Hi,
For the conditional access not applied issue, based on my research, it seems the conditional access will be applied when the user tries to authenticate to Azure AD from app.
https://learn.microsoft.com/en-us/mem/intune/protect/app-based-conditional-access-intune
For our situation, as the user is already login into outlook. the token is cached on device side. So the authentication does not happen which cause the conditional access not applied. But when we remove the account and add again, it trigger the authentication and the conditional access is applied.
After researching, i find a setting named Sign-in frequency defines the time period before a user is asked to sign in again when attempting to access a resource.
https://learn.microsoft.com/en-us/azure/active-directory/conditional-access/howto-conditional-access-session-lifetime
Maybe we can set this setting to fix our issue. As Conditional Access is a feature in Azure AD, Azure AD support may be more familiar with it, we suggest to contact them to double confirm our issue and guide for the sign-in option. Here is the forum for Azure AD support:
https://learn.microsoft.com/en-us/answers/topics/azure-active-directory.html
Thanks for the understanding. have a nice day!
Best regards.
Crystal