Troubleshooting having to log in multiple times using Microsoft 365

If you are being prompted to log in again every time you start a new session, check the following. You should only have to log in infrequently, but this depends on your corporate policies.

Browser Configuration and Cookies

1. Cookies Disabled or Blocked:

   • If the browser settings block cookies or are set to clear cookies upon closing, the session information cannot be retained, leading to reauthentication prompts.

2. Third-Party Cookies Blocked:

   • Azure AD / Entra might require third-party cookies to maintain the session. If the browser blocks third-party cookies, this could interrupt the session continuity.

3. Browser Privacy Settings:

   • High privacy settings can block session cookies. Users should check their privacy settings to ensure they allow cookies from the relevant domains.

4. Incognito/Private Browsing Mode:

   • Sessions and cookies are not saved in incognito or private browsing modes. Ensure users are not using these modes when logging into SmartAssist.

5. Browser Extensions:

   • Some extensions, particularly privacy-focused ones, can block cookies and interfere with session management. Users can try disabling extensions to see if it resolves the issue.

Corporate Policies

1. Conditional Access Policies:

   • Organizations may have conditional access policies in place that enforce frequent reauthentication for security reasons. Check with the IT department to see if such policies are enforced for specific users or groups.

2. Device Compliance Policies:

   • If the organization enforces compliance policies requiring devices to meet certain security standards, non-compliant devices might trigger reauthentication.

3. Session Timeout Settings:

   • Azure AD / Entra allows organizations to set session timeout policies. Ensure that these settings are not configured to expire sessions too frequently.

4. Single Sign-On (SSO) Configuration:

   • Issues with the SSO configuration might cause session problems. Ensure that the SSO settings are correctly configured to support persistent sessions.

5. Multi-Factor Authentication (MFA) Requirements:

   • If MFA is required for every session, users will need to reauthenticate each time they start a new session.

Troubleshooting Steps

1. Check Browser Settings:

   • Ensure cookies are enabled and not set to be cleared upon closing the browser.
   • Allow third-party cookies, at least for the domains used by Azure AD / Entra.

2. Review Corporate Policies:

   • Work with the IT department to review conditional access, session timeout, and device compliance policies.
   • Ensure these policies are not too restrictive and align with the desired user experience.

3. Test with Different Browsers/Devices:

   • Have affected users try different browsers or devices to determine if the issue is isolated to specific configurations.

4. Review Azure AD / Entra Settings:

   • Check the settings in the Azure AD / Entra portal to ensure they support persistent sessions and are not enforcing overly frequent reauthentication.