- A
HTTPS decryption is disabled globally or for the specific category.
If decryption is disabled, the WSA does not generate certificates; it tunnels the HTTPS traffic without inspection, which should still work unless proxy settings are misconfigured.
- B
The website uses certificate pinning, which prevents interception.
Why wrong: While certificate pinning can cause issues, it would not prevent the WSA from generating a certificate; it would cause a browser warning.
- C
The WSA CA certificate is not installed in the user's browser trust store.
Why wrong: Missing CA certificate would cause a warning, not prevent the WSA from generating a certificate.
- D
The WSA is configured to bypass decryption for the user's subnet.
Why wrong: Bypassing decryption means the WSA does not generate a certificate, but the user should still be able to connect directly through the proxy.
350-701 Content Security Practice Question
This 350-701 practice question tests your understanding of content security. The scenario asks you to isolate a root cause — eliminate options that address a different problem before choosing. After answering, compare your reasoning against the explanation and wrong-answer breakdown below. Once you have made your selection, read the full explanation to reinforce the concept and understand why each distractor is designed to mislead on exam day.
A company uses Cisco Web Security Appliance (WSA) in explicit proxy mode. Users report that some HTTPS websites fail to load. The administrator checks the logs and sees that the WSA is not generating any certificate for those sites. What is the most likely cause?
Clue words in this question
Noticing these words before you look at the options changes how you read each choice.
Clue:
"most likely"Why it matters: Probability qualifier — the question wants the most probable cause or outcome, not a guaranteed one. Eliminate low-probability options.
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
HTTPS decryption is disabled globally or for the specific category.
When HTTPS decryption is disabled globally or for a specific category, the WSA cannot generate a certificate to intercept and inspect the traffic. In explicit proxy mode, the WSA must decrypt HTTPS traffic to apply security policies; without decryption enabled, the proxy simply forwards the traffic without generating a certificate, causing the browser to fail to establish a secure connection for sites that require inspection.
Key principle: Answer the scenario, not the keyword: identify the specific constraint before choosing the most familiar-sounding option.
Answer analysis
Option-by-option breakdown
For each option: why learners choose it and why it is or isn't the right answer here.
- ✓
HTTPS decryption is disabled globally or for the specific category.
Why this is correct
If decryption is disabled, the WSA does not generate certificates; it tunnels the HTTPS traffic without inspection, which should still work unless proxy settings are misconfigured.
Clue confirmation
The clue word "most likely" in the question point toward this answer.
Related concept
Read the scenario before looking for a memorised answer.
- ✗
The website uses certificate pinning, which prevents interception.
Why it's wrong here
While certificate pinning can cause issues, it would not prevent the WSA from generating a certificate; it would cause a browser warning.
- ✗
The WSA CA certificate is not installed in the user's browser trust store.
Why it's wrong here
Missing CA certificate would cause a warning, not prevent the WSA from generating a certificate.
- ✗
The WSA is configured to bypass decryption for the user's subnet.
Why it's wrong here
Bypassing decryption means the WSA does not generate a certificate, but the user should still be able to connect directly through the proxy.
Common exam traps
Common exam trap: answer the scenario, not the keyword
Cisco often tests the distinction between 'no certificate generated' (indicating decryption is disabled) versus 'certificate error' (indicating trust issues or pinning), so candidates mistakenly choose options related to certificate trust or pinning when the core issue is that decryption is simply not enabled.
Detailed technical explanation
How to think about this question
In explicit proxy mode, the WSA acts as a man-in-the-middle for HTTPS traffic by dynamically generating a certificate signed by its own CA for each requested site. If HTTPS decryption is disabled, the WSA cannot perform this interception and instead forwards the CONNECT request without generating a certificate, causing the browser to fail when the site requires a proxy to present a valid certificate. This behavior is controlled by the 'HTTPS Proxy' settings in the WSA GUI, where administrators can enable or disable decryption globally or per URL category.
KKey Concepts to Remember
- Read the scenario before looking for a memorised answer.
- Find the constraint that changes the correct option.
- Eliminate answers that are true in general but not in this case.
TExam Day Tips
- Watch for words such as best, first, most likely and least administrative effort.
- Review why wrong options are wrong, not only why the correct option is correct.
Key takeaway
Answer the scenario, not the keyword: identify the specific constraint before choosing the most familiar-sounding option.
Real-world example
How this comes up in practice
A network engineer segments a warehouse floor into three subnets: 20 scanners, 5 printers, and 2 management hosts. Picking the wrong mask wastes addresses or leaves too few usable hosts. Exam questions test whether you can apply CIDR notation, calculate block size, and identify the correct usable-host range for a given prefix.
What to study next
Got this wrong? Here's your next step.
Identify which exam domain this question belongs to, review the core concept, then practise similar questions from the same domain.
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Content Security — study guide chapter
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FAQ
Questions learners often ask
What does this 350-701 question test?
Content Security — This question tests Content Security — Read the scenario before looking for a memorised answer..
What is the correct answer to this question?
The correct answer is: HTTPS decryption is disabled globally or for the specific category. — When HTTPS decryption is disabled globally or for a specific category, the WSA cannot generate a certificate to intercept and inspect the traffic. In explicit proxy mode, the WSA must decrypt HTTPS traffic to apply security policies; without decryption enabled, the proxy simply forwards the traffic without generating a certificate, causing the browser to fail to establish a secure connection for sites that require inspection.
What should I do if I get this 350-701 question wrong?
Identify which exam domain this question belongs to, review the core concept, then practise similar questions from the same domain.
Are there clue words in this question I should notice?
Yes — watch for: "most likely". Probability qualifier — the question wants the most probable cause or outcome, not a guaranteed one. Eliminate low-probability options.
What is the key concept behind this question?
Read the scenario before looking for a memorised answer.
About these practice questions
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Last reviewed: Jun 25, 2026
This 350-701 practice question is part of Courseiva's free Cisco 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 350-701 exam.
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