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SY0-501 · Question #531

Confidential emails from an organization were posted to a website without the organization's knowledge. Upon investigation, it was determined that the emails were obtained from an internal actor who…

The correct answer is C. S/MIME D. SMTPS. An internal actor sniffed plaintext emails, meaning the email transmission lacked encryption. Implementing email-specific encryption protocols would have protected the content from being intercepted in readable form.

Submitted by skyler.x· Mar 4, 2026General security concepts

Question

Confidential emails from an organization were posted to a website without the organization's knowledge. Upon investigation, it was determined that the emails were obtained from an internal actor who sniffed the emails in plain text. Which of the following protocols, if properly implemented, would have MOST likely prevented the emails from being sniffed? (Select TWO)

Options

  • ASecure IMAP
  • BDNSSEC
  • CS/MIME
  • DSMTPS
  • EHTTPS

How the community answered

(38 responses)
  • A
    13% (5)
  • B
    8% (3)
  • C
    76% (29)
  • E
    3% (1)

Why each option

An internal actor sniffed plaintext emails, meaning the email transmission lacked encryption. Implementing email-specific encryption protocols would have protected the content from being intercepted in readable form.

ASecure IMAP

Secure IMAP (IMAP over TLS) protects the retrieval of emails from a mail server to a client, but does not protect emails during the SMTP transmission phase where sniffing likely occurred.

BDNSSEC

DNSSEC provides integrity and authenticity for DNS records by digitally signing DNS responses, but does not encrypt email content or email transmission channels in any way.

CS/MIMECorrect

S/MIME (Secure/Multipurpose Internet Mail Extensions) provides end-to-end encryption and digital signing of email messages, meaning the message body is encrypted at the client level before transmission, so even if sniffed in transit or at rest, the content remains unreadable without the recipient's private key.

DSMTPSCorrect

SMTPS (SMTP Secure) encrypts the SMTP connection using TLS/SSL, protecting email data as it travels between mail servers or from client to server, which would have prevented a network-level sniffing attack from capturing plaintext email content.

EHTTPS

HTTPS encrypts web-based HTTP traffic between a browser and a web server, but does not apply to email protocols such as SMTP, IMAP, or POP3 used for sending and receiving emails.

Concept tested: Email encryption protocols preventing plaintext sniffing

Source: https://learn.microsoft.com/en-us/exchange/policy-and-compliance/smime/smime?view=exchserver-2019

Topics

#S/MIME#SMTPS#email security#encryption protocols

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