Configuring an iPhone to work with Exchange Server 2003

10 pts.
Tags:
ActiveSync
Exchange 2003 configuration
Exchange Server ActiveSync
Exchange synchronization
iPhone
Microsoft Exchange 2003
Server Connection Failed
Hi I've been battling with this for a client for a couple of weeks now. The configuration is slightly unusual as the ES is sitting behind a NATed firewall but I'm using the virtual server and open ports features on the router to pass through the necessary traffic. As a test, I've attempted to see whether OWA will work on the iPhone, which it does - but only for a test user accouunt. If I try to access OWA with the actual user's credentials I keep getting a HTTP 404 (file not found) error. If I configure the iPhone to synch using Exchange, it just replies back with "server connection failed", whether I try the test user's credentials or the actual users. It does display the certficate message which I click Accept, then the 404 error appears. any pointers on this would be much appreciated!

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Be sure you have the latest patches and application roll-ups on the Exchange server. Is this working on any other device like a Windows Mobile 6? Are you using ISA or anything to publish OWA? That is best practice. Take a look at the IIS logs on the server and the firewall logs. See if there are any messages there that may help identify where the traffic is failing.

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  • Wrobinson
    You need to figure out the difference between the test user and the actual user, which is likely to boil down to permissions. Checking OWA from an iPhone is for all intents and purposes, not different from checking it in a Web browser. Mobile devices typically do not handle certificate errors very well. You certainly will not be able to click around it using WM based devices. You need to resolve this by ensuring that the root CA is trusted and that the URL used to connect to the Exchange Server is the common name used in the certificate. Check accessibility from other mobile devices as recommended by Labnuke regarding the Exchange ActiveSync issue. This will let you know if it is device or system related.
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  • Kodyleonard
    This sounds similar to what we ran into, but this helped: http://bluescreensolutions.blogspot.com/2010/01/how-to-make-iphones-work-with-exchange.html
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  • Bahdussy76
    I believe you need to have an SSL Cert installed on the Server in order for the IPhone to receive emails with Exchange
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