Quick Answer
The correct configuration is to enable Seamless Single Sign-On (SSO) for the domain. This works because Seamless SSO integrates with Azure AD Application Proxy to silently authenticate users against on-premises Active Directory using Kerberos delegation, allowing them to access published apps without re-entering credentials even after selecting 'Keep me signed in'. On the AZ-500 exam, this scenario tests your understanding of how to eliminate password prompts while preserving security—a common trap is confusing Seamless SSO with password hash sync or federation, but the key distinction is that Seamless SSO leverages the user’s existing domain-joined session. Remember that Seamless SSO is a domain-level feature, not an app-level setting, and it requires the user’s device to be joined to the on-premises AD. Memory tip: think “Seamless = Session reuse” to recall it avoids password prompts by reusing the Kerberos ticket from the domain login.
This AZ-500 practice question tests your understanding of secure identity and access. This is a configuration task: choose the command set that satisfies every stated requirement. Small differences — like 'secret' vs 'password' or 'transport input ssh' vs 'all' — change whether the answer is correct. 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.
Your company has a Microsoft Entra ID tenant and uses Azure AD Application Proxy to publish on-premises web apps. Users report that they are prompted for their password every time they access the app, even though they selected 'Keep me signed in'. You need to improve the sign-in experience without compromising security. What should you configure?
Configure conditional access policies to require device compliance
Why wrong: Does not reduce sign-in prompts.
Enable Seamless Single Sign-On (SSO) for the domain
Allows automatic sign-in for domain-joined devices.
Enable B2B collaboration for the app
Why wrong: For external users.
Set 'Session lifetime' to 'Permanent' in sign-in frequency
Why wrong: Only controls session expiry, not initial SSO.
Answer choices
Answer the question above first, then reveal the full breakdown to understand why each option is right or wrong.
Correct answer & explanation
Enable Seamless Single Sign-On (SSO) for the domain
Seamless Single Sign-On (SSO) for the domain integrates with Azure AD Application Proxy to automatically authenticate users against on-premises Active Directory without prompting for credentials. This eliminates repeated password prompts while maintaining security by leveraging Kerberos delegation and the user's existing domain session.
Key principle: Answer the scenario, not the keyword: identify the specific constraint before choosing the most familiar-sounding option.
Answer analysis
For each option: why learners choose it and why it is or isn't the right answer here.
Configure conditional access policies to require device compliance
Why it's wrong here
Does not reduce sign-in prompts.
Enable Seamless Single Sign-On (SSO) for the domain
Why this is correct
Allows automatic sign-in for domain-joined devices.
Related concept
Read the scenario before looking for a memorised answer.
Enable B2B collaboration for the app
Why it's wrong here
For external users.
Set 'Session lifetime' to 'Permanent' in sign-in frequency
Why it's wrong here
Only controls session expiry, not initial SSO.
Common exam traps
The trap here is that candidates often confuse session lifetime settings (Option D) with SSO functionality, thinking that making a session 'permanent' will stop password prompts, when in fact it only extends the token lifetime without addressing the underlying lack of automatic authentication.
Detailed technical explanation
Seamless SSO works by having Azure AD respond to authentication requests with a 401 challenge that includes a specific domain hint; the user's browser then sends a Kerberos ticket to a local domain controller, which is validated and converted into a SAML assertion by Azure AD. This process requires the client machine to be domain-joined or hybrid-joined and the Azure AD Connect Seamless SSO feature to be enabled, with the AZUREADSSOACC computer account created in the on-premises AD.
Key takeaway
Answer the scenario, not the keyword: identify the specific constraint before choosing the most familiar-sounding option.
Real-world example
A company's IT admin needs to give a contractor read-only access to production logs without sharing account credentials. Using role-based access control (RBAC) and temporary scoped permissions — not a permanent shared password — is the correct pattern. Questions like this test whether you can apply least-privilege access across cloud identity services.
What to study next
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Secure identity and access — study guide chapter
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FAQ
Secure identity and access — This question tests Secure identity and access — Read the scenario before looking for a memorised answer..
The correct answer is: Enable Seamless Single Sign-On (SSO) for the domain — Seamless Single Sign-On (SSO) for the domain integrates with Azure AD Application Proxy to automatically authenticate users against on-premises Active Directory without prompting for credentials. This eliminates repeated password prompts while maintaining security by leveraging Kerberos delegation and the user's existing domain session.
Identify which exam domain this question belongs to, review the core concept, then practise similar questions from the same domain.
Read the scenario before looking for a memorised answer.
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Last reviewed: Jun 25, 2026
This AZ-500 practice question is part of Courseiva's free Microsoft 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 AZ-500 exam.
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