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SBS 2003 - Outlook Anywhere/HTTPS (Outlook 2010) renew certificate problems

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Last Modified: 2016-04-04
Hi Experts,

The self-signed certificate created using the CEICW tool on our SBS 2003 expired on the weekend.  I tried running the CEICW tool with the following options:
1. Do not change connection type
2. Allow following web site services from internet (OWA, Outlook Mobile Access, Outlook via the Internet).
3. Create a new Web server certificate - domain name xxxxxx.yyyyyyyy.zzz
4. Do not change Internet e-mail configuration

The process succeeded.  However, on the client machine, I installed the new certificate in the Trusted Root Certification Authorities as I have done in the past and Outlook 2010 keeps giving me Error 8 (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 connect to the proxy server xxxxxx.yyyyyyyy.zzz).  Even after installing the certificate, Internet Explorer keeps stating there is a problem with the certificate.

I am going to bring one of my old remote machines into the office later today to compare the old certificate on the client machine with the new certificate to see if any of those things could be my issue.

I look forward to any help you can provide and thanks in advance.
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