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Apple Mail setup for Exchange 2010

Posted on 2012-09-04
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Last Modified: 2012-09-11
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
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Question by:Rodrigo Carrilho
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18 Comments
 
LVL 45

Expert Comment

by:Amit
ID: 38363426
Apple Mail uses EWS. Verify EWS settings?
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LVL 13

Expert Comment

by:Xaelian
ID: 38363720
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/
0
 

Author Comment

by:Rodrigo Carrilho
ID: 38363952
Thanks.

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

EWS test results
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LVL 13

Expert Comment

by:Xaelian
ID: 38363981
Autodiscovery is not configured correctly on the MS Exchange Server 2010.
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Author Comment

by:Rodrigo Carrilho
ID: 38363989
Any recommendations at all?
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LVL 45

Expert Comment

by:Amit
ID: 38363999
0
 
LVL 13

Expert Comment

by:Xaelian
ID: 38364004
0
 

Author Comment

by:Rodrigo Carrilho
ID: 38367558
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
0
 
LVL 45

Expert Comment

by:Amit
ID: 38367695
Ya that's right.
0
 
LVL 13

Expert Comment

by:Xaelian
ID: 38367734
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.
0
 

Author Comment

by:Rodrigo Carrilho
ID: 38368110
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
0
 

Author Comment

by:Rodrigo Carrilho
ID: 38372282
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.
0
 

Author Comment

by:Rodrigo Carrilho
ID: 38375440
Apple Mail fails to resolve Exchange autodiscover settings
0
 
LVL 32

Assisted Solution

by:nappy_d
nappy_d earned 750 total points
ID: 38377696
Let's focus on your DNS are you able to resolve your Exchange server from the mac with connectivity issues from your Terminal command line?

If you performed an NSlookup or a dig command and what does it resolve your Exchange your server as?
0
 
LVL 14

Accepted Solution

by:
Kaffiend earned 750 total points
ID: 38378877
Ran into  very same issue with Apple Mail on Mountain Lion.

Only fix in my situation so far has been to add an entry to the MAC's hosts file.  What worked, was to add an entry in the hosts file that points "yourexchangeserver.yourdomain.local" to the server's external IP address   (Big assumption here: your networking is set up in such a way that this IP address is reachable from the inside - you can achieve this through a NAT statement, perhaps).  Try it.

You can read all about this issue in the Apple forums - there's a thread there that's over 30 pages long.  Adding an entry to the hosts file has so far, in our case, been the only workable solution.
0
 

Author Comment

by:Rodrigo Carrilho
ID: 38383609
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.
0
 

Author Comment

by:Rodrigo Carrilho
ID: 38383625
from terminal i did:

nslookup

and it  can resolve

webmail.domain.com
autodiscover.domain.com

both records are pointing to external IP
0
 
LVL 14

Expert Comment

by:Kaffiend
ID: 38384866
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.
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