Hi guys,

Currently I'm having an issue in creating mailboxes within Outlook. As stated in the subject all steps verifies until it gets to the point of "logging on to the mail server"

For testing purposes I use the Auto Account setup, not specifying the exchange server FQDN and outlook anywhere details. Prior to the issue I'm experiencing now it did work through this method.

During the auto account setup it successfully verifies the following: Establishing network connection, searching for the email address settings ( where it prompts authentication, once given resolves successfully ), and finally at the last step of "logging on to the mail server" it prompts authentication once again, after given once more, it fails, stating Exchange should be online or connected.

This is a new installation of Exchange 2013 Std on a small scale for 10-20 users. Installed as a stand-alone server.

All mailboxes are accessible through OWA, just setting up from within Outlook where the issue is encountered.

I've successfully queried the autodiscover service which resolves to the correct address as well as the FQDN for external use ( as for OWA ).

What am I missing here, can it be certification issue? I'm currently using the self-signed certificates exchange generated by default during installation, as I'm waiting on the releasing of a 3rd party SSL cert. Creating these mailboxes in Outlook did work previously, also only relying on the self-signed certs.

Any advise would be appreciated.

Regards

• Edited by Techn101 21 hours 26 minutes ago

Hi,

there are several things you can try:

1) When you are beeing asked for credentials (again and again), do you enter domain\username and password? Did you try to remove cached credential in user's profile properties? (search "manage windows credentials" in Control panel)

2) Have you tried Remote connectivity analyzer? https://testconnectivity.microsoft.com

3) You can also enable Outlook debug logging. But from my point of view it is authentication issue.

Good luck

You have to verify your Cluster model and do remote analyzer..

Hi there

1) As you've mentioned the authentication I use is domain\username and password. I also cleared all cached credentials and tried again with no avail.

2) Here are the results for the remote connectivity analyser:

The Microsoft Connectivity Analyzer is attempting to test Autodiscover for "email address".
 Testing Autodiscover failed.
 
Additional Details
 
Elapsed Time: 3947 ms.

 
Test Steps
 
Attempting each method of contacting the Autodiscover service.
 The Autodiscover service couldn't be contacted successfully by any method.
 
Additional Details
 
Elapsed Time: 3947 ms.

 
Test Steps
 
Attempting to test potential Autodiscover URL https
 Testing of this potential Autodiscover URL failed.
 
Additional Details
 
Elapsed Time: 1492 ms.

 
Test Steps
 
Attempting to resolve the host name domain.com in DNS.
 The host name resolved successfully.
 
Additional Details
 
IP addresses returned: xxx.xxx.xx.xxx

Elapsed Time: 227 ms.

Testing TCP port 443 on host domain.com to ensure it's listening and open.
 The port was opened successfully.
 
Additional Details
 
Elapsed Time: 378 ms.

Testing the SSL certificate to make sure it's valid.
 The SSL certificate failed one or more certificate validation checks.
 
Additional Details
 
Elapsed Time: 885 ms.

 
Test Steps
 
The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server domain.com on port 443.
 The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
 
Additional Details
 
Remote Certificate Subject: OU=Domain Control Validated - RapidSSL(R), OU=See, OU=GT14623739, SERIALNUMBER=XLjzfa7swZZElnkDNb4XkkTNhKV6F1a9, Issuer: CN=RapidSSL CA, O="GeoTrust, Inc.", C=US.

Elapsed Time: 861 ms.

Validating the certificate name.
 Certificate name validation failed.
  Tell me more about this issue and how to resolve it
 
Additional Details
 
Host name domain.com doesn't match any name found on the server certificate - RapidSSL(R), OU=See  (c)12, OU=GT14623739, SERIALNUMBER=XLjzfa7swZZElnkDNb4XkkTNhKV6F1a9.

Elapsed Time: 0 ms.

Attempting to test potential Autodiscover URL autodiscoverdomaincom443/Autodiscover/Autodiscover
 Testing of this potential Autodiscover URL failed.
 
Additional Details
 
Elapsed Time: 1486 ms.

 
Test Steps
 
Attempting to resolve the host name autodiscover.domain.com in DNS.
 The host name resolved successfully.
 
Additional Details
 
IP addresses returned: xxx.xxx.xx.xxx

Elapsed Time: 289 ms.

Testing TCP port 443 on host autodiscover.domain.com to ensure it's listening and open.
 The port was opened successfully.
 
Additional Details
 
Elapsed Time: 336 ms.

Testing the SSL certificate to make sure it's valid.
 The SSL certificate failed one or more certificate validation checks.
 
Additional Details
 
Elapsed Time: 859 ms.

 
Test Steps
 
The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server autodiscover.domain.com on port 443.
 The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
 
Additional Details
 
Remote Certificate Subject: CN=HOST, Issuer: CN=HOST.

Elapsed Time: 836 ms.

Validating the certificate name.
 Certificate name validation failed.
  Tell me more about this issue and how to resolve it
 
Additional Details
 
Host name autodiscover.domain.com doesn't match any name found on the server certificate CN=HOST.

Elapsed Time: 0 ms.

Attempting to contact the Autodiscover service using the HTTP redirect method.
 The attempt to contact Autodiscover using the HTTP Redirect method failed.
 
Additional Details
 
Elapsed Time: 833 ms.

 
Test Steps
 
Attempting to resolve the host name autodiscover.domain.com in DNS.
 The host name resolved successfully.
 
Additional Details
 
IP addresses returned: xxx.xxx.xx.xxx

Elapsed Time: 7 ms.

Testing TCP port 80 on host autodiscover.domain.com to ensure it's listening and open.
 The port was opened successfully.
 
Additional Details
 
Elapsed Time: 281 ms.

The Microsoft Connectivity Analyzer is checking the host autodiscover.domain.com for an HTTP redirect to the Autodiscover service.
 The Microsoft Connectivity Analyzer failed to get an HTTP redirect response for Autodiscover.
 
Additional Details
 
An HTTP 403 forbidden response was received. The response appears to have come from Unknown. Body of the response:
HTTP Response Headers:
X-FEServer: HOST
Content-Length: 0
Date: Thu, 25 Jun 2015 11:28:21 GMT
Server: Microsoft-IIS/8.5
X-Powered-By: ASP.NET

Elapsed Time: 544 ms.

Attempting to contact the Autodiscover service using the DNS SRV redirect method.
 The Microsoft Connectivity Analyzer failed to contact the Autodiscover service using the DNS SRV redirect method.
 
Additional Details
 
Elapsed Time: 80 ms.

 
Test Steps
 
Attempting to locate SRV record _autodiscover._tcp.domain.com in DNS.
 The Autodiscover SRV record wasn't found in DNS.
  Tell me more about this issue and how to resolve it
 
Additional Details
 
Elapsed Time: 80 ms.

I'm sure the results of this points clearly to a few things that might be the root of the problem, certificate and autodiscover?

Is autodiscover external URL covered by certificate you use for II

As I can see from the default self signed cert, no.

Can a new self signed cert be issued containing the autodisover URL?

Yes. Anyway best practise is using "more trusted" certificate - a commercial or at least a domain one. Self signed is good for testing. When you re-run remote connectivity analyzer, check the checkbox ignore certificate trust.