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iPhone calendar syncing problem

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Last Modified: 2012-05-08
Hello,

I have a user who is sometimes missing calendar appointments on their iPhone.  Their iPhone is hooked up to an Exchange account via Active Sync.  I thought at first the user was deleting it from their Outlook or iPhone, but I finally saw the problem today. The calendar item was in the users Outlook but not on his iPhone.  Every other appointment I looked at was sync'd up fine.  I was able to add new appointments to both iPhone and Outlook just fine.  I finally turned off the calendar sync on the iPhone and turned it back on.  Once I did the missing appointment re-appeared.  Any ideas what could be going on?  I tried to replicate the problem but I am unable to replicate it.

David  
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Alan HardistyCo-Owner
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Top Expert 2011

Commented:
Can you check to see if the appointment appears in OWA.  OWA accesses live data on the server and Outlook may not be replicating to the server properly.
If all seems well, please create an appointment via OWA and see if it syncs.  If it does, do the same on the iPhone and see if it syncs with OWA (don't forget to refresh OWA).
If that all works, then the problem is with Outlook.
If OWA / iPhone fails to sync, the problem is with the iPhone.
Please advise where it goes wrong.
Henry ElpBoss

Author

Commented:
The appointment does appear in OWA.  I also added appointments in OWA and the iPhone and the respective appointments appeared on both.  Are you sure the problem is with Outlook?  The appointment did appear on the iPhone after I turned the calendar on the iPhone off and on.  

David
Alan HardistyCo-Owner
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Top Expert 2011

Commented:
Yes - If OWA and the phone sync happily, then that can only be an Outlook problem.
If you are in cached Exchange Mode - close Outlook, delete the .OST file and then open Outlook.  It will suck everything down from the server and should be okay.
Worst case, delete the profile, delete the .OST and then set the profile up again.
If that fails, detect & repair outlook (2003) or Help Office Diagnostics for 2007.

Commented:
There are known issues with the iPhone and Outlook calenders.  Check it out:
http://www.slipstick.com/problems/iphonesync.asp

That is just the tip of the iceberg.  Apple has not perfected the calendar on the iphone to play nicely with exchange yet.  Or maybe it is the other way around.  In any case, there are issues.
Henry ElpBoss

Author

Commented:
Thanks for the reply wdurrett.  I don't think that hotfix will work however as the calendar item shows up in Outlook but not on the iPhone.  
Alan HardistyCo-Owner
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Top Expert 2011

Commented:
wdurrett - Not sure where you are getting your info from but I have an iPhone and so do many of my customers and they all sync happily with my Exchange server.
I also know many others who use them without problems.  Just yesterday I got one working for a new customer who did not have it working for 3 months and was told it would not work by people such as the head of IT for a large well-known company dealing in financial information!

Commented:
There is other information on that page for all types of sync problems - including links to Apple's KB concerning sync issues.

Commented:
I am not saying it "won't" work.  I simply stated there are issues.  If you do not agree with that, you may want to check Apple's KB, Microsoft's KB and numerous other message boards where issues have been identified.  Use google.

I have all iPhones working correctly in my environment, but I know of several places where it has been an issue.  All the issues can be solved, but the fact of the matter is that iPhones do not sync 100% of the time perfectly.
Alan HardistyCo-Owner
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Top Expert 2011

Commented:
Sure - nothing is ever 100% straight away, but this is usually as a result of bad / wrong configuration.

Commented:
Hey i have few info for you if this issue is for all the ActiveSync users on that server. If it is only for one Iphone user please ignore this Comment.

If it is for all the users in that server then we might have to look at one more thing on the server.
Check whether the DLL files on the server are up to date. If it is not then we will face these issues.

For example:
Massync.dll (Which you can find under the Bin folder) is responsible for the ActiveSync to work. Now if this DLL file's version is not up to date then we will have this issue. So you could install the hotfix to upgrade the DLL file

We do have Hotfix for updating the store.exe version and all related version even that has to be done so that the store and the device are up to date and then it should work fine with out any issues.
Henry ElpBoss

Author

Commented:
As far as I can tell eddie, this is just for 1 user.  
Alan HardistyCo-Owner
CERTIFIED EXPERT
Top Expert 2011

Commented:
If it is just for one user, have you reset the iPhone and setup the sync again?
Henry ElpBoss

Author

Commented:
We have tried re-syncing.  Furthermore we have even tried a new device as his old iPhone broke.  It happened on both devices so it leads me to believe it is something with Exchange Active Sync on our Exchange server.  

I was looking through our logs on the Exchange Server and found this error message:

Event Type:      Error
Event Source:      Server ActiveSync
Event Category:      None
Event ID:      3005
Date:            11/15/2009
Time:            6:25:52 PM
User:            doman\username
Computer:      exchange server name
Description:
Unexpected Exchange mailbox Server error: Server: [newman.carlsoncapital.com] User: [user email address] HTTP status code: [500]. Verify that the Exchange mailbox Server is working correctly.

For more information, see Help and Support Center at http://go.microsoft.com/fwlink/events.asp.

I did a a little googling and found this MS KB article:  http://support.microsoft.com/kb/817379
Which seems similar to my problems but that KB article didn't have my exact Event ID so I don't think it applies to me.  

Thanks for all the replies so far.
David
Alan HardistyCo-Owner
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Top Expert 2011

Commented:
Can you try the test tool at https://testexchangeconnectivity.com or download the app from https://store.accessmylan.com/main/diagnostic-tools
Once run, please post the results and remove any domain info you don't want to be publically available.
Henry ElpBoss

Author

Commented:
Testing Exchange ActiveSync
       Exchange ActiveSync test Failed
       
      Test Steps
       
      Attempting to resolve the host name xxxxxxxx in DNS.
       Host successfully resolved
       
      Additional Details
        IP(s) returned: 174.46.xx.xxx
      Testing TCP Port 443 on host xxxxxx to ensure it is listening and open.
       The port was opened successfully.
      Testing SSL Certificate for validity.
       The SSL Certificate failed one or more certificate validation checks.
       
      Test Steps
       
      Validating certificate name
       Successfully validated the certificate name
       
      Additional Details
        Found hostname xxxxxxx in Certificate Subject Common name
      Validating certificate trust for Windows Mobile Devices
       Certificate trust validation failed
        Tell me more about this issue and how to resolve it
       
      Additional Details
        The certificate chain did not end in a trusted root. Root = OU=VeriSign Trust Network, OU="(c) 1998 VeriSign, Inc. - For authorized use only", OU=Class 3 Public Primary Certification Authority - G2, O="VeriSign, Inc.", C=US

We have a certificate from Verisign matching name we put into our mobile devices... some reason it doesn't like it?  
Alan HardistyCo-Owner
CERTIFIED EXPERT
Top Expert 2011

Commented:
As it is a 3rd party SSL certificate, I would take this up with Verisign as the certificate could be incorrectly setup.
Once you have an SSL cert that works, please try the tests again.
Boss
Commented:
This one is on us!
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Alan HardistyCo-Owner
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Top Expert 2011

Commented:
Cannot comment on that - ISA is not my area of expertise I'm afraid.

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