Exchange - The security certificate has expired or is not yet valid

Posted on 2014-08-03
Last Modified: 2014-08-10
Hi Guys

I have a client who is using Microsoft Office 365 Exchange, 2 of the users Outlook keeps asking for a password and will not connect to exchange.

From either machine we can logon using a browser but Outlook will not connect, keeps asking for password. When I first start Outlook I get a Security Alert... "The security certificate has expired or is not yet valid"

When I view the certificate, it has Valid from 24/03/2012 to 24/03/2014 and issues by the local server in the office. Yes we run SBS2011, they use to have exchange locally but migrated to Office 365 a couple years ag0 - having said that the exchange services were still running on the local server which I have since stopped and disabled.

Another thing to note is that the 2 machines having the problem are new machine which were added to the local domain a few weeks ago, there are 3 other machines in the office connecting to Office 365 without any problems?

Any ideas?
Question by:Ergs
    LVL 11

    Expert Comment

    Yes!... the other machines most likely where update/upgraded to the 365 so their credentials.

    Besides, the certificate being really expired the fact that outlook keeps asking for password could lead to few things, so let rule 5 for now;  Make sure the Network card on the new machines is set to be always on by turning of the power Management features. Also, make sure the right credentials are entered and the user can choose to save these.

    One of the most common reason why outlook ask for credentials is a lost of communication to the server, in this case, this could be cause by wrong driver for the network card, cable problems or a bad network appliance (switch, router, etc.)

    Author Comment

    I don't think there is anything wrong with the network card, I was logged on remotely while doing my testing and I was on the machine for hours without a drop out.

    I'm pretty sure it has something to do with the fact that we are running SBS2008 and Exchange & IIS services were running on the server - I suspect for some reason these 2 clients may be looking at the local SBS server for exchange services??
    LVL 11

    Expert Comment

    Try to check the settings in one of the computers that is connecting to exchange and compare it against the ones not connecting and see if the server's name are the same or not.

    If they are both the same, then they are locating the server properly, if not just changed it to the good one and try.

    Have to try to create any of the accounts that is working elsewhere on any of these machines? or vice versa?

    Accepted Solution

    I went onsite yesterday and did a variety of tests and eventually discovered the problem to be Office 2010. I installed Office 2013 and everything worked fine.

    Author Closing Comment

    It is what worked

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