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O365 continuously prompt for credentials after I turn on my web filtering

Mahmood Maleki

Hello there,

My users are continuously facing O365 credentials prompt after I turn on web filtering on my UTM 9. Does anybody has any idea how to fix this issue?

thanks in advance,

Mahmood



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  • 0

    simple answer: set the exceptions correctly

    alternative answer: don't use webfiltering as microsoft says for example for the skype4business part of O365.

    Microsoft has a horrible long list of networks, URLs and IPs to except, it is really no fun at all.

    Gruß / Regards,

    Kevin
    Sophos CE/CA (XG+UTM), Gold Partner

  • 0

    This is one that crops up often for me (though it's AD credentials they get prompted for).

    As mentioned you need exceptions in for O365 traffic to start with - assuming you are on about the full Outlook client you need the three usual O365 exceptions (outlook.com, office365.com and autodiscover-s.outlook.com).

    In addition Outlook will trash around a series of autodiscover URL's which are dependent on your domain, I've found it easiest to search your filter log for "autodiscover" and add them to the exception list, there will probably be around three or four more URL's, or if you have regex skills you can simplify that down.

    Except them from authentication and that should sort it.

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