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Moved from local Exchange 2007 to Exchange Online (O365) Old local SSL cert still pops up in Outlook.

Posted on 2014-02-14
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Last Modified: 2014-02-15
We have recently moved to O365 for email. Our on premises Exchange 2007 box is still up and running for some internal email processing (a copier, and some industrial machinery that is behind the times).

All of the Outlook installs have a new profile configured for O365. Now and again, an SSL warning pops up in Outlook for the local Exchange server. How can I make Outlook forget this exists?

Thanks!

Tom
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Question by:Tom_Bombaci
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Expert Comment

by:David Johnson, CD, MVP
ID: 39860103
you've updated your mx and autodiscover records?
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Author Comment

by:Tom_Bombaci
ID: 39860708
Yes. I have changed the autodiscover cname in my local DNS to point to the outlook.com servers as well as the MX record.

Actually, the local domain name is xxxx.local and I have an added DNS entry for xxxx.com I only added the autodiscover to the xxxx.com DNS entry. Do I need to add it to the xxxx.local as well?
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Accepted Solution

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Simon Butler (Sembee) earned 2000 total points
ID: 39861596
The clients are still querying the domain for Autodiscover information. That is because you still have the Exchange 2007 server in place. While that is in place you cannot stop them from doing that. Autodiscover DNS records aren't going to help because they don't use them.

Two things to do here.
1. Remove the Exchange 2007 server and replace it with an IIS SMTP server to do the email processing. That will save you from having to patch the Exchange 2007 server to maintain it.

2. Change the Autodiscover value you can see here:
get-clientaccessserver | select identity, autodiscoverserviceinternaluri to point to the host name you have been told to use for Autodiscover for Office365. That way if a client does query the domain they are then pointed to the Office365 installation instead.

Simon.
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Author Closing Comment

by:Tom_Bombaci
ID: 39861744
Thank you. That explains why I couldn't configure Outlook locally without using config365.com

Thank you again!

Tom
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