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PT0-002 · Question #222

A penetration tester wants to validate the effectiveness of a DLP product by attempting exfiltration of data using email attachments. Which of the following techniques should the tester select to…

The correct answer is B. Metadata removal. A penetration tester can attempt to exfiltrate data by removing sensitive metadata from email attachments, as some DLP products may fail to inspect or classify files correctly once this information is purged.

Attacks and Exploits

Question

A penetration tester wants to validate the effectiveness of a DLP product by attempting exfiltration of data using email attachments. Which of the following techniques should the tester select to accomplish this task?

Options

  • ASteganography
  • BMetadata removal
  • CEncryption
  • DEncode64

How the community answered

(52 responses)
  • A
    4% (2)
  • B
    71% (37)
  • C
    17% (9)
  • D
    8% (4)

Why each option

A penetration tester can attempt to exfiltrate data by removing sensitive metadata from email attachments, as some DLP products may fail to inspect or classify files correctly once this information is purged.

ASteganography

Steganography involves hiding data within other files, which is a technique for covert exfiltration, but less specifically tied to 'metadata removal' as a test vector for DLP.

BMetadata removalCorrect

Removing metadata from files before sending them as email attachments can bypass DLP products that rely on specific metadata tags or properties for classification or content inspection. This technique changes the file's characteristics, potentially allowing sensitive content to slip past rules focused on specific metadata.

CEncryption

Encryption is a highly effective method to bypass content-based DLP as it makes the data unreadable, but it's a different mechanism than manipulating metadata.

DEncode64

Base64 encoding changes the data representation but does not inherently hide content from modern DLP solutions that are typically capable of decoding common encodings for inspection.

Concept tested: DLP bypass - metadata manipulation

Source: https://learn.microsoft.com/en-us/microsoft-365/compliance/dlp-learn-about-dlp?view=o365-worldwide

Topics

#DLP bypass#Exfiltration techniques#Metadata#Penetration testing

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