iPhones are supposed to be easy, right?  Well, they are extremely easy to set up, as long as your Exchange environment is ready for ActiveSync.  If these are the first devices you’ll be using as ActiveSync clients, you may have some work to do, primarily if you are using a single-server Exchange environment.

At first, I had lots of trouble, with not a lot of ideas on where to start troubleshooting.  You try with the basics like HTTP logs, firewall logs, and the Windows event log.  Well it’s not always easy to tell when you’re on the right track.

In any case, when you run your Outlook Web Access system on the same server as your mailbox stores, you generally are going to have a lot of set-up to do for Outlook Mobile Access, ActiveSync, or RPC over HTTP.

On to the fix.  After trying several things, I stumbled upon a word doc on Microsoft’s site, highlighting the steps to take when you’d like OMA and ActiveSync to work on a single-server Exchange installation.  The Page numbered Thirteen is where the tasty bits start.

Essentially, services like OMA and ActiveSync are built on top of Outlook Web Access, only they are unable to communicate with the OWA services via HTTPS.  The steps in the document lead you to a way to create an instance of OWA on your server which will be accessed by only by OMA and ActiveSync.  After going through the steps in the document, the shiny iPhones worked like champs, and the IT staff at my company can begin evaluating their fitness as Blackberry killers.  The prospects are good for full on Blackberry annihilation, except there has been reluctance about the on-screen keyboard.