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350-701 Practice Question: A Cisco WSA appliance is configured with explicit…
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?
⚠ Common exam trap
Cisco often tests the distinction between proxy configuration (port settings) and SSL decryption trust (certificate validation), leading candidates to mistakenly focus on port numbers or forwarding modes instead of the certificate trust chain.
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 WSA's SSL certificate is not trusted by the clients.
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.
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 HTTPS proxy port is not configured on the WSA.
Why it's wrong here
HTTPS proxy port 3128 is default; if not configured, HTTP may not work either.
- ✓
The WSA's SSL certificate is not trusted by the clients.
Why this is correct
Clients must trust the WSA's certificate for HTTPS interception.
- ✗
The WSA is configured to forward HTTPS traffic without decryption.
Why it's wrong here
Without decryption, HTTPS should still work as a tunnel, but errors suggest interception issues.
- ✗
Client certificates are required for authentication.
Why it's wrong here
Client certificates are used for user authentication, not for HTTPS connectivity.
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Written by Johnson Ajibi, MSc IT Security
Senior Network & Security Engineer · founder of Courseiva
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.