hardMultiple ChoiceObjective-mapped
CISSP Practice Question: Implements a data loss prevention (DLP) solution…
An organization implements a data loss prevention (DLP) solution to monitor data in motion. Which type of data is typically most challenging to detect?
⚠ Common exam trap
It's easy for candidates to assume 'data in images' is hardest because it is non-textual, but DLP can use OCR and image analysis, whereas encrypted traffic is fundamentally opaque without decryption keys.
Answer choices
Why each option matters
Answer the question above first, then reveal the full breakdown to understand why each option is right or wrong.
Correct answer & explanation
✓
Encrypted traffic
Encrypted traffic is the most challenging data in motion for DLP to inspect because the payload is obfuscated by encryption protocols such as TLS 1.3 or IPsec. Without decryption (e.g., via a proxy with TLS interception), the DLP sensor cannot read the content to match patterns or keywords, rendering traditional deep packet inspection ineffective.
Answer analysis
Option-by-option breakdown
For each option: why learners choose it and why it is or isn't the right answer here.
- ✗
Data in images
Why it's wrong here
DLP solutions can effectively detect sensitive data embedded within images. Optical Character Recognition (OCR) technology allows DLP to extract and analyze text from image files, applying policies to the recognized content. Furthermore, advanced DLP systems can employ steganalysis techniques to identify and prevent the exfiltration of data hidden covertly within image files, making this a manageable detection scenario.
- ✗
Structured data in CSV files
Why it's wrong here
Structured data, such as that typically found in CSV files, is among the easiest for DLP solutions to detect and enforce policies upon. DLP systems leverage precise pattern matching, regular expressions, and database fingerprinting to accurately identify specific data types like credit card numbers, social security numbers, or proprietary identifiers, ensuring high detection efficacy.
- ✓
Encrypted traffic
Why this is correct
Encrypted network traffic poses the most significant challenge for Data Loss Prevention solutions because the content payload is intentionally obscured, preventing direct inspection. To analyze sensitive information within encrypted streams, DLP typically requires a man-in-the-middle (MITM) proxy to decrypt, inspect, and then re-encrypt the traffic, which introduces complexity, performance overhead, and potential privacy concerns, making it difficult to achieve full content visibility without explicit interception.
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Unstructured data in email attachments
Why it's wrong here
While unstructured data in email attachments, such as documents or presentations, is more complex than structured data, modern DLP solutions are well-equipped to analyze it. They utilize advanced techniques like keyword matching, conceptual analysis, natural language processing (NLP), and machine learning to identify sensitive information, ensuring that policies can be applied effectively even to free-form text.
Quick reference
VPN Protocol Comparison
| Protocol | Port | Encryption | Authentication | Use Case |
|---|---|---|---|---|
| IKEv2 / IPsec | UDP 500 / 4500 | AES-256 | Certificates / PSK | Site-to-site & remote access |
| SSL / TLS VPN | TCP 443 | TLS 1.3 | Certificates / MFA | Clientless remote access |
| L2TP / IPsec | UDP 1701 | AES (IPsec) | PSK / Certificates | Legacy remote access |
| WireGuard | UDP 51820 | ChaCha20 | Public keys | Modern high-performance VPN |
| PPTP | TCP 1723 | MPPE (weak) | MS-CHAPv2 | Legacy — avoid in production |
PPTP is considered insecure. IKEv2/IPsec and SSL VPN are the current recommended options.
Go deeper
Related to this question
Learn chapter
Asset Security: Privacy and Data Retention
Key term
Encryption
Encryption is the process of converting readable data into a secret code to prevent unauthorized access.
Key term
IPsec
IPsec is a suite of protocols used to secure Internet Protocol (IP) communications by encrypting and authenticating each IP packet in a data stream.
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JA
Written by Johnson Ajibi, MSc IT Security
Senior Network & Security Engineer · founder of Courseiva
This CISSP practice question is part of Courseiva's free ISC2 certification practice question bank. Courseiva provides original exam-style practice questions with explanations, topic-based practice, mock exams, readiness tracking, and study analytics to help learners prepare for the CISSP exam.