350-701 Content Security Practice Question
An organization using Cisco WSA in transparent proxy mode with WCCP redirect notices that some HTTPS traffic is not being decrypted for inspection. The administrator has enabled SSL decryption but certain traffic still bypasses. What is the most likely cause?
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
✓
The SSL decryption policy is not set to decrypt on port 443
In transparent proxy mode, SSL decryption requires that the WSA is positioned in the traffic path (e.g., via WCCP). If decryption is not happening, the WSA may not be intercepting the traffic correctly, often due to the destination port not being included in the decryption policy or the traffic being non-HTTP.
Answer analysis
Option-by-option breakdown
For each option: why learners choose it and why it is or isn't the right answer here.
- ✗
The clients are not configured to use a proxy
Why it's wrong here
In transparent mode, clients do not need proxy configuration; traffic is redirected via WCCP.
- ✗
The web server certificate is self-signed
Why it's wrong here
Self-signed certificates can be decrypted; they generate warnings but do not prevent decryption.
- ✗
The WSA is operating in explicit proxy mode
Why it's wrong here
The scenario states transparent mode, so this is not the issue.
- ✓
The SSL decryption policy is not set to decrypt on port 443
Why this is correct
HTTPS traffic typically uses port 443. If the decryption policy does not include port 443, it will not be decrypted.
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Written by Johnson Ajibi, MSc IT Security
Senior Network & Security Engineer · founder of Courseiva
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