A penetration tester has gained access to the Chief Executive Officer's (CEO's) internal, corporate email. The next objective is to gain access to the network. Which of the following methods will MOST likely work?
A.
Try to obtain the private key used for S/MIME from the CEO's account.
B.
Send an email from the CEO's account, requesting a new account.
C.
Move laterally from the mail server to the domain controller.
D.
Attempt to escalate privileges on the mail server to gain root access.
B. Send an email from the CEO's account, requesting a new account.
Sending an email from the CEO's account, requesting a new account is a likely method to gain access to the network. This method leverages the trust that is placed in the CEO's account and makes it more likely that the request for a new account will be fulfilled without question. The email can be sent to the IT department or the help desk and request for a new account with high level access. This method is more likely to work as it uses social engineering to trick the IT staff into providing access.
A. Trying to obtain the private key used for S/MIME from the CEO's account is not likely to work as the private key is usually protected by a password and should be kept secret.
C. Moving laterally from the mail server to the domain controller is not likely to work as it requires knowledge of the internal network architecture and may be detected by security controls in place.
D. Attempting to escalate privileges on the mail server to gain root access is not likely to work as it requires knowledge of the mail server software and configuration, and may be detected by security controls in place.
B. Send an email from the CEO’s account, requesting a new account.
Explanation:
• Leveraging Authority: An email from the CEO requesting a new account will likely be acted upon quickly by IT staff due to the perceived urgency and importance of the request.
• Social Engineering: This method takes advantage of social engineering by exploiting the authority and trust associated with the CEO’s position to gain network access.
• Minimal Technical Barriers: Unlike trying to obtain private keys or escalate privileges on the mail server, sending an email request is straightforward and less likely to raise immediate technical red flags.
Need creds to do C.
In case you're neurospicy and take things literal like me, the question is referring to a system acct, not an email acct. Emailing sysadmin for a new account with system access is how you get the creds to move laterally.
Going with B as the human factor is (usually) the easiest to exploit, and the question is which is MOST likely to work, not necessarily the most effective.
B. Send an email from the CEO's account, requesting a new account.
This is a social engineering tactic. By sending an email from the CEO's compromised email account, the penetration tester can attempt to trick an employee with administrative privileges to create a new account for the attacker. This new account would potentially grant the attacker network access, especially if it is granted administrative rights.
The other options do not directly involve leveraging the compromised CEO's email account to gain network access:
A. Trying to obtain the private key used for S/MIME would be a technical effort that may not lead to network access.
C. Moving laterally from the mail server to the domain controller would require further exploitation and may not be directly related to the CEO's email access.
D. Attempting to escalate privileges on the mail server does not necessarily guarantee network access, and it may not be related to using the CEO's compromised email.
Among the given options, C. Move laterally from the mail server to the domain controller is the method that is MOST likely to help in gaining access to the network.
The correct answer is B. Impersonating as the CEO will be deemed a form of authority and social engineering. The other approaches are technical in nature and you should not assume, you have access to the email server. For example, if a company uses Gmail as their mail server, does it make sense to think you'll be able to perform those activities or even O365. Think again. These questions have to be analyzed from all angles. The technical answer isn't always the easiest one. The point is to GAIN access to the network. NOT to GAIN PRIVILEGED access.
This is a poor question because I believe the answer is C due to the fact that we are unsure if the tester is within a known environment or not. Going off the information that we have, you should suspect that the tester has knowledge of the network infrastructure. Since he has access to the CEO's email he should move laterally to the domain controller which would give him access to the network. Thats what the next objective is, not obtain credentials to the network for access. I hate these question because of these persepectives.....
Move laterally from the mail server to the domain controller.
Explanation:
Once a penetration tester gains access to the CEO's internal, corporate email, they can use the information in the emails to perform reconnaissance and identify the mail server used by the organization. The penetration tester can then try to move laterally from the mail server to other systems on the network, such as the domain controller, to gain further access.
I agree with your thinking especially as your objective is to infiltrate the network.
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