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Self Signed certificate for Exchange 2003 and ActiveSync

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Last Modified: 2015-12-24
I have a Windows 2003 SBS server (very out of date and unsupported I know) and currently have a RapidSSL certificate installed which allows me to configure Exchange email on my iPhone.
Instead of buying a certificate each year I would like to generate a self signed one (there's only me and one other person using the Exchange mail). I've run through the "connect to the Internet" wizard and it's generated and installed a certificate but when I run the Microsoft Connectivity Analyzer it rejects it with an error "The certificate chain didn't end in a trusted root...."
Is what I'm trying to do possible and if so where am I going wrong?
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