only allows traffic from a specific trusted IP address. Which technique would directly address this restriction?

You are on an internal test. The corporate firewall blocks all outbound traffic except TCP/443 to a specific set of allowed domains. You need to exfiltrate data to an external server you control. Which technique is most likely to succeed?

You are performing an external penetration test. The target organization's firewall only allows outbound DNS (UDP/TCP 53) and HTTPS (TCP 443) from the internal network. You need to establish a command-and-control channel that will not be blocked. Which technique is most appropriate?

Which application-layer evasion technique involves using a commonly allowed protocol, such as HTTP, to carry malicious traffic?

Which IDS/IPS evasion technique relies on the fact that the IDS/IPS and the target host may interpret the same traffic differently?

Keep studying — Perimeter Evasion and Host Exploitation