312-50V11 · Question #656
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-invalid address triggers a Non-Delivery Report (NDR) that can expose mail server software, version, and internal routing details useful in a penetration test.
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
(51 responses)- A4% (2)
- B16% (8)
- C2% (1)
- D71% (36)
- E8% (4)
Why each option
Sending email to a known-invalid address triggers a Non-Delivery Report (NDR) that can expose mail server software, version, and internal routing details useful in a penetration test.
Bounce messages reveal MTA and routing information, not the identity of the root account holder.
Sending a single email to an invalid address does not generate enough load to constitute a denial-of-service attack.
The goal is targeted intelligence gathering about the mail server, not generating unsolicited bulk mail.
When an SMTP server receives mail for a non-existent recipient, it returns a bounce or NDR message. This error response often contains the mail transfer agent (MTA) name, version number, internal hostnames, and relay paths - intelligence that helps a penetration tester map the email infrastructure and identify exploitable software versions.
Virus protection testing requires sending a known-malicious or EICAR test file as an attachment, not an undeliverable address.
Concept tested: SMTP banner and NDR information disclosure during reconnaissance
Source: https://learn.microsoft.com/en-us/exchange/mail-flow-best-practices/non-delivery-reports-in-exchange-online/non-delivery-reports-in-exchange-online
Topics
Community Discussion
No community discussion yet for this question.