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I have inherited a SBS2003 server, one of the users is attempting to set up his iphone on it. the server has been working fine for the past 5 yrs or so.

it is using a xxxx.dnsalias.com for a static ip, there were no server certificates created so I have created a self signed one. But running through the www.testexchangeconnectivity.com and https://store.accessmylan.com/main/diagnostic-tools tools they both fail on connecting through port 443.

running the accessmylan tester on the internal network it seems fine, just raising queries about the self signed certificate.

the router is a draytek vigor 2820. It has a port redirection set for port 443 to go to server ip on port 443. In IIS default web site is set to require SSL.

I dont know where it is failing!

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Have you exported the self-signed certificate with the private key and imported that to the iphone? Other users can't connect either i suppose?

Since the Iphone doesn't trust the certificate now you need to import that to the phone. Otherwise you must buy a third party certificate that the iphone already trust.

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