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No messages downloaded to iPhone from SBS 2003/Exchange 2003

Posted on 2009-05-13
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Last Modified: 2012-05-06
I have a customer with SBS 2003, SP2 and Exchange Server 2003, SP2 and one iPhone 3G user. IMAP is enabled, ports are pinholed through the firewall and router. The customer is using a GoDaddy certificate. I have verified all the IMAP settings I can find in Exchange MMC against a working server system that iPhones work with. I have not been through the IIS settings to compare them as yet, but have reviewed them against all the information I can find for correctness. I can access the user's e-mail through the internet and internally using Outlook Express with IMAP just fine. The iPhone attempts to connect, lists the e-mail folders for the user, but never downloads any mail. I have tested the iPhone on another server that works with other iPhones with a different user and it worked fine. So - iPhone is verified, Outlook Express/IMAP works, any ideas on what to check next? After reading at least a hundred articles, I haven't come up with a solution.
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Question by:bdevance
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Expert Comment

by:Probity
ID: 24381410
iPhones and Exchange are often a bit finicky.  Do you allow OWA from your exchange server?  Sometimes the best medicine is to set the iPhone up via OWA to exchange instead of POP or IMAP.  That said, POP is another option your organization may consider if you have consistent IMAP problems.
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by:LinkNJ
ID: 24381656
I am fairly certain that the default Exchange setup in the updated OS on the IPHONE uses Outlook Web Access on the Exchange server.  This being said, a good article to follow on how to setup the Iphone is here:
http://blog.fosketts.net/2008/07/10/how-to-set-up-iphone-exchange-activesync/
I admittaly have only setup about a dozen Iphone and Windows Mobile devices to SBS servers but they are all working.  So if you setup your firewall and be sure to run the E-mail and Internet Connection Wizard (sometimes known as CEICW - More info on MS web site HERE) that should get SBS ready to use Outlook Web Access (OWA.)  Good luck, Rob.
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by:JohnGerhardt
ID: 24386867
As the previous two experts have stated you are going to be much better to use exchange active sync rather than IMAP..
Setting it up isn't that challenging and there are plenty of questions here on EE already on how to do it.
Have a look at www.testexchangeconnectivity.com and run the active sync test. This is a great way of checking that you are up and running correctly as the iPhone is a poor dianostic tool, when things go wrong..
 
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Author Comment

by:bdevance
ID: 24388462
Thanks for the suggestions. In my quest to be specific, perhaps I was not. I am not setting up IMAP per se on the iPhone - I'm using activesync by selecting exchange server as the mail connection type. I was trying to verify that I do not have an IMAP issue by testing with Outlook Express. I ran the test suggested by JohnGerhardt and it completed successfully. BTW - that is a phenomenal tip -- great tool!
With that -- still looking for ideas. I'm on-site at the moment and plan to take a futher look at IIS settings.
Thanks to all.
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by:LinkNJ
ID: 24388664
Are you using a public ssl certificate? If not, that may be your answer as I am pretty sure Iphone requires it.  www.certicatesforexchange.com is what I use.  sorry for short answer, on the phone, let me know if you need more details. Good luck, Rob.
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by:LinkNJ
ID: 24391009
I don't think there is a way to edit a post, but if I could I would correct the link above to https://certificatesforexchange.com/.  I apologize for the poor typing on my phone as I was in the car (not driving) at the time.  Good luck, Rob.
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Author Comment

by:bdevance
ID: 24401195
It appears to be directory permissions issues with the various virtual servers/directories used for sync, etc. I adjusted these to Integrated Windows and Basic authentication and mail began to flow. While the inbox is working correctly and send works correctly, some folders still do not populate with e-mail and so far the calendar and contacts have not synced.
More later - still monitoring progress and checking permissions, etc.
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by:JohnGerhardt
ID: 24401526
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bdevance earned 0 total points
ID: 24548243
It looks like we're going to back-burner this until the fall when the customer wants to move to Server 2008 & Exchange 2007. It turns out that the previous company servicing this customer had "tinkered" with IIS and all its services to the point of making it difficult to get back to a known starting place. Meantime, the iPhone user is using IMAP for e-mail and desktop/iTunes sync for contacts & calendar.
Thanks for all help and suggestions.
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by:JohnGerhardt
ID: 24562333
Ok, Thanks for the update...
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