Question

New SSL Certificate breaks iPhone access to Exchange 2003

Asked by: parimp

I have been running SBS2003 with Exchange and iPhones successfully for about 6 months. Our OWA SSL Certificate expired and I revoked it and created a brand new certificate. The installation of the new SSL certificate went great on the server and OWA access was promptly restored.  The new certificate is the $29 one from Godaddy and I have followed all instruction to install correctly on the Server.

All remote machines and internal machines can access OWA and you can access OWA on the iphone using Safari.

However, for the life of me I cannot get any email to download from the exchange server (which was working fine yesterday) I have tried rebuilding the exchange virtual directories, removing the profile on the iphone for the SSL cert. I have tried copying the new cert to another email account on the iphone and installing it but the result it all the same.

I get no error when trying to access the emails, it just looks like its going to connect and then says updated. No folders are present except the inbox. Recently I have been getting CANNOT GET MAIL message on iPhone saying The connection to the server failed.

Can anyone help with this? My gut feeling is that there is some problem with Exchange Activesync and the new certificate, but then again I havent had any success in 8 hours!!??

Thanks in advance
Ryon.

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Asked On
2009-08-27 at 22:18:07ID24688869
Topics

iPhone

,

Exchange Email Server

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Answers

 

by: demazterPosted on 2009-08-27 at 22:30:31ID: 25205124

Download the configuratio tool and install the new certificate on the phone: http://www.theiphoneblog.com/2008/07/10/apples-releases-iphone-config-utilities/

 

by: demazterPosted on 2009-08-27 at 22:33:41ID: 25205133

Check your configuration against this: http://support.microsoft.com/kb/937635

Also check this is not happening: http://support.microsoft.com/kb/957191

 

by: parimpPosted on 2009-08-28 at 00:20:27ID: 25205547

Hi Demazter, many thanks for the replies, I will only be able to test this now on monday, will post the responses then - its already friday night here :) - have a great weekend. Ryon

 

by: JohnGerhardtPosted on 2009-08-28 at 12:44:44ID: 25211014

Hi,

Can you try running the active sync test @ www.testexchangeconnectivity.com and post the results..

Hopefully this will point out what is going wrong..

 

by: parimpPosted on 2009-08-30 at 14:48:52ID: 25219553

Testing Exchange Activesync for host https://parimp.co.nz/Microsoft-Server-Activesync/
       Exchange Activesync test Failed
      Test Steps
       
      Attempting to Resolve the host name parimp.co.nz in DNS.
       Host successfully Resolved
      Additional Details
       IP(s) returned: 203.97.205.12
      Testing TCP Port 443 on host parimp.co.nz to ensure it is listening/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 parimp.co.nz in Certificate Subject Alternative Name entry
      Validating certificate trust for Windows Mobile Devices
       The test passed with some warnings encountered. Please expand additional details.
      Additional Details
       Certificate is only trusted on Windows Mobile 5.0 AKU2 (MSFP) and later. Windows Mobile 5.0 devices will not be able to sync. Root = E=info@valicert.com, CN=http://www.valicert.com/, OU=ValiCert Class 2 Policy Validation Authority, O="ValiCert, Inc.", L=ValiCert Validation Network
      Testing certificate date to ensure validity
       Date Validation passed. The certificate is not expired.
      Additional Details
       Certificate is valid: NotBefore = 8/27/2009 1:08:06 AM, NotAfter = 8/27/2010 1:08:06 AM
      Testing Http Authentication Methods for URL https://parimp.co.nz/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: 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: Sun, 30 Aug 2009 21:52:57 GMT
Server: Microsoft-IIS/6.0
X-Powered-By: ASP.NET

      Attempting FolderSync command on ActiveSync session
       FolderSync command test failed

 

by: parimpPosted on 2009-08-30 at 16:45:41ID: 25219875

here is the result of the log from the iphone configuration program, still the same, says updated but no folders or emails.

 

by: parimpPosted on 2009-08-30 at 19:12:50ID: 25220239

This is from the ESM on my server to confirm SP2 from what I have read.

Exchange System

Microsoft Corporation

Version: 6.5.7638.1

 

by: demazterPosted on 2009-08-30 at 23:00:28ID: 25220730

On the virtual directories in the directory security tab under IP restrictions remove any entries you have for ip addresses and set them all to "allow all except"

once done restart IIS

 

by: parimpPosted on 2009-08-31 at 01:27:51ID: 25221228

I have done that and restarted IIS and still it is the same, no folders or emails, this used to work fine last week!

 

by: demazterPosted on 2009-08-31 at 01:33:57ID: 25221247

Download the activesync test application from the AppStore on the iPhone, it's free and will give you a detailed log as to what is happening.

 

by: demazterPosted on 2009-08-31 at 01:35:10ID: 25221253

Do you have another phone you can try it on?
Have you removed the exchange account from the phone and re-created it?

 

by: parimpPosted on 2009-08-31 at 01:40:09ID: 25221277

yes i have done that and tried it on another phone, all 4 of our iphones cannot connect at present, since around friday. I just reran the connectivty tests and got one other error this time about "Testing Http Authentication Methods"

Test Details
Copy to Clipboard Expand/Collapse  
 Testing Exchange Activesync for host https://parimp.co.nz/Microsoft-Server-Activesync/
  Exchange Activesync test Failed
 Test Steps
   Attempting to Resolve the host name parimp.co.nz in DNS.
  Host successfully Resolved
 Additional Details
  IP(s) returned: 203.97.205.12  
 
 Testing TCP Port 443 on host parimp.co.nz to ensure it is listening/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 parimp.co.nz in Certificate Subject Alternative Name entry  
 
 Validating certificate trust for Windows Mobile Devices
  The test passed with some warnings encountered. Please expand additional details.
 Additional Details
  Certificate is only trusted on Windows Mobile 5.0 AKU2 (MSFP) and later. Windows Mobile 5.0 devices will not be able to sync. Root = E=info@valicert.com, CN=http://www.valicert.com/, OU=ValiCert Class 2 Policy Validation Authority, O="ValiCert, Inc.", L=ValiCert Validation Network  
 
 Testing certificate date to ensure validity
  Date Validation passed. The certificate is not expired.
 Additional Details
  Certificate is valid: NotBefore = 8/27/2009 1:08:06 AM, NotAfter = 8/27/2010 1:08:06 AM  
 
 
 
 Testing Http Authentication Methods for URL https://parimp.co.nz/Microsoft-Server-Activesync/
  The test passed with some warnings encountered. Please expand additional details.
   Tell me more about this issue and how to resolve it
 
 Additional Details
  The following authentication methods are enabled but are not allowed Authentication methods for this service. Methods: Negotiate, NTLM  
 
 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: 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: Mon, 31 Aug 2009 08:40:10 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.  
 
 
 
 
 
 

 

by: demazterPosted on 2009-08-31 at 01:48:58ID: 25221315

Exactly the same as here with the resolution being the post I posted earlier.
As long as all the virtual directories are configured as per the link in my first post this should work.

See here for similar questions with the resolutions being the same as the ones I have offered:

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_23566408.html
http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_24103243.html

also have a look here: http://support.microsoft.com/kb/817379

is there anything in the application event log?

 

by: parimpPosted on 2009-08-31 at 02:32:31ID: 25221455

I just went through this link again right now.. http://support.microsoft.com/kb/937635 and have restarted IIS and still no success. I am also getting an error in the application log event id 3031 when one of the iphones tries to connect

I have also gone through article http://go.microsoft.com/fwlink/?linkid=3052&kbid=817379 as mentioned below, but I must have missed something, I will recheck this article in the morning, its getting late here.

Event Type:      Error
Event Source:      Server ActiveSync
Event Category:      None
Event ID:      3031
Date:            31/08/2009
Time:            9:26:49 p.m.
User:            PIL\xxx
Computer:      PIL001
Description:
The mailbox server [PIL001.pil.local] does not allow "Negotiate" authentication to its [exchange] virtual directory. Exchange ActiveSync can only access the server using this authentication scheme.  For information about how to configure Exchange virtual directory settings, see Microsoft Knowledge Base article 817379, "Exchange ActiveSync and Outlook Mobile Access errors occur when SSL or forms-based authentication is required for Exchange Server 2003" (http://go.microsoft.com/fwlink/?linkid=3052&kbid=817379).   For information about how to properly configure IIS to support Kerberos and NTLM authentication, see Microsoft Knowledge Base article 215383, "How To Configure IIS to Support Both Kerberos and NTLM Authentication" (http://go.microsoft.com/fwlink/?linkid=3052&kbid=215383).  This issue may occur after installing Windows SharePoint Services on a server running Exchange Server 2003. For information about how to properly configure a server to run both Windows SharePoint Services and Exchange Server 2003, see Microsoft Knowledge Base article 823265, "You receive a "Page not found" error message when you use Outlook Web Access (OWA) to browse the Exchange Server 2003 client after you install Windows SharePoint Services" (http://go.microsoft.com/fwlink/?linkid=3052&kbid=823265).

 

by: parimpPosted on 2009-08-31 at 03:18:16ID: 25221629

demazter,

I have followed this article:

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_24103243.html

I then followed this part "If you are not using the settings as mentioned above, then you need to ensure the Exchange Virtual directory has "Windows Integrated Authentication" enabled under IIS Manager."

I enabled this and now the iphone is working, which is great!!!

Just curious, does this mean that the GoDaddy cert is not working on the iphone connections, just OWA? Is this setup secure?

Thank you so much for all your time on this. Really appreciated!!!
Ryon

 

by: demazterPosted on 2009-08-31 at 03:46:52ID: 25221745

If the iPhone is using SSL then it should be fine, the integrated authentication is just an authentication mechanism.

 

by: demazterPosted on 2009-08-31 at 03:51:30ID: 25221768

Not sure why that is but I will check and let you know.

 

by: demazterPosted on 2009-08-31 at 04:03:46ID: 25221831

At least you got it sorted.

 

by: parimpPosted on 2009-08-31 at 11:47:58ID: 31621579

There are so many settings that can affect this! Thanks demazter

 

by: parimpPosted on 2009-08-31 at 20:26:34ID: 25228361

Did your checks reveal anything else? Regards, Ryon

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