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I am trying to get our iPhones connected via ActiveSync with Exchange Server 2003 SP2.

I have an SSL cert and OWA is working fine using HTTPS. I have 443 open on the firewall and pointed at the single Exchange server. The cert is for When I try to connect the iPhones it just continues to ask for a password and will eventually come back with an error that it could not get mail.

I have IMAP working fine on the iPhone but would like to shut down the service and just use ActiveSync. I don't have an iPhone to test with so I have to continue to bother users to try new options of settings on the iPhone, which is getting to be a little embarassing. Everthing I am reading says that once 443 this open with a cert this is a no brainer to get it connected.

I am unsure at this point if I have a configuration issue with the way I am putting in the settings on the iPhone or if there is another setting I am missing on Exchange or the firewall.

Any ideas?

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I failed to mention we have a Sonicwall firewall and a Baracuda spam filter. – Chad Sep 21 '09 at 0:28

Microsoft has a "tool" (in the form of a web site and robotic ActiveSync client) that might help you out: This will help you, especially, since you don't have your own ActiveSync client to test with.

I have yet to have an E2K3 installation of any age "just work" out of the box with ActiveSync. Typically I find things like SSL required on the "/exchange" directory, or the "Negotiate" authentication provider not being set, etc.

Microsoft offers some general guidance at:

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Thanks for the info. I found this article and I am making some progress. Instead of getting a system error when trying to connect to OMA via IE, I am now getting to my mailbox. Not quite sure why I needed to deny access for my exchange server to the new virtual directory I created for OMA or why I couldn't use the default OMA virtual directory, but it seems to be working. Will test on an iPhone when I can get my hands on one. Thank you. – Chad Sep 21 '09 at 1:19
+1 that online tool provided by Microsoft is very helpful. I once discovered that authorization on the IIS web had too many unnecessary options activated. – splattne Sep 21 '09 at 8:30

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