Iphone and SBS 2003

Welcome to my Exchange 2003 / Activesync article:
https://www.experts-exchange.com/articles/Software/Server_Software/Email_Servers/Exchange/Exchange-2003-Activesync-Connection-Problems-FAQ.html
The nuts and bolts to getting Activesync working on an Exchange 2003 server : )

Have you installed the OWA certificate on the Iphone? If not this is the first thing you need to do, easiest way of doing this is by sending the owa certificate to a yahoo/ gmail account and configuring the iphone to pick this up first, once you can see the mail on the phone click on the attached cer file and it should prompt you to install the certificate. Once installed, go back to email settings and then perform the exchange activesync setup, quick guide can be found here http://support.apple.com/kb/HT2480, remember to input the domain name as domain.local, it will then prompt for a exchange server name, at which point you enter the exchange server name and hopefully it should sync without any issue. Once done you can delete the other email account you setup to pull the certificate across.

Installing certificate on iPhones is not necessary.  Windows Mobiles are different unless the cert is a 3rd party cert.  You just click Accept on an iPhone and off it goes.

Alan,

I disagree, without the certificate it fails to sync without prompting you to accept the certificate everytime , I have configured around 30 iPhones and all have required the self signed SBS certificate to be installed, the only way round this is to either use a public certificate and then there is no need to install the cert file or if you do want to use the self signed certificate and not be prompted every time then installing the cer file on the iphone rectifies the problem.

I followed the directions by delmc, and when i run the test i get the following results.
 Testing Exchange ActiveSync  
  Exchange ActiveSync test Failed
   Test Steps
   Attempting to resolve the host name mail.reindeerauto.com in DNS.
  Host successfully resolved
   Additional Details
  IP(s) returned: 69.39.146.170  
 
 Testing TCP Port 443 on host mail.reindeerauto.com to ensure it is listening and open.
  The port was opened successfully.
 Testing SSL Certificate for validity.
  The certificate passed all validation requirements.
   Test Steps
   Validating certificate name
  Successfully validated the certificate name
   Additional Details
  Found hostname mail.reindeerauto.com in Certificate Subject Common name  
 
 Testing certificate date to ensure validity
  Date Validation passed. The certificate is not expired.
   Additional Details
  Certificate is valid: NotBefore = 6/16/2006 12:17:23 AM, NotAfter = 6/16/2011 12:17:23 AM"  
 
 
 
 Testing Http Authentication Methods for URL https://mail.reindeerauto.com/Microsoft-Server-Activesync/ 
  Http Authentication Methods are correct
   Additional Details
  Found all expected authentication methods and no disallowed methods. Methods Found: Basic  
 
 Attempting an ActiveSync session with server
  Errors were encountered while testing the ActiveSync session
   Test Steps
   Attempting to send OPTIONS command to server
  OPTIONS response was successfully received and is valid
   Additional Details
  Headers received: Connection: Keep-Alive
MicrosoftOfficeWebServer: 5.0_Pub
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: Fri, 09 Apr 2010 14:16:11 GMT
Server: Microsoft-IIS/6.0
X-Powered-By: ASP.NET

 
 
 Attempting FolderSync command on ActiveSync session
  FolderSync command test failed
   Tell me more about this issue and how to resolve it
   Additional Details
  Exchange ActiveSync returned an HTTP 500 response.  
 
 
 
 
 

You'll find the answer to that in my article - KB883380 method 2.

I followed the directions in method 2 and got the exact same results when i re-tested.

 Testing Exchange ActiveSync  
  Exchange ActiveSync test Failed
   Test Steps
   Attempting to resolve the host name mail.reindeerauto.com in DNS.
  Host successfully resolved
   Additional Details
  IP(s) returned: 69.39.146.170  
 
 Testing TCP Port 443 on host mail.reindeerauto.com to ensure it is listening and open.
  The port was opened successfully.
 Testing SSL Certificate for validity.
  The certificate passed all validation requirements.
   Test Steps
   Validating certificate name
  Successfully validated the certificate name
   Additional Details
  Found hostname mail.reindeerauto.com in Certificate Subject Common name  
 
 Testing certificate date to ensure validity
  Date Validation passed. The certificate is not expired.
   Additional Details
  Certificate is valid: NotBefore = 6/16/2006 12:17:23 AM, NotAfter = 6/16/2011 12:17:23 AM"  
 
 
 
 Testing Http Authentication Methods for URL https://mail.reindeerauto.com/Microsoft-Server-Activesync/ 
  Http Authentication Methods are correct
   Additional Details
  Found all expected authentication methods and no disallowed methods. Methods Found: Basic  
 
 Attempting an ActiveSync session with server
  Errors were encountered while testing the ActiveSync session
   Test Steps
   Attempting to send OPTIONS command to server
  OPTIONS response was successfully received and is valid
   Additional Details
  Headers received: Connection: Keep-Alive
MicrosoftOfficeWebServer: 5.0_Pub
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: Fri, 09 Apr 2010 15:18:40 GMT
Server: Microsoft-IIS/6.0
X-Powered-By: ASP.NET

 
 
 Attempting FolderSync command on ActiveSync session
  FolderSync command test failed
   Tell me more about this issue and how to resolve it
   Additional Details
  Exchange ActiveSync returned an HTTP 500 response.
 
 
 
 
 

Okay - please follow the HTTP 500 Error: section in my article after the KB883380 fix and follow the suggestions.
https://www.experts-exchange.com/articles/Software/Server_Software/Email_Servers/Exchange/Exchange-2003-Activesync-Connection-Problems-FAQ.html 
If that does not work and you have checked all the other settings, it's time to call Microsoft I'm afraid.

I followed the beginning of that solution and I never received an OK from the test, and the solution on continues if you received an OK.

Hi,

Refer this article:
http://support.microsoft.com/kb/886346/

Also check the application event log and post the error event description related to ActiveSync.

I hope this helps,
Shree

Ah - the joy of Google!