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EC-Council

312-50V9 · Question #558

Why would you consider sending an email to an address that you know does not exist within the company you are performing a Penetration Test for?

The correct answer is D. To illicit a response back that will reveal information about email servers and how they treat. Sending email to a known non-existent address triggers a bounce or Non-Delivery Report from the mail server, which can expose server software, version, and internal routing details useful for reconnaissance.

Footprinting and Reconnaissance

Question

Why would you consider sending an email to an address that you know does not exist within the company you are performing a Penetration Test for?

Options

  • ATo determine who is the holder of the root account
  • BTo perform a DoS
  • CTo create needless SPAM
  • DTo illicit a response back that will reveal information about email servers and how they treat
  • ETo test for virus protection

How the community answered

(41 responses)
  • A
    2% (1)
  • B
    2% (1)
  • C
    15% (6)
  • D
    73% (30)
  • E
    7% (3)

Why each option

Sending email to a known non-existent address triggers a bounce or Non-Delivery Report from the mail server, which can expose server software, version, and internal routing details useful for reconnaissance.

ATo determine who is the holder of the root account

NDR responses reveal mail server software and routing metadata, not account ownership information such as who holds the root or administrator account.

BTo perform a DoS

A single bounce-inducing email does not constitute a Denial of Service attack because it generates only one reply message and does not exhaust server resources.

CTo create needless SPAM

The action is deliberate targeted reconnaissance generating one bounce message, not unsolicited bulk email distribution that would qualify as spam.

DTo illicit a response back that will reveal information about email servers and how they treatCorrect

Mail Transfer Agents generate NDR messages when a recipient address is invalid, and these bounce messages commonly include the mail server software name, version, internal IP addresses, and SMTP banner information that a penetration tester can use to fingerprint the email infrastructure.

ETo test for virus protection

Antivirus scanning is triggered by attachment content or known malicious signatures, not by the act of sending to an invalid recipient address.

Concept tested: Email server information disclosure via NDR bounce messages

Source: https://owasp.org/www-project-web-security-testing-guide/latest/4-Web_Application_Security_Testing/07-Input_Validation_Testing/10-Testing_for_IMAP_SMTP_Injection

Topics

#email enumeration#SMTP reconnaissance#bounce messages#information disclosure

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