Microsoft Passport login - am I signed in or not?

Terence Park 0 Reputation points
2026-03-17T07:43:18.6733333+00:00

I use Windows 10. My PC does not support biometric input.

Engaging with a prospective employer, I discovered that details of my engagement are accessed via a front end that requires a Microsoft Passport login. Having provided the appropriate Microsoft Passport login credentials, a Microsoft popup reports the following: Sorry we're having trouble signing you in. Should they be telling me this if I'm already signed in?

As noted this related to a potential job... I can sidestep the embarrassment of a process that doesn't work because at a high level, it's just a simple thing poorly executed which can be glossed over at interview stage... but I can well imagine how dispiriting it can be, if an important process gets snarled up by a poorly explained additional layer of control. Anyhow I have used used Microsoft products for over 30 years and I think it is not unreasonable to expect simple processes to just work.

Microsoft Security | Microsoft Authenticator

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  1. AI answer

    2026-03-17T07:43:39.5133333+00:00

    The message “Sorry, but we’re having trouble signing you in” means the Microsoft sign-in process is failing, even if credentials were entered correctly. In this state, the account is not considered successfully signed in to that application or site.

    For Microsoft services that use modern authentication (such as Microsoft 365, Azure, or other apps fronted by Microsoft Entra ID), this error typically indicates an authentication problem on the service side rather than a problem with the local Windows sign-in or with the device’s lack of biometrics. The service may be encountering an Entra authentication error state and interrupting the sign-in flow.

    In practice this means:

    • The sign-in did not complete successfully for that web front end.
    • The application should not treat the session as authenticated, even if a Windows session is already active.
    • The issue is usually with how the relying application or its identity configuration is set up (for example, domain or federation configuration, user ID/UPN handling, or other Entra-side issues), not with the end user’s long-standing Microsoft usage or expectations.

    Because this is tied to the prospective employer’s front end, the correct next step is for their IT/admin team to review the sign-in configuration and associated Microsoft Entra error details. The generic “Sorry, but we’re having trouble signing you in” message is the standard surface for these backend authentication issues.

    References:

    AI-generated content may be incorrect. Read our transparency notes for more information.

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