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You can try installing the certificate by itself. &nbsp;Just open the file, and select &quot;Install...&quot;, then instead of automatically selecting the location, Browse the stores, check the box for &quot;Show Physical Stores&quot;, and under Trusted Root Certificate Authorities, put the cert in Local Computer. &nbsp;Then try browsing the site through OWA, and see if you get a certificate error. &nbsp;<br />
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Is this a SAN cert?
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You can try installing the certificate by itself.  Just open the file, and select "Install...", then instead of automatically selecting the location, Browse the stores, check the box for "Show Physical Stores", and under Trusted Root Certificate Authorities, put the cert in Local Computer.  Then try browsing the site through OWA, and see if you get a certificate error.  

Is this a SAN cert?

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I've been asked by my customer to resolve an issue with being asked for a certificate every time they log on to their Outlook. &nbsp;It mentions the certificate twice. &nbsp;I have taken the certificate from the Public Downloads directory on the server and attempted install with the InstallCertificate file. &nbsp;I get The certificate was not installed message. &nbsp;<br />
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Any ideas of what I can do to rid this system of this error. &nbsp;It happens each time they open their Outlook. &nbsp;If they click yes twice, it connects. &nbsp;I'd like the message to go away all together.
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I've been asked by my customer to resolve an issue with being asked for a certificate every time they log on to their Outlook.  It mentions the certificate twice.  I have taken the certificate from the Public Downloads directory on the server and attempted install with the InstallCertificate file.  I get The certificate was not installed message.  

Any ideas of what I can do to rid this system of this error.  It happens each time they open their Outlook.  If they click yes twice, it connects.  I'd like the message to go away all together.

The certificate was not installed.  Please try again.  Outlook 2010, Exchange 2007, Windows XP Pro SP3 client

Windows Server 2008 and Windows Server 2008 R2, based on the Microsoft Vista codebase, is the last 32-bit server operating system released by Microsoft. It has a number of versions, including including Foundation, Standard, Enterprise, Datacenter, Web, HPC Server, Itanium and Storage; new features included server core installation and Hyper-V.

Windows Server 2008

Exchange is the server side of a collaborative application product that is part of the Microsoft Server infrastructure. Exchange's major features include email, calendaring, contacts and tasks, support for mobile and web-based access to information, and support for data storage.