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?
Trap 1: Configure conditional access policies to require device compliance
Conditional Access policies that require device compliance are authorization rules evaluated after authentication, not an authentication mechanism. A compliant device check may block or allow access, but the user still has to provide credentials interactively on first sign-in because CA does not create a security token or cache credentials behind the scenes. In fact, requiring device compliance can add extra MFA or reauthentication requirements, so it does nothing to eliminate or reduce the sign-in prompts you are trying to avoid.
Trap 2: Enable B2B collaboration for the app
B2B collaboration is designed to invite external guest users from other organizations into your tenant so they can access specific apps, and it has no bearing on the authentication experience of your own employees. Enabling B2B for an internal app does not change how domain-joined users are authenticated or whether they see credential prompts. It also introduces external-collaboration settings and user management overhead that are irrelevant to reducing sign-in frequency for your internal workforce.
Trap 3: Set 'Session lifetime' to 'Permanent' in sign-in frequency
The 'Session lifetime' to 'Permanent' option in sign-in frequency only extends how long an already-established session remains valid before the user is asked to reauthenticate, and it does not affect the initial interactive logon. Even with a permanent session, a user who has not yet signed in will still be prompted for username and password once. Additionally, making sessions permanent can weaken security because stolen tokens or devices retain access much longer, which is particularly undesirable if the goal is to reduce prompts without sacrificing control.
- A
Configure conditional access policies to require device compliance
Why it fails: Conditional Access policies that require device compliance are authorization rules evaluated after authentication, not an authentication mechanism. A compliant device check may block or allow access, but the user still has to provide credentials interactively on first sign-in because CA does not create a security token or cache credentials behind the scenes. In fact, requiring device compliance can add extra MFA or reauthentication requirements, so it does nothing to eliminate or reduce the sign-in prompts you are trying to avoid.
- B
Enable Seamless Single Sign-On (SSO) for the domain
Enable Seamless Single Sign-On (SSO) for the domain. This feature, available with Password Hash Synchronization or Pass-through Authentication, silently signs in users on domain-joined, corporate-network-connected devices by reusing their existing Kerberos ticket for AD. When the user tries to reach an Microsoft Entra ID-backed app, Microsoft Entra ID validates the Kerberos ticket and issues a token without showing a password prompt, eliminating most initial sign-in challenges. It requires no additional hardware and is the right setting to address recurring sign-in prompts in this scenario.
- C
Enable B2B collaboration for the app
Why it fails: B2B collaboration is designed to invite external guest users from other organizations into your tenant so they can access specific apps, and it has no bearing on the authentication experience of your own employees. Enabling B2B for an internal app does not change how domain-joined users are authenticated or whether they see credential prompts. It also introduces external-collaboration settings and user management overhead that are irrelevant to reducing sign-in frequency for your internal workforce.
- D
Set 'Session lifetime' to 'Permanent' in sign-in frequency
Why it fails: The 'Session lifetime' to 'Permanent' option in sign-in frequency only extends how long an already-established session remains valid before the user is asked to reauthenticate, and it does not affect the initial interactive logon. Even with a permanent session, a user who has not yet signed in will still be prompted for username and password once. Additionally, making sessions permanent can weaken security because stolen tokens or devices retain access much longer, which is particularly undesirable if the goal is to reduce prompts without sacrificing control.