I am trying to add an Exchange account to Outlook 2010, however I am getting an error message saying the server is unable to connect.

20. September 2013 · Write a comment · Categories: Hotmail, Outlook.com · Tags:
I am trying to add an exchange account to Outlook 2010 through the Auto Account setup tool within Outlook.
It doesn't connect and tells me it will try an un-encrypted connection. After a few minutes, that fails as well giving me the error that the server is unable to connect.

I ran a test on the Microsoft Remote Connectivity Anazlyzer and it is showing me that the autodiscover function is failing. In my DNS records, I have everything that Microsoft is asking of me through Office 365. 
We did just switch servers over, so this may be the issue, but I don't know what steps to take to proceed from here. Can anyone offer any advice?

I appreciate the time.


Below is what the connectivity test showed me:
(I did the Outlook Autodiscover test)

The Microsoft Connectivity Analyzer is attempting to test Autodiscover for *** Email address is removed for privacy ***.
 Testing Autodiscover failed.
 
Test Steps
 
Attempting each method of contacting the Autodiscover service.
 The Autodiscover service couldn't be contacted successfully by any method.
 
Test Steps
 
Attempting to test potential Autodiscover URL https://citymade.com/AutoDiscover/AutoDiscover.xml
 Testing of this potential Autodiscover URL failed.
 
Test Steps
 
Attempting to resolve the host name citymade.com in DNS.
 The host name resolved successfully.
 
Additional Details
 IP addresses returned: 76.74.167.7
Testing TCP port 443 on host citymade.com to ensure it's listening and open.
 The port was opened successfully.
Testing the SSL certificate to make sure it's valid.
 The certificate passed all validation requirements.
 
Test Steps
 
The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server citymade.com on port 443.
 The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
 
Additional Details
 Remote Certificate Subject: CN=www.citymade.com, OU=PositiveSSL, OU="Hosted by Homepage Universe, Inc.", OU=Domain Control Validated, Issuer: CN=PositiveSSL CA, O=Comodo CA Limited, L=Salford, S=Greater Manchester, C=GB.
Validating the certificate name.
 The certificate name was validated successfully.
 
Additional Details
 Host name citymade.com was found in the Certificate Subject Alternative Name entry.
Certificate trust is being validated.
 The certificate is trusted and all certificates are present in the chain.
 
Test Steps
 
The Microsoft Connectivity Analyzer is attempting to build certificate chains for certificate CN=www.citymade.com, OU=PositiveSSL, OU="Hosted by Homepage Universe, Inc.", OU=Domain Control Validated.
 One or more certificate chains were constructed successfully.
 
Additional Details
 A total of 2 chains were built. The highest quality chain ends in root certificate CN=AddTrust External CA Root, OU=AddTrust External TTP Network, O=AddTrust AB, C=SE.
Analyzing the certificate chains for compatibility problems with versions of Windows.
 No Windows compatibility problems were identified.
 
Additional Details
 The certificate chain has been validated up to a trusted root. Root = CN=UTN-USERFirst-Hardware, OU=http://www.usertrust.com, O=The USERTRUST Network, L=Salt Lake City, S=UT, C=US.
Testing the certificate date to confirm the certificate is valid.
 Date validation passed. The certificate hasn't expired.
 
Additional Details
 The certificate is valid. NotBefore = 2/1/2012 12:00:00 AM, NotAfter = 1/31/2014 11:59:59 PM
Checking the IIS configuration for client certificate authentication.
 Client certificate authentication wasn't detected.
 
Additional Details
 Accept/Require Client Certificates isn't configured.
Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
 Autodiscover settings weren't obtained when the Autodiscover POST request was sent.
 
Test Steps
 
The Microsoft Connectivity Analyzer is attempting to retrieve an XML Autodiscover response from URL https://citymade.com/AutoDiscover/AutoDiscover.xml for user *** Email address is removed for privacy ***.
 The Microsoft Connectivity Analyzer failed to obtain an Autodiscover XML response.
 
Additional Details
 A Web exception occurred because an HTTP 404 - NotFound response was received from Unknown.
Headers received:
Connection: close
Content-Length: 7
Content-Type: text/html; charset=iso-8859-1
Date: Fri, 20 Sep 2013 14:40:55 GMT
Server: Apache
Attempting to test potential Autodiscover URL https://autodiscover.citymade.com/AutoDiscover/AutoDiscover.xml
 Testing of this potential Autodiscover URL failed.
 
Test Steps
 
Attempting to resolve the host name autodiscover.citymade.com in DNS.
 The host name resolved successfully.
 
Additional Details
 IP addresses returned: 157.56.244.217, 157.56.234.137, 157.56.236.89, 157.56.240.137
Testing TCP port 443 on host autodiscover.citymade.com to ensure it's listening and open.
 The specified port is either blocked, not listening, or not producing the expected response.
  
 
Additional Details
 A network error occurred while communicating with the remote host.
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 autodiscover.citymade.com in DNS.
 The host name resolved successfully.
 
Additional Details
 IP addresses returned: 157.56.244.217, 157.56.234.137, 157.56.236.89, 157.56.240.137
Testing TCP port 80 on host autodiscover.citymade.com to ensure it's listening and open.
 The port was opened successfully.
The Microsoft Connectivity Analyzer is checking the host autodiscover.citymade.com for an HTTP redirect to the Autodiscover service.
 The redirect (HTTP 301/302) response was received successfully.
 
Additional Details
 Redirect URL: https://autodiscover-s.outlook.com/Autodiscover/Autodiscover.xml
Attempting to test potential Autodiscover URL https://autodiscover-s.outlook.com/Autodiscover/Autodiscover.xml
 Testing of this potential Autodiscover URL failed.
 
Test Steps
 
Attempting to resolve the host name autodiscover-s.outlook.com in DNS.
 The host name resolved successfully.
 
Additional Details
 IP addresses returned: 157.56.241.118, 157.56.240.22, 132.245.2.70, 157.56.240.246, 132.245.1.166, 132.245.1.134, 157.56.232.182, 157.56.237.6, 157.56.236.134, 157.56.245.150
Testing TCP port 443 on host autodiscover-s.outlook.com to ensure it's listening and open.
 The port was opened successfully.
Testing the SSL certificate to make sure it's valid.
 The certificate passed all validation requirements.
 
Test Steps
 
The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server autodiscover-s.outlook.com on port 443.
 The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
 
Additional Details
 Remote Certificate Subject: CN=Outlook.com, OU=MOD, O=Microsoft Corp, L=Redmond, S=washington, C=US, Issuer: CN=VeriSign Class 3 International Server CA - G3, OU=Terms of use at https://www.verisign.com/rpa (c)10, OU=VeriSign Trust Network, O="VeriSign, Inc.", C=US.
Validating the certificate name.
 The certificate name was validated successfully.
 
Additional Details
 Host name autodiscover-s.outlook.com was found in the Certificate Subject Alternative Name entry.
Certificate trust is being validated.
 The certificate is trusted and all certificates are present in the chain.
 
Test Steps
 
The Microsoft Connectivity Analyzer is attempting to build certificate chains for certificate CN=Outlook.com, OU=MOD, O=Microsoft Corp, L=Redmond, S=washington, C=US.
 One or more certificate chains were constructed successfully.
 
Additional Details
 A total of 3 chains were built. The highest quality chain ends in root certificate CN=VeriSign Class 3 Public Primary Certification Authority - G5, OU="(c) 2006 VeriSign, Inc. - For authorized use only", OU=VeriSign Trust Network, O="VeriSign, Inc.", C=US.
Analyzing the certificate chains for compatibility problems with versions of Windows.
 No Windows compatibility problems were identified.
 
Additional Details
 The certificate chain has been validated up to a trusted root. Root = OU=Class 3 Public Primary Certification Authority, O="VeriSign, Inc.", C=US.
Testing the certificate date to confirm the certificate is valid.
 Date validation passed. The certificate hasn't expired.
 
Additional Details
 The certificate is valid. NotBefore = 4/4/2013 12:00:00 AM, NotAfter = 4/5/2014 11:59:59 PM
Checking the IIS configuration for client certificate authentication.
 Client certificate authentication wasn't detected.
 
Additional Details
 Accept/Require Client Certificates isn't configured.
Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
 Autodiscover settings weren't obtained when the Autodiscover POST request was sent.
 
Test Steps
 
The Microsoft Connectivity Analyzer is attempting to retrieve an XML Autodiscover response from URL https://autodiscover-s.outlook.com/Autodiscover/Autodiscover.xml for user *** Email address is removed for privacy ***.
 The Microsoft Connectivity Analyzer failed to obtain an Autodiscover XML response.
 
Additional Details
 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:
RequestId: 022f7c63-f18a-49c7-bb7a-c07c9161b50d
X-DiagInfo: BY2PRD0811CA015
Content-Length: 0
Cache-Control: private
Date: Fri, 20 Sep 2013 14:42:56 GMT
Server: Microsoft-IIS/7.5
WWW-Authenticate: Basic Realm=""
X-AspNet-Version: 2.0.50727
X-Powered-By: ASP.NET

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