SBS Server and Office 365

Just took on a client who uses SBS Server 2008. Their prior IT admin moved their email from on premises to Office 365. When the users now open Outlook they get a Security Alert: Information you exchange...The security certificate was issued by a company you have not chosen to trust. View the certificate to determine whether you want to trust the certifying authority.

When the click yes to proceed, Outlook functions properly and they receive/send email without issue all day.

How do I resolve this? It appears that Outlook is finding an internal certificate.
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No MoreCommented:
Have a look on your internal CA to see what certs are issued
No MoreCommented:
If it have been moved to cloud you must re-create outlook profile to and let it connect to office 365


View certificate and download / install and add it to trusted certificates
YortAuthor Commented:
@David_FIala - I did do that. As a matter fact, the Office 365 domain name it's a completely different than what used internally. But somehow this certificate issue keeps coming up.
No MoreCommented:
Does user have UPN prefix of new domain ?

go to control panel - Mail and check how many profiles you have there and what's the default one

I wonder if the old DNS records on Hosting still include pointer to Exchange server
YortAuthor Commented:
That was the issue. I removed the offending certificate via IIS 7 and the problem is no more! Thanks!
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