OWA Calendar item generating an HTTP/1.1 500 Internal Server Error

We have had a problem over the past few months where Motorola Droid phones
do not properly get all the calendar items when they sync. They always
miss a couple. Recently we have discovered that these appointments
that do not sync also give a HTTP/1.1 500 Internal Server Error when
they are viewed in OWA. But others are viewable and email works fine
as well..This only happens on a couple appointments for a couple

Windows 2k3 Standard
Exchange 2003 SP2

Windows 7 ultimate
ie 8
Michael SoleDirector of SupportAsked:
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a) Lets get more detailed Error reports

Test for Exchn ActiveSync
and Exch ActiveSync autodiscover

please post back results here (copy-paste)

b) You should give this a read. This a comprehensive article on EAS and types of errors and what to do about it.

Hope this helps.

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Michael SoleDirector of SupportAuthor Commented:
Here are the test results:

ExRCA is testing Exchange ActiveSync.  Exchange ActiveSync was tested successfully.  
     Test Steps
          Attempting to resolve the host name exchange01.gold-mobile.net in DNS.
     Host successfully resolved
          Additional Details
     IP(s) returned:

     Testing TCP Port 443 on host to ensure it is listening and open.
     The port was opened successfully.
     ExRCA is testing the SSL certificate to make sure it's valid.
     The certificate passed all validation requirements.
          Test Steps
          The certificate name is being validated.
     Successfully validated the certificate name
          Additional Details
     Found hostname  in 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
     Certificate is only trusted on Windows Mobile 6.0 and later. Windows Mobile 5.0 and 5.0 + MSFP devices will not be able to sync. Root = OU= 2 Certification Authority, O=".", C=US

     The certificate date is being confirmed to ensure the certificate is valid.
     Date validation passed. The certificate hasn't expired.
          Additional Details
     Certificate is valid: NotBefore =, NotAfter = "

     The IIS configuration is being checked for client certificate authentication.
     Client certificate authentication wasn't detected.
          Additional Details
     Accept/Require Client Certificates not configured.

     Testing Http Authentication Methods for URL https://exchange/Microsoft-Server-Activesync/
     The HTTP authentication methods are correct.
          Additional Details
     Found all expected authentication methods and no disallowed methods. Methods Found: Basic

     An ActiveSync session is being attempted with the server.
     Testing an ActiveSync session completed successfully
          Test Steps
          ExRCA is attempting to send the OPTIONS command to the server.
     OPTIONS response was successfully received and is valid
          Additional Details
     Headers received: Pragma: no-cache
MS-Server-ActiveSync: 6.5.7654.7
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: Fri, 23 Jul 2010 18:24:11 GMT
Server: Microsoft-IIS/6.0
X-Powered-By: ASP.NET

     ExRCA is attempting the FolderSync command on the Exchange ActiveSync session.
     The FolderSync command completed successfully.
          Additional Details
     Number of Folders: 35

     ExRCA is 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

     ExRCA is attempting to test the GetItemEstimate command for the Inbox folder.
     Successfully received GetItemEstimate Response from Server
          Additional Details
     Estimate: 1231 messages

     ExRCA is attempting to test synchronization of the Inbox folder.
     The Sync command completed successfully.
          Additional Details
     Number of items synchronized: 512

So here is what I have found out... This happens when a user accepts and invitation for a calendar event on iPhone or iPad. The event shows up fine at first, but as soon as they "accept" using an iPhone (This is an iPhone 4) it gets corrupted and the "HTTP/1.1 500 Internal Server Error" in OWA.

What I don't know is whether it is an iPhone issue that is or will be fixed in future iOS updates or something that needs to be fixed on Exchange side. I would have to upgrade that iPhone to the latest release and test it again.

[SBS 2003 SP2 with Exchange 2003 SP2]
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