SSL Certificate For SBS 2008 and ISA 2006 causing problems with Activesync

Posted on 2009-05-15
Last Modified: 2012-05-07
I've read several solutions to this problem, but none seem to work.
Here is the problem.

I have sbs 2008 that runs exchange 2007.
I have an edge of network ISA 2006 server.

Everything is working correctly, except for activesync.

Mail is flowing fine, OWA works correct without any browser errors.

When I try to sync my windows mobile 6.1 phone with exchange, I get this support code 0x80072f0d "The security certificate on the server is not valid.  Contact your exchange Server Administrator or ISP to install a valid certificate on the server."

Obviously this is a problem with my godaddy SSL Cert.

I originally installed the godaddy certificate using the sbs 2008 wizard and then imported it into ISA.  Since reading I have went back and installed the certificate per these instructions
Since installing the certificate through that method, I have not changed anything on my ISA server.

So, assuming the certificate s my problem,  I guess I need to make sure that I have this certificate properly installed on my SBS box along with my ISA box.

Another issue may be that my certificate is for, when my owa is located at

Your help is greatly appreciated.

Question by:staub1981
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
  • 4
  • 2
  • 2
  • +2
LVL 65

Expert Comment

ID: 24399724
Did you install the intermediate certificates on the ISA server?

LVL 33

Expert Comment

by:Dave Howe
ID: 24400003
I have seen some mobile devices not have an appropriate CA already installed - but that's fine, usually you can extract them from your browser, place them on a webserver, and import them into the device that way.
LVL 24

Assisted Solution

by:Rajith Enchiparambil
Rajith Enchiparambil earned 250 total points
ID: 24401849
Looks like an improperly configured cert.

Create a test account and run the test in the Microsoft test site. See what it flags.
Office 365 Training for Admins - 7 Day Trial

Learn how to provision tenants, synchronize on-premise Active Directory, implement Single Sign-On, customize Office deployment, and protect your organization with eDiscovery and DLP policies.  Only from Platform Scholar.

LVL 33

Expert Comment

by:Dave Howe
ID: 24402468
I have had similar problems with certs that come with an "intermediate" certificate. normally if I put those on a webserver, browse to them in the mobile device, then select them, it imports them and in future validates correctly. sometimes supplying them with the original doesn't work - despite the fact the site serves them, the mobile device doesn't seem to have the ability to check a certificate chain not already in its keystore (admittedly, this is mostly on nokia s40 devices)

Author Comment

ID: 24403683
Thanks for the quick responses...

1.  Yes, I attempted to install them, it looked like it was right, but apparently didn't work.
2.  I've read about the mobile devices that don't have the CA's already installed, but I looked and my mobile device does have the godaddy class 2 listed.  Also, If I had to go to each mobile device and import it, that would be a pain.. If there was anyway to avoid that (including getting a different cert) I would prefer that.
3. is an awesome tool.  This is the problem is listed for me.

Connectivity Test Failed                                                                                                                                                 
 Testing Exchange Activesync for host                                                                                             
Exchange Activesync test

Test Steps                                                                                                                                                                                                                                                                                                                                                             Attempting to Resolve the host name in DNS.                                                                                                                                             
Host successfully Resolved                                                                                                                                            
Additional Details                                                                                                                                               IP(s) returned: 216.***.***.***
Testing TCP Port 443 on host to ensure it is listening/open.                                                                                                                                             
The port was opened successfully.                                                                                                                                                                                                                                                                                                                                                                                                
Testing SSL Certificate for validity.                                                                                                                                             
The SSL Certificate failed one or more certificate validation checks.                                                                                                                                                                                                                                                                                                                 
Additional Details                                                                                                                                               
A network error occurred while communicating with remote host:
 Exception Details:
 Message: The handshake failed due to an unexpected packet format.
 Type: System.IO.IOException
 Stack Trace:
 at System.Net.Security.SslState.StartReadFrame(Byte[] buffer, Int32 readBytes, AsyncProtocolRequest asyncRequest)
 at System.Net.Security.SslState.StartReceiveBlob(Byte[] buffer, AsyncProtocolRequest asyncRequest)
 at System.Net.Security.SslState.CheckCompletionBeforeNextReceive(ProtocolToken message, AsyncProtocolRequest asyncRequest)
 at System.Net.Security.SslState.StartSendBlob(Byte[] incoming, Int32 count, AsyncProtocolRequest asyncRequest)
 at System.Net.Security.SslState.ForceAuthentication(Boolean receiveFirst, Byte[] buffer, AsyncProtocolRequest asyncRequest)
 at System.Net.Security.SslState.ProcessAuthentication(LazyAsyncResult lazyResult)
 at System.Net.Security.SslStream.AuthenticateAsClient(String targetHost, X509CertificateCollection clientCertificates, SslProtocols enabledSslProtocols, Boolean checkCertificateRevocation)
 at System.Net.Security.SslStream.AuthenticateAsClient(String targetHost)
 at Microsoft.Exchange.Tools.ExRca.Tests.SSLCertificateTest.PerformTestReally()

Accepted Solution

staub1981 earned 0 total points
ID: 24957364
Finally found a solution for this issue, and as always it was much more simple than I was thinking.

First, I reinstalled the SSL certificate according to Godaddy's instructions.
This solved my SSL problems, but I still wasn't able to complete a sync with a mobile device.  

The solution, was to publish another Exchange Web Client Policy for activesync.
This means there is a policy for both OWA and ActiveSync.  

This ultimately solved the problem I was having.

Author Comment

ID: 24957370
Found My Own Solution

Expert Comment

ID: 24957655

We are having the exact same problem you are having. We have a Godaddy certificate and intermediate certificates. OWA is working perfectly. Autodiscover inside the office seem to work. We are not getting any errors when we run: "Test-OutlookWebServices | fl" in Exchange Management Shell.

We are also getting the handshake error when the SSL certificate is validated at

Could you please provide a little more detailed information of the steps you took to reinstall the certificate or perhaps a link to the instructions. Also the steps required to publish another Exchange Web Client Policy?

Much appreciated.

PS: We can't believe how tricky it has been to get Windows Server 2008 and Exhange 2007 to function as it should. Windows Small Business Server 2003 was so much easier to setup. I don't know what MS is doing in Redmond?! Windows Server 2008 is like Vista - NOT READY!

Expert Comment

ID: 24957662
Please don't close yet. Seeking helpful input from member to resolve autodiscover connectivity issue.

Thank you.

Author Comment

ID: 24957975
First, I'm not an expert... So i don't know if everything I did is necessary to fix it, it just happened  to work for me.

1. First I reinstalled the certificate directly into ISA, rather than exporting the certificate from my exchange server.  I used the same instructions godaddy has for the exchange server.. just used it for the ISA box.

The instructions for doing this is here.

2.  In ISA, I checked the listener to see if I had the correct certificate selected.
I doubled clicked my existing OWA policy, clicked on the listener tab, with my OWA listener selected, I clicked properties, certificates tab, select certificate button, then chose the newly installed certificate, select, ok.

3. In ISA, under the tasks box, click "publish exchange web client access," enter a new policy name, My exchange version was 2007, select exchange activesync, publish to a single site, "use SSL to connect," enter your OWA address, enter your domain name, I used my OWA listener, basic authentication, then finish through.

This is what solved my problem, with a lot of help from Rajith_Enchiparambil's suggestion to use

That site helped direct me to my problems.

Featured Post

Free Tool: Port Scanner

Check which ports are open to the outside world. Helps make sure that your firewall rules are working as intended.

One of a set of tools we are providing to everyone as a way of saying thank you for being a part of the community.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

After hours on line I found a solution which pointed to the inherited Active Directory permissions . You have to give/allow permissions to the "Exchange trusted subsystem" for the user in the Active Directory...
Unified and professional email signatures help maintain a consistent company brand image to the outside world. This article shows how to create an email signature in Exchange Server 2010 using a transport rule and how to overcome native limitations …
In this Micro Video tutorial you will learn the basics about Database Availability Groups and How to configure one using a live Exchange Server Environment. The video tutorial explains the basics of the Exchange server Database Availability grou…
The video tutorial explains the basics of the Exchange server Database Availability groups. The components of this video include: 1. Automatic Failover 2. Failover Clustering 3. Active Manager

728 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question