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Certified Ethical Hacker (CEH) Practice Question

During a penetration test you capture an SMTP session between the organization's mail server and an external partner. After the EHLO exchange you see the command 'STARTTLS' followed by a TLS handshake. Management claims this means all outbound email is now fully encrypted until it reaches recipients. As the consultant, what is the correct explanation?

  • STARTTLS guarantees end-to-end encryption of the message body until it is opened in the recipient's mail client.

  • The command digitally signs each message with the server's certificate, providing authenticity but not confidentiality.

  • It establishes an IPsec ESP tunnel between sender and recipient networks, protecting headers and body throughout transit.

  • The SMTP channel is encrypted only for this hop; without S/MIME or OpenPGP the message can still be stored or forwarded in clear text later.

Certified Ethical Hacker (CEH)
Cryptography
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