Internally, I have no problems getting to https://internal.mail.company.com, but externally https://mail.company.com does not work. However, http://mail.company.com says that you need https:// to connect to the site. Port 443 is enabled and allowed on my firewall. When I remove the certificate from the site and uncheck the SSL from the phone, the users' mail synchronizes again.
I'm pulling my hair out. Obviously, something is wrong. What do I do?
A well documented issue with the Pocket PC 2002 operating systems is that, if you are going to establish an HTTPS connection, the device must explicitly trust the Root certificate authority (CA). If you are running a Windows CA, and not using a third-party like VeriSign, then the Pocket PC will not trust your root CA without some additional work. See Sample to add root certificates to Pocket PC 2002.
According to Microsoft, this is not an issue with Pocket PC 2003. I don't think this is your problem though, because you are working internally without any errors.
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