Self Signed certificate for Exchange 2003 and ActiveSync

ClintonK used Ask the Experts™
I have a Windows 2003 SBS server (very out of date and unsupported I know) and currently have a RapidSSL certificate installed which allows me to configure Exchange email on my iPhone.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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A self signed SSL will always generate errors because it isn't a proper, publicly provided certificate and is meant to be internal only.
The error you're getting is correct and to be expected unless you purchase a proper SSL again.
While the Analyzer might give you errors, if you installed the self signed certificate properly,
your iPhone will have no problem using it. When setting up the ActiveSync account (or Exchange account, even on Android), it will ask you only ONCE to trust this certificate or not. If you choose to trust it, it will never ask you this again, and the account WILL function properly.


All working thanks. I've ignored the errors from the analyser and installed a self-signed certificate. I can now connect the iphone successfully.

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