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Synchronizing Pocket PCs with Exchange 2003 mailboxes

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QUESTION POSED ON: 24 August 2005
A group of my users recently picked up new cell phones that are Pocket PCs. I was able to set up ActiveSync with my Exchange 2003 box so that users can synchronize their mailboxes to their phones. I wanted to make them use Secure Sockets Layer. I set up a certificate and applied it to my default Exchange site.

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?


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You only mention one Exchange server, yet there are two URLs. Is there also a front-end server that the clients have to go through from the Internet? If so, then the certificate must be applied to the front-end server, not the server with mailboxes on it.

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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Related information from SearchExchange.com:

  • Reference Center: Mobile and wireless resources
  • Reference Center: User authentication tips and resources

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