Issue with Mac mail and external outlook users not connecting to exchange

Posted on 2013-01-13
Last Modified: 2013-01-28
Hi All,

We currently have an issue with exchange in both our internal/ external Mac users cannot connect to exchange and only external MS outlook users cannot connect.

All smart phone devices (i.e. iPhone, Android etc..) which are outside our domain network i.e. using a Mobile data connection can still connect and send and receive mail and all internal outlook users can connect + send/receive mail fine as well.

I have checked all obvious things such as the MS Exchange services and ensured they are all running, rebooted the Exchange server and also checked bindings within IIS and from what I can tell they appear to be OK.

I am now stuck on this and I can't see how it would be a network issue as mentioned above the smart phones (which are outside the network) are connecting and puling down the mail just fine. I am thinking its perhaps related to an active syc issue, but im am by far no exchange expert and urgently need the help and advise of a EE exchange guru to assit with this.

Thanks in advance,
Question by:Adma1
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Author Comment

ID: 38773011
I should also add the OWA is working fine and can be accessed outside the network.

Author Comment

ID: 38773072
I have performed auto discovery test using

See results below.

      Attempting the Autodiscover and Exchange ActiveSync test (if requested).
       Testing of Autodiscover for Exchange ActiveSync failed.
      Test Steps
      Attempting each method of contacting the Autodiscover service.
       The Autodiscover service couldn't be contacted successfully by any method.
      Test Steps note company name has been substituted with the word "company"
      Attempting to test potential Autodiscover URL
       Testing of this potential Autodiscover URL failed.
      Test Steps
      Attempting to test potential Autodiscover URL
       Testing of this potential Autodiscover URL failed.
      Test Steps
      Attempting to contact the Autodiscover service using the HTTP redirect method.
       The attempt to contact Autodiscover using the HTTP Redirect method failed.
      Test Steps
      Attempting to resolve the host name in DNS.
       The host name resolved successfully.
      Additional Details
      Testing TCP port 80 on host to ensure it's listening and open.
       The port was opened successfully.
      ExRCA is checking the host for an HTTP redirect to the Autodiscover service.
       ExRCA failed to get an HTTP redirect response for Autodiscover.
      Additional Details
      Attempting to contact the Autodiscover service using the DNS SRV redirect method.
       ExRCA failed to contact the Autodiscover service using the DNS SRV redirect method.
      Test Steps
      Attempting to locate SRV record in DNS.
       The Autodiscover SRV record wasn't found in DNS.

Author Comment

ID: 38773078
I also came ascross a forum suggestion to check the following:

On Exchange CAS server, open IIS console,
Go to default web site, double click “SSL Settings”,  make sure Client Certificates is set to “Ignore”
Click Autodiscover, double click “SSL Settings”,  make sure Client Certificates is set to “Ignore”
Click EWS, double click “SSL Settings”,  make sure Client Certificates is set to “Ignore”
Click OAB, double click “SSL Settings”,  make sure Client Certificates is set to “Ignore”
Please run IISRESET command to load the changes.

i have checked each of these and can confirm our configuration is identical to the suggestion above.
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LVL 19

Expert Comment

ID: 38773603
If you are using Exchange 2007 and above and the mac user using entourage or Outlook for mac, please make sure you run update for both mac client. I had experianced for mac user unable to connect to exchange server when we did upgrade our Exchange 2007 few years back. After did some googling, we did update the mac client then mac user able to send/receive mail (internal/external)

It appeared to me that you have issue with SRV record:

Attempting to locate SRV record in DNS.
       The Autodiscover SRV record wasn't found in DNS.

Look at this link:, do it on your public DNS

Then run the test again.

Author Comment

ID: 38773900
Hi thanks for the response,

The issue affects all Mac users and we only use the.native Mac mail client within snow leopard and our external users using outlook.

Its strange how this issue jut came about and nothing had changed in order to trigger the issue to occur.

Author Comment

ID: 38773904
Also I read on forum I came across that the issue could be related to the exchange server not being able to identify the name on the certificate, but this has not changed and the certificate has not expired.

Accepted Solution

Adma1 earned 0 total points
ID: 38812641
Hi all,

After a pain staking attempt to resolve this I found that the issue was in fact related to a .Net update, applying the following update resolved this issue.

Thanks for all the assistance with this issue to date.

Author Closing Comment

ID: 38826205
Hot fix update resolved the issue and exchange now connects as required.

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