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Problems configuring iPhone to use ActiveSync to Exchange 2003 SP2

Posted on 2011-02-23
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Last Modified: 2012-08-14
Experts,

I am trying to configure an iPhone's ActiveSync to send/receive mail from Exchange 2003 SP2 box; while all the settings test OK, the user cannot send/receive mail from the mobile device.

I ran a Connectivity Analyzer Test using MS' tool and these are the results:

Please help!
ExRCA is testing Exchange ActiveSync.
 	Exchange ActiveSync was tested successfully.
 	
	Test Steps
 	
	Attempting to resolve the host name mail.newcodistributors.com in DNS.
 	The host name resolved successfully.
 	
	Additional Details
 	IP addresses returned: 64.80.5.42
	Testing TCP port 443 on host mail.newcodistributors.com to ensure it's listening and open.
 	The port was opened successfully.
	Testing the SSL certificate to make sure it's valid.
 	The certificate passed all validation requirements.
 	
	Test Steps
 	
	Validating the certificate name.
 	The certificate name was validated successfully.
 	
	Additional Details
 	Host name mail.newcodistributors.com was found in the Certificate Subject Common name.
	Validating certificate trust for Windows Mobile devices.
 	The test passed with some warnings encountered. Please expand the additional details.
 	
	Additional Details
 	The certificate is only trusted on Windows Mobile 5.0 with the Messaging and Security Feature Pack and later versions. Windows Mobile 5.0 devices won't be able to sync. Root = E=info@valicert.com, CN=http://www.valicert.com/, OU=ValiCert Class 2 Policy Validation Authority, O="ValiCert, Inc.", L=ValiCert Validation Network
	Testing the certificate date to confirm the certificate is valid.
 	Date validation passed. The certificate hasn't expired.
 	
	Additional Details
 	The certificate is valid. NotBefore = 8/26/2009 6:47:49 PM, NotAfter = 6/12/2013 6:29:02 PM
	Checking the IIS configuration for client certificate authentication.
 	Client certificate authentication wasn't detected.
 	
	Additional Details
 	Accept/Require Client Certificates isn't configured.
	Testing HTTP Authentication Methods for URL https://mail.newcodistributors.com/Microsoft-Server-Activesync/.
 	The HTTP authentication methods are correct.
 	
	Additional Details
 	ExRCA found all expected authentication methods and no disallowed methods. Methods found: Basic
	An ActiveSync session is being attempted with the server.
 	Testing of an Exchange ActiveSync session completed successfully.
 	
	Test Steps
 	
	Attempting to send the OPTIONS command to the server.
 	The OPTIONS response was successfully received and is valid.
 	
	Additional Details
 	Headers received: Pragma: no-cache
Public: OPTIONS, POST
Allow: OPTIONS, POST
MS-Server-ActiveSync: 6.5.7638.1
MS-ASProtocolVersions: 1.0,2.0,2.1,2.5
MS-ASProtocolCommands: Sync,SendMail,SmartForward,SmartReply,GetAttachment,GetHierarchy,CreateCollection,DeleteCollection,MoveCollection,FolderSync,FolderCreate,FolderDelete,FolderUpdate,MoveItems,GetItemEstimate,MeetingResponse,ResolveRecipients,ValidateCert,Provision,Search,Notify,Ping
Content-Length: 0
Date: Wed, 23 Feb 2011 21:43:28 GMT
Server: Microsoft-IIS/6.0
X-Powered-By: ASP.NET

	Attempting the FolderSync command on the Exchange ActiveSync session.
 	The FolderSync command completed successfully.
 	
	Additional Details
 	Number of folders: 25
	Attempting the initial sync to the Inbox folder. This initial sync won't return any data.
 	The Sync command completed successfully.
 	
	Additional Details
 	Status: 1
	Attempting to test the GetItemEstimate command for the Inbox folder.
 	ExRCA successfully received the GetItemEstimate response from the server.
 	
	Additional Details
 	Estimate: 98 messages
	Attempting to test synchronization of the Inbox folder.
 	The Sync command completed successfully.
 	
	Additional Details
 	Number of items synchronized: 98

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Question by:Newco
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8 Comments
 
LVL 76

Expert Comment

by:Alan Hardisty
ID: 34965299
The test results show a successful test.  What problems are you having specifically?
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LVL 1

Expert Comment

by:goodguy8
ID: 34965305
have you tried using the default ports for your mail on iphone. 110 and 25 with ssl off?
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 34965309
@goodguy8 - Activesync doesn't use SMTP / POP3 - it uses HTTPS (TCP Port 443).
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Author Comment

by:Newco
ID: 34965467
@alanhardisty: user authenticates fine but cannot send/receive mail. There is a warning that says SSL can only be used by Windows Mobile 5.0.

@goodguy8 and @alanhardisty: iPhone's ActiveSync uses secure imap4 (TCP Port 993).
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 34965506
>> There is a warning that says SSL can only be used by Windows Mobile 5.0. <<

You are using an iPhone so the warning is not relevant.

>> iPhone's ActiveSync uses secure imap4 (TCP Port 993) <<

Not correct - Activesync uses TCP Port 443 with SSL enabled and TCP Port 80 without SSL enabled.

What happens when they try to send mail?

Do they not get their calendar / contacts / mail sucked down to their iPhone?
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Accepted Solution

by:
Newco earned 0 total points
ID: 34965598
Thanks for the clarification; FYI, there was no synchronization to any of the user's folders.

The problem is now fixed! I rebooted the phone - that's the only thing that was left after configuring the phone and now it works.

Thank you Guys!
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LVL 76

Expert Comment

by:Alan Hardisty
ID: 34965633
Glad it was a simple fix.  Everything checked out okay so it had to be something non-server related.

Can't say I have ever had to reboot an iPhone after configuring it, but either way - great that you are working.

Alan
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Author Closing Comment

by:Newco
ID: 34995560
I resolved my own problem!
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