I’m having difficulty getting an iPhone to connect to Microsoft Exchange 2007 when using certificates. Here is what I have done so far. I have Exchange set so that certificates are not required and it’s doing basic authentication. With this configuration I can connect my iPhone 3GS just fine and get email, calendar etc. I then used the iPhone configuration utility to create a profile. This profile includes a self-generated certificate that will authorize a device to communicate with our Exchange server. This certificate is the same one we use to allow users to use Remote Web Workplace (RWW) and Outlook for Web Access (OWA). I loaded the certificate using the "Credentials" payload. I could not load the certificate using the "Exchange Activesync" payload because the certificates were not listed when I tried. I have loaded this profile onto my iPhone. I can verify that the profile and the certificate were loaded successfully. I then changed Exchange to require a certificate and I cannot connect. The message I get is “Cannot Get Mail. The connection to the server failed”. If I turn off the option to require a certificate in Exchange 2007 I can get my mail just fine. Because I can verify that the certificate was loaded onto the phone, I believe the problem may lie with Exchange but I’m stuck as where to look. Our server is running Windows SBS 2008 x64. This includes Exchange 2007. The server is up to date with all patches and service packs. Thanks in advance for any help you can provide.

Use trusted 3rd party certificates instead. Using self-signed certificates is not recommended for mobile devices or remote users.