I am having problem connecting to our Exchange 2013 from Outlook 2016 application running on external PC (outside LAN) or internal PC but not joined to Domain using auto-discovery. However there is no issue connecting to Exchange from Domain joined PC, auto-discovery working fine and connects to Exchange.The problem is, when I try to setup Exchange profile by entering name, email address and password, it tries to find Exchange server through auto-discovery and after few seconds it prompts for entering password where my email-address is shown as user-name. Even after I put my password correctly, it still opens-up the same password prompt window. It keeps on coming again and again, no matter how many times I put my correct password.Sometime, though, it throws another message "An encrypted connection to your mail server is not available. Click next to attempt using an unencrypted connection.". Then selecting unencrypted connection, eventually it fails and give me option to choose Activesync or IMAP/POP3.From Domain-joined PC and when logged-into Domain,
Auto-discovery seems working fine because
Outlook 2016 can find the Exchange and able to create profile and connect to server without any issue. It does not prompt for any password since I am already logged-into domain. Also from Smart-phones, Outlook or other Email clients can be setup to connect to Exchange and no issue with that. Only with computers which are not on domain. Not sure what is causing this.
I tried using Activesync, but got to know its for lite-version of email clients and not for full-featured client which Outlook is.My guess, the issue is lying somewhere in Exchange configuration the way authentication is being handled for outside domain. I don't think its an issue with Outlook application, I have tried it on different PCs with 2016 and 2013 version of Outlook, same result.I have had lots of time spent to troubleshoot this issue, no luck ye. I will appreciate any advice which may help to resolve the issue.
*****************************Outlook Connectivity Test Start*************** Testing Outlook connectivity. The Outlook connectivity test failed. Additional Details Elapsed Time: 12533 ms. Test Steps
The Microsoft Connectivity Analyzer is attempting to test Autodiscover for user.name@mybiz.com. Testing Autodiscover failed. Additional Details Elapsed Time: 12533 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: 12533 ms. Test Steps
Attempting to test potential Autodiscover URL https: //mybiz.com:443/Autodiscover/Autodiscover.xml Testing of this potential Autodiscover URL failed. Additional Details Elapsed Time: 953 ms. Test Steps
Attempting to resolve the host name mybiz.com in DNS. The host name couldn't be resolved. Tell me more about this issue and how to resolve it Additional Details Host mybiz.com couldn't be resolved in DNS InfoNoRecords. Elapsed Time: 953 ms.
Attempting to test potential Autodiscover URL https: //autodiscover.mybiz.com:443/Autodiscover/Autodiscover.xml Testing of this potential Autodiscover URL failed. Additional Details Elapsed Time: 10995 ms. Test Steps
Attempting to resolve the host name autodiscover.mybiz.com in DNS. The host name resolved successfully. Additional Details IP addresses returned: 132.245.254.88, 132.245.43.120, 40.100.29.216, 132.245.69.40, 40.100.0.200, 40.100.16.24, 40.96.2.136, 40.100.20.8, 40.100.17.24, 40.100.54.200, 2a01:111:f400:5239::8, 2603:1046:3:15::8, 2a01:111:f400:b428::8, 2a01:111:f400:a428::8, 2603:1046:800:1::8, 2a01:111:f400:2e01::8, 2603:1046:805::8, 2603:1046:202:14::8, 2603:1046:804:1::8, 2a01:111:f400:2f4a::8 Elapsed Time: 9 ms.
Testing TCP port 443 on host autodiscover.mybiz.com to ensure it's listening and open. The specified port is either blocked, not listening, or not producing the expected response. Tell me more about this issue and how to resolve it Additional Details A network error occurred while communicating with the remote host. Elapsed Time: 10985 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: 498 ms. Test Steps
Attempting to resolve the host name autodiscover.mybiz.com in DNS. The host name resolved successfully. Additional Details IP addresses returned: 132.245.254.88, 132.245.43.120, 40.100.29.216, 132.245.69.40, 40.100.0.200, 40.100.16.24, 40.96.2.136, 40.100.20.8, 40.100.17.24, 40.100.54.200, 2a01:111:f400:5239::8, 2603:1046:3:15::8, 2a01:111:f400:b428::8, 2a01:111:f400:a428::8, 2603:1046:800:1::8, 2a01:111:f400:2e01::8, 2603:1046:805::8, 2603:1046:202:14::8, 2603:1046:804:1::8, 2a01:111:f400:2f4a::8 Elapsed Time: 7 ms.
Testing TCP port 80 on host autodiscover.mybiz.com to ensure it's listening and open. The port was opened successfully. Additional Details Elapsed Time: 47 ms.
The Microsoft Connectivity Analyzer is checking the host autodiscover.mybiz.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 HTTP Response Headers: Pragma: no-cache X-FEServer: HK2PR0201CA0013,HK2PR0201CA0013 X-RequestId: 9764b2ca-bd2a-4598-b9fa-731b64c620d8 Connection: close Content-Length: 0 Cache-Control: no-cache Date: Thu, 12 Jan 2017 09:50:19 GMT Location: https: //autodiscover-s.outlook.com/Autodiscover/Autodiscover.xml Server: Microsoft-IIS/8.5 X-Powered-By: ASP.NET Elapsed Time: 74 ms.
Attempting to test potential Autodiscover URL https:// autodiscover-s.outlook.com/Autodiscover/Autodiscover.xml Testing of this potential Autodiscover URL failed. Additional Details Elapsed Time: 366 ms. Test Steps
Attempting to resolve the host name autodiscover-s.outlook.com in DNS. The host name resolved successfully. Additional Details IP addresses returned: 132.245.41.98, 40.100.29.34, 40.96.47.34, 40.100.1.146, 132.245.254.226, 132.245.254.98, 132.245.254.130, 40.96.1.194, 40.100.1.162, 40.100.16.2, 2603:1046:202:14::2, 2a01:111:f400:2f4a::2, 2a01:111:f400:5239::2, 2603:1046:3:15::2, 2a01:111:f400:b428::2, 2a01:111:f400:a428::2, 2603:1046:800:1::2, 2a01:111:f400:2e01::2, 2603:1046:805::2, 2603:1046:804:1::2 Elapsed Time: 20 ms.
Testing TCP port 443 on host autodiscover-s.outlook.com to ensure it's listening and open. The port was opened successfully. Additional Details Elapsed Time: 56 ms.
Testing the SSL certificate to make sure it's valid. The certificate passed all validation requirements. Additional Details Elapsed Time: 106 ms. 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=Microsoft Corporation, O=Microsoft Corporation, L=Redmond, S=WA, C=US, Issuer: CN=Microsoft IT SSL SHA2, OU=Microsoft IT, O=Microsoft Corporation, L=Redmond, S=Washington, C=US. Elapsed Time: 63 ms.
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. Elapsed Time: 1 ms.
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=Microsoft Corporation, O=Microsoft Corporation, L=Redmond, S=WA, C=US. 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=Baltimore CyberTrust Root, OU=CyberTrust, O=Baltimore, C=IE. Elapsed Time: 13 ms.
Analyzing the certificate chains for compatibility problems with versions of Windows. Potential compatibility problems were identified with some versions of Windows. Additional Details The Microsoft Connectivity Analyzer can only validate the certificate chain using the Root Certificate Update functionality from Windows Update. Your certificate may not be trusted on Windows if the "Update Root Certificates" feature isn't enabled. Elapsed Time: 3 ms.
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 = 10/13/2015 10:20:04 PM, NotAfter = 10/12/2017 10:20:04 PM Elapsed Time: 0 ms.
Checking the IIS configuration for client certificate authentication. Client certificate authentication wasn't detected. Additional Details Accept/Require Client Certificates isn't configured. Elapsed Time: 80 ms.
Attempting to send an Autodiscover POST request to potential Autodiscover URLs. Autodiscover settings weren't obtained when the Autodiscover POST request was sent. Additional Details Elapsed Time: 102 ms. 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 user.name@mybiz.com. 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). HTTP Response Headers: request-id: 3659bdac-42e6-4b72-a9e3-a4536203df80 X-CasErrorCode: UnauthenticatedRequest X-FEServer: KL1PR02CA0010 Content-Length: 0 Cache-Control: private Date: Thu, 12 Jan 2017 09:50:19 GMT Server: Microsoft-IIS/8.5 WWW-Authenticate: Basic Realm="" X-AspNet-Version: 4.0.30319 X-Powered-By: ASP.NET Elapsed Time: 101 ms. *******************Outlook Connectivity Test End**************************
******************Outlook Autodiscovery Test Start************************
The Microsoft Connectivity Analyzer is attempting to test Autodiscover for user.name@mybiz.com. Testing Autodiscover failed. Additional Details Elapsed Time: 12955 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: 12955 ms. Test Steps
Attempting to test potential Autodiscover URL https: //mybiz.com:443/Autodiscover/Autodiscover.xml Testing of this potential Autodiscover URL failed. Additional Details Elapsed Time: 379 ms. Test Steps
Attempting to resolve the host name mybiz.com in DNS. The host name couldn't be resolved. Tell me more about this issue and how to resolve it Additional Details Host mybiz.com couldn't be resolved in DNS InfoNoRecords. Elapsed Time: 379 ms.
Attempting to test potential Autodiscover URL https: //autodiscover.mybiz.com:443/Autodiscover/Autodiscover.xml Testing of this potential Autodiscover URL failed. Additional Details Elapsed Time: 11552 ms. Test Steps
Attempting to resolve the host name autodiscover.mybiz.com in DNS. The host name resolved successfully. Additional Details IP addresses returned: 40.100.0.200, 40.100.16.24, 40.96.2.136, 40.100.20.8, 40.100.17.24, 40.100.54.200, 132.245.254.88, 132.245.43.120, 40.100.29.216, 132.245.69.40, 2603:1046:3:15::8, 2a01:111:f400:b428::8, 2a01:111:f400:a428::8, 2603:1046:800:1::8, 2a01:111:f400:2e01::8, 2603:1046:805::8, 2603:1046:202:14::8, 2603:1046:804:1::8, 2a01:111:f400:2f4a::8, 2a01:111:f400:5239::8 Elapsed Time: 326 ms.
Testing TCP port 443 on host autodiscover.mybiz.com to ensure it's listening and open. The specified port is either blocked, not listening, or not producing the expected response. Tell me more about this issue and how to resolve it Additional Details A network error occurred while communicating with the remote host. Elapsed Time: 11226 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: 390 ms. Test Steps
Attempting to resolve the host name autodiscover.mybiz.com in DNS. The host name resolved successfully. Additional Details IP addresses returned: 40.100.0.200, 40.100.16.24, 40.96.2.136, 40.100.20.8, 40.100.17.24, 40.100.54.200, 132.245.254.88, 132.245.43.120, 40.100.29.216, 132.245.69.40, 2603:1046:3:15::8, 2a01:111:f400:b428::8, 2a01:111:f400:a428::8, 2603:1046:800:1::8, 2a01:111:f400:2e01::8, 2603:1046:805::8, 2603:1046:202:14::8, 2603:1046:804:1::8, 2a01:111:f400:2f4a::8, 2a01:111:f400:5239::8 Elapsed Time: 7 ms.
Testing TCP port 80 on host autodiscover.mybiz.com to ensure it's listening and open. The port was opened successfully. Additional Details Elapsed Time: 21 ms.
The Microsoft Connectivity Analyzer is checking the host autodiscover.mybiz.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 HTTP Response Headers: Pragma: no-cache X-FEServer: KL1PR02CA0058,KL1PR02CA0058 X-RequestId: 0d8e6a6a-3a5b-4487-8518-94a99b632f52 Connection: close Content-Length: 0 Cache-Control: no-cache Date: Thu, 12 Jan 2017 10:02:02 GMT Location: https: //autodiscover-s.outlook.com/Autodiscover/Autodiscover.xml Server: Microsoft-IIS/8.5 X-Powered-By: ASP.NET Elapsed Time: 18 ms.
Attempting to test potential Autodiscover URL https: //autodiscover-s.outlook.com/Autodiscover/Autodiscover.xml Testing of this potential Autodiscover URL failed. Additional Details Elapsed Time: 341 ms. Test Steps
Attempting to resolve the host name autodiscover-s.outlook.com in DNS. The host name resolved successfully. Additional Details IP addresses returned: 40.100.0.194, 40.100.16.18, 40.96.2.130, 40.100.20.2, 40.100.54.194, 40.100.17.18, 132.245.254.82, 132.245.43.114, 40.100.29.210, 132.245.69.34, 2a01:111:f400:2e01::2, 2603:1046:805::2, 2603:1046:804:1::2, 2603:1046:202:14::2, 2a01:111:f400:2f4a::2, 2a01:111:f400:5239::2, 2603:1046:3:15::2, 2a01:111:f400:b428::2, 2a01:111:f400:a428::2, 2603:1046:800:1::2 Elapsed Time: 10 ms.
Testing TCP port 443 on host autodiscover-s.outlook.com to ensure it's listening and open. The port was opened successfully. Additional Details Elapsed Time: 20 ms.
Testing the SSL certificate to make sure it's valid. The certificate passed all validation requirements. Additional Details Elapsed Time: 102 ms. 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=Microsoft Corporation, O=Microsoft Corporation, L=Redmond, S=WA, C=US, Issuer: CN=Microsoft IT SSL SHA2, OU=Microsoft IT, O=Microsoft Corporation, L=Redmond, S=Washington, C=US. Elapsed Time: 59 ms.
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. Elapsed Time: 1 ms.
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=Microsoft Corporation, O=Microsoft Corporation, L=Redmond, S=WA, C=US. 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=Baltimore CyberTrust Root, OU=CyberTrust, O=Baltimore, C=IE. Elapsed Time: 12 ms.
Analyzing the certificate chains for compatibility problems with versions of Windows. Potential compatibility problems were identified with some versions of Windows. Additional Details The Microsoft Connectivity Analyzer can only validate the certificate chain using the Root Certificate Update functionality from Windows Update. Your certificate may not be trusted on Windows if the "Update Root Certificates" feature isn't enabled. Elapsed Time: 2 ms.
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 = 10/13/2015 10:20:04 PM, NotAfter = 10/12/2017 10:20:04 PM Elapsed Time: 0 ms.
Checking the IIS configuration for client certificate authentication. Client certificate authentication wasn't detected. Additional Details Accept/Require Client Certificates isn't configured. Elapsed Time: 67 ms.
Attempting to send an Autodiscover POST request to potential Autodiscover URLs. Autodiscover settings weren't obtained when the Autodiscover POST request was sent. Additional Details Elapsed Time: 140 ms. 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 user.name@mybiz.com. 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). HTTP Response Headers: request-id: 763cc05b-6a51-4478-a865-097242f93e2c X-CasErrorCode: UnauthenticatedRequest X-FEServer: KL1PR02CA0045 Content-Length: 0 Cache-Control: private Date: Thu, 12 Jan 2017 10:02:03 GMT Server: Microsoft-IIS/8.5 WWW-Authenticate: Basic Realm="" X-AspNet-Version: 4.0.30319 X-Powered-By: ASP.NET Elapsed Time: 140 ms.
***************************Outlook Autodiscovery Test End***************
