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Apple Mail setup for Exchange 2010

Hi There,

I am trying to setup an Exchange mail account on Apple Mail version 6 and OSX 10.8.1.

After adding a new account entering the name, email and password details Apple Mail tries do resolve the settings but if fails with the following error message.

The Exchange server “servername.domain.local” is not responding. Try checking the network connection, and that the server name is correct. Otherwise, the server might be temporarily unavailable. If you continue, you might not be able to receive messages.

If I try using MS Outlook 2010 if works fine.
The server is a Exchange 2010 SP2 running os a Win 2K8 R2 SP1.

Any suggestions would be appreciated.

Thanks,
Rod

Amit

Apple Mail uses EWS. Verify EWS settings?

Xaelian

This tutorial to connect to Apple Mail is the same for Mountain Lion.
http://www.techrepublic.com/blog/mac/how-to-connect-lion-to-exchange-servers/1527

But like amitkulshrestha said EWS needs to be enabled on the Exchange server. Mail uses this to retreive anything.

You can use the following webpage to test the EWS settings of the Exchange server:
https://www.testexchangeconnectivity.com/

Rodrigo Carrilho

ASKER

Thanks.

I run the test and attached here. Is it easy to understand what seems to be the problem?

Xaelian

Autodiscovery is not configured correctly on the MS Exchange Server 2010.

Rodrigo Carrilho

ASKER

Any recommendations at all?

Amit

Check this
http://premnair.wordpress.com/2010/07/03/configure-ews-autodiscover-owa-oab-ecp-on-exchange-server-2010/

Xaelian

you can do the following:

http://www.msexchange.org/articles_tutorials/exchange-server-2010/management-administration/exchange-autodiscover.html

Or the technet post for the Exchange Services for autodiscovery service:
http://technet.microsoft.com/en-us/library/bb201695.aspx

Rodrigo Carrilho

ASKER

thank you for the articles. I read all of them, it's a bit more clear now... I hope.

I run the following command using the Shell
get-webservicesvirtualdirectory | fl

and the results are pasted below:

RunspaceId : 80a56064-e498-4305-8835-1da857d25c2a
CertificateAuthentication :
InternalNLBBypassUrl : https://servername.domain.local/ews/exchange.asmx
GzipLevel : High
MRSProxyEnabled : False
MRSProxyMaxConnections : 100
Name : EWS (Default Web Site)
InternalAuthenticationMethods : {Ntlm, WindowsIntegrated, WSSecurity}
ExternalAuthenticationMethods : {Ntlm, WindowsIntegrated, WSSecurity}
LiveIdSpNegoAuthentication : False
WSSecurityAuthentication : True
LiveIdBasicAuthentication : False
BasicAuthentication : False
DigestAuthentication : False
WindowsAuthentication : True
MetabasePath : IIS://servername.domain.local /W3SVC/1/ROOT/EWS
Path : D:\Program Files\Exchange\ClientAccess\exchweb\EWS
ExtendedProtectionTokenChecking : None
ExtendedProtectionFlags : {}
ExtendedProtectionSPNList : {}
Server : servername
InternalUrl : https:// servername.domain.local /EWS/Exchange.asmx
ExternalUrl : https://domain.com/ews/exchange.asmx
AdminDisplayName :
ExchangeVersion : 0.10 (14.0.100.0)
DistinguishedName : CN=EWS (Default Web Site),CN=HTTP,CN=Protocols,CN=SERVERNAME,CN=Servers,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=Company Name,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=domain,DC=Local
Identity : servername\EWS (Default Web Site)
Guid : 6ab6c9d0-ab3d-48de-a916-b3714f46af1a
ObjectCategory : domain.Local/Configuration/Schema/ms-Exch-Web-Services-Virtual-Directory
ObjectClass : {top, msExchVirtualDirectory, msExchWebServicesVirtualDirectory}
WhenChanged : 5/28/2012 4:35:36 PM
WhenCreated : 5/28/2012 4:35:34 PM
WhenChangedUTC : 5/28/2012 3:35:36 PM
WhenCreatedUTC : 5/28/2012 3:35:34 PM
OrganizationId :
OriginatingServer : servername.domain.local
IsValid : True

Am I right to say the problem here is the external URL fro EWS? Therefore I shall run

Set-WebServicesVirtualDirectory -identity "servername\EWS (Default Web Site)" -externalurl https://webmail.domain.com/EWS/Exchange.asmx -BasicAuthentication:$True

We have 3rd party UCC/SLL certificate with the followings SAN included

webmail.domain.com
servername.domain.local
autodiscover.domain.com
autodiscover.domain.local
domain.com

Thanks again,
Rod

Amit

Ya that's right.

Xaelian

If you're not sure if you need to run that command. Try the connection again or check with the page I gave you.

It can be that you've configured the autodiscovery correctly but that you're missing something else now. With the report of the tool, you'll see what is correct :).

What I see is that you're correct that you need to execute that command. But to be sure run the page again. If everything has a green OK button before it, everything is correct.

Rodrigo Carrilho

ASKER

thanks.

I run the command

Set-WebServicesVirtualDirectory -identity "servername\EWS (Default Web Site)" -externalurl https://webmail.domain.com/EWS/Exchange.asmx -BasicAuthentication:$True

waited 30 min, checked event viewer and I can see The Exchange Web Services started successfully.

Run https://www.testexchangeconnectivity.com/ again and I still faills.

Also I run the comand below to check Autodiscovery settings.

get-autodiscovervirtualdirectory | fl *url*

InternalUrl :
ExternalUrl :

(both URL are come out blank)
Can I fix this Autodiscovery using one of the commands below?

Set-ClientAccessServer -Identity servername -AutoDiscoverServiceExternalUri https://webmail.domain.com/Autodiscover/Autodiscover.xml

or

Set-ClientAccessServer -Identity servername -AutoDiscoverServiceExternalUri https://autodiscover.domain.com/Autodiscover/Autodiscover.xml

Thanks,
Rod

Rodrigo Carrilho

ASKER

Hi Again,

From EMC, I have reseted client access virtual directories for:

OWA
ECP
ActiveSync

followed by IISreset /noforce

now external URLs are:

OWA: https://webmail.domain.com/owa
ECP: https://webmail.domain.com/ecp
OAB: https://webmail.domain.com/oab

ActiveSync: I receive an error when right click and properties

"The properties on this object have invalid data. If you click OK, default values will be used instead and will be saved if you do not change them before hitting Apply or OK on the property page. If you click cancel, the object will be displayed read-only and corrupted values will be retained.

running Get-ClientAccessServer SERVER | fl from Shell

I can see the Autodiscover URL as: https://domain.com/autodiscover/autodiscover.xml

and finally by running https://www.testexchangeconnectivity.com unfortunately it fails again....

Attempting to test potential Autodiscover URL https://domain.com/AutoDiscover/AutoDiscover.xml

So.... the Autodiscover URL from shell is the same from https://www.testexchangeconnectivity.com report. So what I am missing now? I

Thanks.

Rodrigo Carrilho

ASKER

SOLUTION

Irwin W.

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Kaffiend

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Rodrigo Carrilho

ASKER

I added "yourexchangeserver.yourdomain.local" and pointed to external IP address (hosts file)
From network utility I can ping successfully on "yourexchangeserver.yourdomain.local"

Apple still keeps searching for yourexchangeserver.yourdomain.local until times out.

I installed Outlook 2011 for Mac on the same machine and it work's like a charm.

Rodrigo Carrilho

ASKER

from terminal i did:

nslookup

and it can resolve

webmail.domain.com
autodiscover.domain.com

both records are pointing to external IP

Kaffiend

In Apple networking, nslookup does not use the same mechanism as dns name lookups (I know, sounds counterintuitive, but to my knowledge, true)

If you added that entry to the hosts file, and it still doesn't work, try to flush the dnscache.