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350-701 A hospital uses Cisco ESA for email security Practice Question
A hospital uses Cisco ESA for email security. The compliance team requires that all emails containing protected health information (PHI) be encrypted before leaving the organization. The administrator has configured a content filter that matches emails containing patterns like 'Patient ID: [0-9]{9}' and sends them to the encryption service. However, some encrypted emails are being rejected by the recipient's mail server because the encryption is applied after the email has already been processed. What is the most likely reason for this issue?
⚠ Common exam trap
Cisco often tests the distinction between 'deliver then encrypt' and 'encrypt then deliver' as a common misconfiguration, where candidates assume encryption is always applied before delivery without checking the order of actions in the content filter or mail policy.
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 encryption action is configured as 'deliver then encrypt' instead of 'encrypt then deliver'.
Cisco ESA processes emails through a series of mail policies and content filters before delivery. If the encryption action is configured as 'deliver then encrypt', the email is first sent to the recipient's mail server, and then encryption is attempted as a separate, asynchronous action. This means the email leaves the organization unencrypted, and the recipient's server may reject it if it expects encryption from the start. The correct configuration should be 'encrypt then deliver', which ensures the email is encrypted before it is queued for delivery, preventing rejection due to unencrypted content.
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 encryption action is configured as 'deliver then encrypt' instead of 'encrypt then deliver'.
Why this is correct
Order of actions matters.
- ✗
The content filter is only applied to incoming emails, not outgoing.
Why it's wrong here
Outgoing emails are filtered as well.
- ✗
The recipient's mail server does not support the encryption protocol used.
Why it's wrong here
Encryption is transparent.
- ✗
The email exceeds the maximum size limit for encryption.
Why it's wrong here
Size limit not mentioned.
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JA
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.