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Some iPhone Users Can't Connect to Exchange 2013 Now

Posted on 2016-11-02
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Last Modified: 2016-11-23
We recently did an Exchange migration from 2007 to 2013 and everything seemed to be working fine. I had Exchange 2013 running for a week with no one having issues and shutdown the 2007 server for a day to ensure nothing was relying on it. I uninstalled 2007 yesterday and everything seemed to be okay.
However, some iPhones are having issues connecting to Exchange from their phones now. They get a message that says "Cannot Get Mail - The connection to the server failed."
This is only apparently happening on a few iPhones in our organization and people with Android are having no issues. On one of the devices I was able to attach my email to their phone and it worked but won't work with their credentials. I'm at a loss as to what could be causing this.

I have already tried toggling 'Exchange ActiveSync', removed the mobile device from their Exchange profile, and made sure they have Inherited Permissions in AD. None of which are helping. I have also Reset Network Settings on the iPhone and tried removing/adding the account again with no success either.

Any suggestions?
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Question by:Joe Lowe
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18 Comments
 
LVL 18

Expert Comment

by:Kyle Santos
ID: 41870959
Hi Joe,

Sorry to hear about the problem you're having.  I wrote a troubleshooting article around issues described like yours.
https://www.experts-exchange.com/articles/19119/iPhone-Samsung-Will-Not-Connect-or-Sync-To-Microsoft-Exchange-Server.html

Give it a read and let me know if this helps or not.
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LVL 17

Expert Comment

by:Jason Crawford
ID: 41870963
By any chance are the affected users Domain Admins?  Are you passing an ExRCA test?

https://testconnectivity.microsoft.com/
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Author Comment

by:Joe Lowe
ID: 41870979
Hmmm...this is interesting. Looks like I got this message at the bottom. Everything else passed except for the attached.
How is email working on my phone and others then? What would fix that?
Exchange500Err.docx
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LVL 17

Expert Comment

by:Jason Crawford
ID: 41870982
For the user account you're testing:

1. Open Active Directory Users and Computers.
2. On the menu at the top of the console, click View > Advanced Features.
3. Locate and right-click the mailbox account in the console, and then click Properties.
4. Click the Security tab.
5. Click Advanced.
6. Make sure that the check box for "Include inheritable permissions from this object's parent" is selected.
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Author Comment

by:Joe Lowe
ID: 41870985
Jason, that was one of the first things I checked and it is currently on. I have also tried disabling and re-enabling. I did get an error on the ExRCA test though. These are not for domain admins, these are regular users having the issue.
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Expert Comment

by:Jason Crawford
ID: 41870989
Ok well that's the first thing I go to in situations like these.  What type of authentication settings are applied to the ActiveSync vDir?  Do you have any redirection configured in IIS?
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LVL 17

Expert Comment

by:Jason Crawford
ID: 41870991
I've seen throttling produce similar behavior, and Apple is known for opening connections in Exchange and never closing them.
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LVL 17

Expert Comment

by:Jason Crawford
ID: 41870999
This article address a possible misconfigured web.config file:

http://msexchangeguru.com/2013/09/24/e2013remote-server500internalservererror/
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Author Comment

by:Joe Lowe
ID: 41871161
For Authentication we have:
SSL enabled True:
Basic Authentication: has a checkbox
Client Certificate Authentication: Ignore client certificates

I don't believe I see any redirection in IIS.

The last link provided may not apply to me since those commands don't seem to work on our Exchange.
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Author Comment

by:Joe Lowe
ID: 41871172
Update:
I may have not entered the correct information in. For my username I used the format Username@contoso.com instead of contoso/username. I got the attached results this time.
Exchange500Err.docx
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Accepted Solution

by:
Joe Lowe earned 0 total points
ID: 41871215
Another Update:
I had one of the infected phones install Outlook (the app, not the Apple provided Mail app), and that seemed to work with no issues.
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LVL 17

Expert Comment

by:Jason Crawford
ID: 41871304
Really...good to know, Joe.  What iOS version are you running on that iPhone?
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Assisted Solution

by:Joe Lowe
Joe Lowe earned 0 total points
ID: 41872327
The iPhone I was working with is now on the newest iOS version which is 10.1.1. Others may be on an older version.
It's interesting that the Outlook app works but the Mail app for iPhone does not. We have considered just making the Outlook app a standard moving forward to not have to worry about cross-platform compatibility.
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LVL 17

Expert Comment

by:Jason Crawford
ID: 41872564
Yea good luck with that.  Apple users are a loyal breed
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LVL 18

Expert Comment

by:Kyle Santos
ID: 41872609
Did you already try the common answers in the article I provided?

That is interesting that the Outlook app would work, but not the Mail app.
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Author Comment

by:Joe Lowe
ID: 41872650
Oh yes, I have noticed that Jason. Loyal Breed is an accurate statement.

Kyle, I did check out your article yesterday. The only thing we had not done was turn on/off Airplane mode. I'll try that if I encounter another iPhone but we did do multiple restarts, perform the iOS update that was available, and reset network settings on the one I troubleshot.
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LVL 18

Expert Comment

by:Kyle Santos
ID: 41872717
OK cool, thanks for letting me know.  Then I'm out of ideas and will definitely glean from this discussion to add into my article for future users.  Cheers.
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Author Closing Comment

by:Joe Lowe
ID: 41898867
Appears to be the workaround. Will try a CU later.
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