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

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?
ErgsAsked:
Who is Participating?
I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

hecgomrecCommented:
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.)
0
ErgsAuthor Commented:
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??
0
hecgomrecCommented:
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?
0
ErgsAuthor Commented:
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.
0

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
ErgsAuthor Commented:
It is what worked
0
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today
Email Servers

From novice to tech pro — start learning today.

Question has a verified solution.

Are you are experiencing a similar issue? Get a personalized answer when you ask a related question.

Have a better answer? Share it in a comment.