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I have a client that has Windows SBS 2003. They currently have remote mail enabled, ie: prompts to accept to use the certificate, then allows them to use remote mail in the internet browser.

I am trying to setup Outlook on a remote computer to use RPC over HTTP. Is there a way to get the certificate installed on their computer so that it will work.

At the moment, I have put all the correct settings in the local mail profile, but when I try and open Outlook it is coming up with:

There is a problem with the proxy server's security certificate. The security certificate is not from a trusted certifying authority. Outlook is unable to connec to the proxy server (Error code 8).

Please help. I have heard that there is a way to have the certificate installed via going to a website on the SBS server that will install the certificate to make this work?


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up vote 1 down vote accepted
  1. Open up IE.
  2. Navigate to
  3. Up next to the address bar, click where it says "Certificate Error" and go down to "View Certificate"
  4. Install certificate and choose to put it in the "Trusted root certification authorities" store

Oh...and buy a signed cert...they're only ~$30/'s not worth this hassle.

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But I've heard that there's a way to get SBS through IIS to automatically install the certificate? – The Woo Feb 21 '11 at 2:15
IIS cannot automatically install a certificate. If it could, that would defeat the purpose of certificate signing. There is a way to distribute the certificate through group policy though. Is the machine your on part of the domain? – Jason Berg Feb 21 '11 at 3:06

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