The answer is certificate pinning, specifically HTTP Public Key Pinning (HPKP), which causes the certificate error on the banking site. When Cisco WSA performs HTTPS decryption, it generates a new certificate on the fly signed by the company’s custom CA, but banking websites often embed a hash of their original public key or certificate into the browser’s security policy. If the WSA’s generated certificate does not match that pinned public key, the browser rejects the connection as untrusted, even though the CA is valid. On the Cisco SCOR 350-701 exam, this scenario tests your understanding of how HTTPS decryption interacts with modern security mechanisms like certificate pinning—a common trap is assuming the custom CA trust alone resolves all errors. Remember the mnemonic: “Pinning pins the public key, not the CA.”
350-701 Content Security Practice Question
This 350-701 practice question tests your understanding of content security. Read the scenario carefully and evaluate each option against the stated constraints before committing to an answer. 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 using Cisco Web Security Appliance (WSA) in explicit proxy mode has enabled HTTPS decryption with a custom CA certificate. A user reports that a specific banking website displays a certificate error message. The administrator verifies that the WSA is generating a certificate for that site. What is the most likely cause of the error?
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 the question above first, then reveal the full breakdown to understand why each option is right or wrong.
Correct answer & explanation
✓
The banking website uses HTTP Public Key Pinning (HPKP) or Certificate Pinning.
Banking websites often use dynamic certificates with extended validation (EV) and may implement certificate pinning. However, the WSA's generated certificate will not match the original certificate's public key or subject alternative names if the site uses pinning. Option B is correct because certificate pinning will cause a mismatch. Option A is incorrect because the CA certificate is already trusted. Option C is incorrect because the WSA's certificate is generated on the fly. Option D is possible but less specific to banking sites.
Key principle: NAT direction and interface roles matter as much as the IP address mapping. Inside/outside designation controls which traffic is translated.
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 banking website uses HTTP Public Key Pinning (HPKP) or Certificate Pinning.
Why this is correct
Pinned certificates are compared to the original, and the WSA's generated certificate does not match, causing an error.
Clue confirmation
The clue word "most likely" in the question point toward this answer.
Related concept
Static NAT maps one inside address to one outside address.
✗
The WSA's time is not synchronized with the NTP server, causing certificate validity issues.
Why it's wrong here
Time sync issues would affect all HTTPS sites, not just this bank.
✗
The WSA is not configured to generate certificates for that domain.
Why it's wrong here
The administrator verified a certificate is generated.
✗
The user's browser does not trust the WSA's CA certificate.
Why it's wrong here
If the CA is trusted, no error would occur; the error is specific to the certificate presented.
Common exam traps
Common exam trap: NAT rules depend on direction and matching traffic
NAT is not only about the public address. The inside/outside interface roles and the ACL or rule that matches traffic are just as important.
Detailed technical explanation
How to think about this question
NAT questions usually test address translation, overload/PAT behaviour, static mappings and whether the right traffic is being translated. Read the interface direction and address terms carefully.
KKey Concepts to Remember
Static NAT maps one inside address to one outside address.
PAT allows many inside hosts to share one public address using ports.
Inside local and inside global describe the private and translated addresses.
NAT ACLs identify traffic for translation, not always security filtering.
TExam Day Tips
→Identify inside and outside interfaces first.
→Check whether the scenario needs static NAT, dynamic NAT or PAT.
→Do not confuse NAT matching ACLs with normal packet-filtering intent.
Key takeaway
NAT direction and interface roles matter as much as the IP address mapping. Inside/outside designation controls which traffic is translated.
Real-world example
How this comes up in practice
A small business has 20 workstations on the 192.168.1.0/24 network and one public IP from its ISP. The router uses PAT (NAT overload) so all 20 devices share one public address using different source ports. NAT questions test whether you understand the four address terms and which direction each translation applies.
What to study next
Got this wrong? Here's your next step.
Review the four NAT address types (inside local, inside global, outside local, outside global), PAT port overload, and static vs dynamic NAT use cases. Then practise related 350-701 NAT questions on configuration and troubleshooting.
Content Security — This question tests Content Security — Static NAT maps one inside address to one outside address..
What is the correct answer to this question?
The correct answer is: The banking website uses HTTP Public Key Pinning (HPKP) or Certificate Pinning. — Banking websites often use dynamic certificates with extended validation (EV) and may implement certificate pinning. However, the WSA's generated certificate will not match the original certificate's public key or subject alternative names if the site uses pinning. Option B is correct because certificate pinning will cause a mismatch. Option A is incorrect because the CA certificate is already trusted. Option C is incorrect because the WSA's certificate is generated on the fly. Option D is possible but less specific to banking sites.
What should I do if I get this 350-701 question wrong?
Review the four NAT address types (inside local, inside global, outside local, outside global), PAT port overload, and static vs dynamic NAT use cases. Then practise related 350-701 NAT questions on configuration and troubleshooting.
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?
Static NAT maps one inside address to one outside address.
About these practice questions
Courseiva creates original exam-style practice questions with explanations and wrong-answer analysis. It does not publish real exam questions, exam dumps, or protected exam content. Learn why practice questions differ from exam dumps →
These questions test the same concept from different angles. Work through them to make sure you can recognise it however the exam phrases it.
Variation 1. 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?
easy
✓ A.HTTPS decryption is disabled globally or for the specific category.
B.The website uses certificate pinning, which prevents interception.
C.The WSA CA certificate is not installed in the user's browser trust store.
D.The WSA is configured to bypass decryption for the user's subnet.
Why A: 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.
Variation 2. A Cisco WSA appliance is configured with explicit proxy mode. Users report that they cannot access external HTTPS websites, but HTTP works fine. The proxy logs show 'SSL handshake failed' errors. What is the most likely reason?
hard
A.The HTTPS proxy port is not configured on the WSA.
✓ B.The WSA's SSL certificate is not trusted by the clients.
C.The WSA is configured to forward HTTPS traffic without decryption.
D.Client certificates are required for authentication.
Why B: In explicit proxy mode, the Cisco WSA must intercept HTTPS traffic by performing a man-in-the-middle (MITM) decryption. For this to work, the WSA presents its own SSL certificate to the client. If that certificate is not trusted by the client's browser or operating system (i.e., not installed in the trusted root certificate store), the client will reject the SSL handshake, resulting in 'SSL handshake failed' errors. HTTP traffic is unaffected because it does not involve certificate validation.
Last reviewed: Jun 24, 2026
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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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