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SSL stops internal OWA

Posted on 2014-03-30
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Last Modified: 2016-06-03
I am about to migrate SBS 2003 mailboxes to Office 365 / Exchange On-Line but having problems with SSL certificate.
I purchased a Godaddy certificate but as soon as I install it I cannot access Outlook Web Access from the SBS 2003 box.
It makes no difference if I try the ip address/exchange https://remote.domainname.com/exchange or servername/exchange.
I can access OWA externally with no error. but when I view the certificate internally there says there is an error but externally the certificate is ok. - see attached screenshots.
I have recreated the certificate several times but nothing helps.
I can still see the companyweb internally.
Help please. I was meant to have the email migrated this weekend but I have been unable to do so as the security certificate is preventing the Exchange analyser from working.
GA-Certificate-error.jpg
GA-Certificate.jpg
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Question by:gogsck
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Expert Comment

by:Andy M
ID: 39965142
I remember seeing another post about the error shown on the certificate. Don't know if it may help:

http://www.experts-exchange.com/OS/Microsoft_Operating_Systems/Server/2003_Server/Q_23193351.html
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Author Comment

by:gogsck
ID: 39965194
Unfortunately that didn't help.
I created a certificate request. Posted the text into Godaddy's site then when it was processed I downloaded it on the SBS box. I extracted it and installed the certificate using the connect to the internet wizard. I have also tried installing it manually using instructions from Godaddy, a 2 part install usink the .crt file and the .p7b file.
I saw somewhere else to try adding a forward lookup zone to the DNS but it was already in the DNS.
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Accepted Solution

by:
gogsck earned 0 total points
ID: 39965492
fixed it with the help from Godaddy.
I needed to create a SHA-1 certificate and install the intermediate certificate (.p7b) first.
All carried out as per Godaddy instructions and not using connect to the internet wizard
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