Hi

I have fresh Exchange 2013 server sits on Windows 2012R2 and all servers and Windows 2012R2.

1 AD server domain name is testing.local

1 MBX Server Exchange 2013

2 CAS Server Exchange 2013

Have enabled POP3, SMTP, WEB and outlook anywhere with ucc certificate and assigned to iis and smtp. 

The actual domain name is testing.local and hosted mail tenant domain name is asteriks.com. 

Have created autodiscover.asteriks.com and internally it works fine. While coming to external url the outlook anywhere client gets prompted for credential again and again. We tried NTLM and BASIC authentication but it didn't work.

https://mail.asteriks.com/rpc/rpcproxy.dll

https://autodiscover.asteriks.com/AutoDiscover/AutoDiscover.xml 

works internally and externally.

When i tried autodiscover check i got this error.

An HTTP 401 Unauthorized response was received from the remote Unknown server. This is usually the result of an incorrect username or password. If you are attempting to log onto an Office 365 service, ensure you are using your full User Principal Name (UPN).
Headers received:
request-id: 7cf9345a-00c0-414f-9cdc-a084ee93d185
Server: Microsoft-IIS/8.0
WWW-Authenticate: Digest qop="auth",algorithm=MD5-sess,nonce="+Upgraded+v1fd4345daa84053bce7befa284f11356f669fe0f35259cf013209b85d24ce3fddd40246fc915972bc3b2493fdddf3342f9839deecf8400dba",charset=utf-8,realm="Digest",Basic realm="asteriks.com"
X-Powered-By: ASP.NET
X-FEServer: cas02
Date: Wed, 15 Apr 2014 09:05:03 GMT
Content-Length: 0

HTTP Response Headers:
request-id: 7cf9345a-00c0-414f-9cdc-a084ee93d185
Server: Microsoft-IIS/8.0
WWW-Authenticate: Digest qop="auth",algorithm=MD5-sess,nonce="+Upgraded+v1fd4345daa84053bce7befa284f11356f669fe0f35259cf013209b85d24ce3fddd40246fc915972bc3b2493fdddf3342f9839deecf8400dba",charset=utf-8,realm="Digest",Basic realm="asteriks.com"
X-Powered-By: ASP.NET
X-FEServer: CAS02
Date: Wed, 15 Apr 2014 09:05:03 GMT
Content-Length: 0

Elapsed Time: 1399 ms.

Outlook RPC connectivity test resulted the following error.

An HTTP 401 Unauthorized response was received from the remote Unknown server. This is usually the result of an incorrect username or password. If you are attempting to log onto an Office 365 service, ensure you are using your full User Principal Name (UPN).
Headers received:
request-id: 12bb2e70-d886-403e-8316-bf98a98505a7
Server: Microsoft-IIS/8.0
WWW-Authenticate: Digest qop="auth",algorithm=MD5-sess,nonce="+Upgraded+v1c4d07043428128f0743ee319fef773bd75b62ea55359cf01bfb03946baac3c952936b15ac4af19f98e850409314c70b885c5ac265395ef41",charset=utf-8,realm="Digest",Basic realm="autodiscover.asteriks.com"
X-Powered-By: ASP.NET
X-FEServer: cas02
Date: Wed, 15 Apr 2014 09:10:00 GMT
Content-Length: 0


HTTP Response Headers:
request-id: 12bb2e70-d886-403e-8316-bf98a98505a7
Server: Microsoft-IIS/8.0
WWW-Authenticate: Digest qop="auth",algorithm=MD5-sess,nonce="+Upgraded+v1c4d07043428128f0743ee319fef773bd75b62ea55359cf01bfb03946baac3c952936b15ac4af19f98e850409314c70b885c5ac265395ef41",charset=utf-8,realm="Digest",Basic realm="autodiscover.asteriks.com"
X-Powered-By: ASP.NET
X-FEServer: cas02
Date: Wed, 15 Apr 2014 09:10:00 GMT
Content-Length: 0

Elapsed Time: 1399 ms.

Please help how to resolve this issue, our goal is to enable outlook anywhere.

Are you running SP1?  That is required for Exchange 2013 to run on Windows Server 2012 R2.

Exchange 2013 doesn't have sp1. Also the issue is resolved. Thanks!

Good Morning

Please try testconnectivity  for ActiveSync. 

But I think your problem is that you need to set up Inherance in the users that you want to use activesync.

Please check the autodiscover externally using: https://testconnectivity.microsoft.com/

Then search for the yellow and red errors.

Remember that the Certificate in the IIS using for the 2 CAS and for MBX have to be the same.

I mean Check the binding in CAS (it should be in * 443). and in the MBX it should be in the ( * 444 port).

I will start this way.

Check internal and external access

get-AutodiscoverVirtualDirectory   |fl
get-ClientAccessServer             |fl
get-webservicesvirtualdirectory    |fl
get-oabvirtualdirectory            |fl
get-owavirtualdirectory            |fl
get-ecpvirtualdirectory            |fl
get-ActiveSyncVirtualDirectory     |fl

And this should set external:

$baseurl="https://mail.asteriks.com/"
$serverFQN="mail.asteriks.local"
$server="mail"
#Set-ClientAccessServer -Identity $serverName -AutodiscoverServiceInternalUri "$baseurl/autodiscover/autodiscover.xml"
set-OwaVirtualDirectory -identity "$mail\owa (default Web site)" -ExternalUrl "$baseurl/owa"
set-OabVirtualDirectory "OAB (Default Web Site)" -ExternalUrl "$baseurl/oab" 
set-AutodiscoverVirtualDirectory -Identity "'$mail\Autodiscover (Default Web Site)" -ExternalUrl "baseurl/autodiscover" 
Set-WebServicesVirtualDirectory -Identity "$mail\EWS (Default Web Site)" -ExternalUrl "$baseurl/ews/exchange.asmx"
set-ecpVirtualDirectory -Identity "$mail\ecp (Default Web Site)" -ExternalUrl ""$baseurl/ecp" 
set-ActiveSyncVirtualDirectory  -identity "Microsoft-Server-ActiveSync (Default Web Site)" -ExternalUrl "$baseurl/Microsoft-Server-ActiveSync"

• Edited by j0rt3g4 6 hours 2 minutes ago