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One computer will not accept my Cert for OWA

Posted on 2010-01-08
Medium Priority
Last Modified: 2012-05-08
I am trying to use Outlook RPC over HTTP and I can't get it to connect. If I go to my remote.domain.com i get the secuirty alert and I try to install it but the security box keeps coming back every time I visit the website.
I am trying to setup OUTOOK but it is saying: the action could not be completed. the connection to microsoft exchange is unavailable
But I am able to login to the website just have to click yes on the security alert. I have already setup 2 other computers that connect to this domain for email. One is XP Sp 3 with Outlook 2003 the other is Win 7 with Outlook 07. and no problems.
This computer I am trying to connect is XP SP3 w/Outlook 03
Question by:calitech

Expert Comment

ID: 26220552
I had that same problem and sorry to say, Outlook WOULD NOT connect until I fixed the cert. In my case the cert was expired. Telling the browser to 'do it anyway' work only for the browser and has nothing to do with Outlook.

If the reason for the security alert is that that the URL doesn't match, you may be able to fake it out using the host file. If it is simply expired, I can only say that I was unable to get around it until I fixed the cert.

Author Comment

ID: 26220759
Yes I added the line in the host file, but yes the cert might have expired. Any quick ideas on how to issue a new one on SBS 2008?

Author Comment

ID: 26220874
nope cert hasn't expired
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LVL 26

Expert Comment

ID: 26221154
Check the time on the client machine. If it's set to far in the future (like the right month and day but a year or two ahead...it'll throw that error because the according to the computer the cert will look like its expired.
LVL 76

Accepted Solution

Alan Hardisty earned 1000 total points
ID: 26224262
Please review the following link about self-signed certificate limitations, which advises you that for Outlook Anywhere to work, you need to buy a 3rd party ssl certificate:


Godaddy offer very good prices on ssl certs www.godaddy.com

You will need to order a SAN / UCC certificate and there is a good article about which names to include in the certificate here:


Author Closing Comment

ID: 31674849

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