If you’re having an issue connecting your iPhone to your Exchange 2003 server, either standalone or Windows Small Business Server 2003, try resetting your exchange IIS folders. Microsoft has a full guide on resetting the folders from scratch, which when followed, has resolved the majority of iPhone related issues we’ve encountered.
Microsoft Support Site
Also, ensure that you are using a trusted 3rd party SSL cert on your exchange server. Self-signed certificates seem to cause problems later on. To ensure that you have a trusted 3rd party certificate, browse to your mailserver’s OMA directory in Internet Explorer. If you are presented with a login screen, then your SSL is likely grated from a 3rd party. If you have to acknowledge any security warnings, chances are your SSL is self-signed.
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