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Can't connect Outlook to O365 Exchange (2 users, 1 laptop, one works, one doesn't)

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I can log in and get mail via a browser.  However when I try to set up a new account in Outlook (laptop) I get a series of error messages (can't connect to encrypted,  multiple prompts for password, etc)

 

My setup:

 

I have 2 userids and mailboxes established in O365 (P1)

 

- both can log in via web and send / receive email

 

-  userid 1 is set up in Outlook -2010 / Win7 and sends/receives email fine from my laptop

 

-  userid 2 has the problem when trying to setup in the Outlook client (same laptop/client as user 1)

 

 

I have already:

 

- run the desktop set up again

 

-  used the Connectivity Test tool to see if auto discovery is working

 

       -  User 1 / User1@mydomain.com successfully passes the auto-discovery test

       -  User2 / User2@mydomain.com FAILS the auto-discovery test

 

- the DNS is fully on O365 and a CNAME record for auto-discovery exists  (automatically set up when I add mydomain.com

 

-   manual configuration of Outlook does not work either - error message that can't connect to exchange.

 

 Help - What am I missing?   Any suggestions?

 

RJS

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  • Hi rjs,
     
    As I know non-exchange online license user will have problem on autodiscover. Please check if you have assigned an Exchange Online license for userid 2. To check license status please:

    -          Login Microsoft Online Portal

    -          Click Users under Management at right panel from Admin page

    -          Click userid 2

    -          Check licenses status under licenses status

    If that user has Exchange Online license, can you please post the connectivity test log here.
     
    Cheers,
    Te-Amo
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  • Hello Te-Amo

    Yes, Userid 2 has been assigned a license for all services (all boxes checked)

    The remote connectivy test log (Outlook 365, Autodiscovery test) is below:

    It is strange since Userid 1 passes the Connectivity test but Userid 2 fails the test - using the same laptop

    ------------------------------------------------------------------------------------

    ExRCA is attempting to test Autodiscover for Userrid2@mydomain.com.  (changed from actual)

    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 it-resultsgroup.com/.../AutoDiscover.xml

    Testing of this potential Autodiscover URL failed.

    Test Steps

    Attempting to resolve the host name it-resultsgroup.com in DNS.

    The host name couldn't be resolved.

    Tell me more about this issue and how to resolve it

    Additional Details

    Host it-resultsgroup.com couldn't be resolved in DNS InfoNoRecords.

    Attempting to test potential Autodiscover URL autodiscover.it-resultsgroup.com/.../AutoDiscover.xml

    Testing of this potential Autodiscover URL failed.

    Test Steps

    Attempting to resolve the host name autodiscover.it-resultsgroup.com in DNS.

    The host name resolved successfully.

    Additional Details

    IP addresses returned: 157.56.240.137

    Testing TCP port 443 on host autodiscover.it-resultsgroup.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.

    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.it-resultsgroup.com in DNS.

    The host name resolved successfully.

    Additional Details

    IP addresses returned: 157.56.240.137

    Testing TCP port 80 on host autodiscover.it-resultsgroup.com to ensure it's listening and open.

    The port was opened successfully.

    ExRCA is checking the host autodiscover.it-resultsgroup.com for an HTTP redirect to the Autodiscover service.

    The redirect (HTTP 301/302) response was received successfully.

    Additional Details

    Redirect URL: autodiscover-s.outlook.com/.../Autodiscover.xml

    Attempting to test potential Autodiscover URL autodiscover-s.outlook.com/.../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: 157.56.234.134, 157.56.240.86, 157.56.236.102, 157.56.244.230, 157.56.234.150, 157.56.240.102, 157.56.240.118, 157.56.240.134, 157.56.236.86, 157.56.236.118, 157.56.236.134, 157.56.244.182, 157.56.244.214, 157.56.245.6, 157.56.234.86, 157.56.234.118

    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

    ExRCA is attempting to obtain the SSL certificate from remote server autodiscover-s.outlook.com on port 443.

    ExRCA successfully obtained the remote SSL certificate.

    Additional Details

    Remote Certificate Subject: CN=outlook.com, OU=Exchange, O=Microsoft Corporation, L=Redmond, S=Washington, C=US, Issuer: CN=Microsoft Secure Server Authority, DC=redmond, DC=corp, DC=microsoft, DC=com.

    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

    ExRCA is attempting to build certificate chains for certificate CN=outlook.com, OU=Exchange, O=Microsoft Corporation, L=Redmond, S=Washington, C=US.

    One or more certificate chains were constructed successfully.

    Additional Details

    A total of 1 chains were built. The highest quality chain ends in root certificate CN=GTE CyberTrust Global Root, OU="GTE CyberTrust Solutions, Inc.", O=GTE Corporation, 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 = CN=GTE CyberTrust Global Root, OU="GTE CyberTrust Solutions, Inc.", O=GTE Corporation, 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 = 4/17/2012 9:26:21 PM, NotAfter = 4/17/2014 9:26:21 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

    ExRCA is attempting to retrieve an XML Autodiscover response from URL autodiscover-s.outlook.com/.../Autodiscover.xml for user FILName@mydomain.com.

    The Autodiscover XML response was successfully retrieved.

    Additional Details

    An HTTPS redirect was received in response to the Autodiscover request. The redirect URL is pod51011.outlook.com/.../Autodiscover.xml.

    Attempting to test potential Autodiscover URL pod51011.outlook.com/.../Autodiscover.xml

    Testing of this potential Autodiscover URL failed.

    Test Steps

    Attempting to resolve the host name pod51011.outlook.com in DNS.

    The host name resolved successfully.

    Additional Details

    IP addresses returned: 157.56.236.118, 157.56.234.134, 157.56.244.230, 157.56.240.118

    Testing TCP port 443 on host pod51011.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

    ExRCA is attempting to obtain the SSL certificate from remote server pod51011.outlook.com on port 443.

    ExRCA successfully obtained the remote SSL certificate.

    Additional Details

    Remote Certificate Subject: CN=outlook.com, OU=Exchange, O=Microsoft Corporation, L=Redmond, S=Washington, C=US, Issuer: CN=Microsoft Secure Server Authority, DC=redmond, DC=corp, DC=microsoft, DC=com.

    Validating the certificate name.

    The certificate name was validated successfully.

    Additional Details

    Host name pod51011.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

    ExRCA is attempting to build certificate chains for certificate CN=outlook.com, OU=Exchange, O=Microsoft Corporation, L=Redmond, S=Washington, C=US.

    One or more certificate chains were constructed successfully.

    Additional Details

    A total of 1 chains were built. The highest quality chain ends in root certificate CN=GTE CyberTrust Global Root, OU="GTE CyberTrust Solutions, Inc.", O=GTE Corporation, 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 = CN=GTE CyberTrust Global Root, OU="GTE CyberTrust Solutions, Inc.", O=GTE Corporation, 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 = 4/17/2012 9:26:21 PM, NotAfter = 4/17/2014 9:26:21 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

    ExRCA is attempting to retrieve an XML Autodiscover response from URL pod51011.outlook.com/.../Autodiscover.xml for user FILName@mydomain.com.

    ExRCA 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).

    Attempting to contact the Autodiscover service using the DNS SRV redirect method.

    ExRCA failed to contact the Autodiscover service using the DNS SRV redirect method.

    Test Steps

    Attempting to locate SRV record _autodiscover._tcp.it-resultsgroup.com in DNS.

    The Autodiscover SRV record wasn't found in DNS.

    Tell me more about this issue and how to resolve it

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  • Hi rjs,
     
    According to the Connectivity test log you posted above, it shows the autodiscover service works just fine. However, the error message below shows the main reason why userid2 fail the autodiscover test:
     
    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).
     
    It shows that you might enter a wrong username or password. Can you please double check the user login information and try again.
     
    Cheers,
    Te-Amo
    • Top 500 Contributor
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  • Hi rjs,

    How are things going?

    If you have any other questions or concerns, please do not hesitate to contact us. It is always our pleasure to be of assistance.

    Thanks,
    Anna Guo

    • Top 50 Contributor
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  • Still struggling.   I have re-tried with same problem:

    -  web log-on  for user 2 works

    -  connect Exchange to Outlook 10 still problem with userid / pw

    - tried to connect Outlook via IMAP/STMP and also get recurring prompt for userid / PW.

    - User 1 acess via same laptop is fine (both web and via Outlook/ Exchange)

    I'm stumped - since User 2  (id/pw) can access via web but not via Outlook and using same hardware/software as User 1 that doesn't have the problem.

    Roland

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  • create new profile for user2, Manually set up Outlook support.microsoft.com/.../2404385

    see Method 3

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  • Hi rjs,

    Does the issue still persist?

    I have done few researches on the issue and found that most users, who have similar issue, have ADFS proxy setup, therefore if you have same environment please provide more detail information about federation setup. (Like have you setup SSO proxy, have you tested the ADFS server outside.)

    Cheers,
    Te-Amo

    • Top 500 Contributor
    • Post Points: 0
  • Hi rjs,
     
    How are things going?
     
    If you have any other questions or concerns, please do not hesitate to contact us. It is always our pleasure to be of assistance.
     
    Cheers,
    Kent Gu
    • Top 100 Contributor
    • Post Points: 0
  • I am having the exact same problem for a single user. Same error with the HTTP 401 retrieving the autodiscover response. I have verified that his username/password is correct and that he is licensed. One thing to note about this user is that it was an AD account that was once deleted and then recreated with the same username. I don't see how that would affect this though.

    • Top 500 Contributor
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  • Hi tpullins,

    Based on my experience, the same problem has different situation. Please post a new thread with the detailed information about the issue in the forum. We will help you to resolve the issue.

    Thanks for your understanding.

    Thanks,

    Anna Shi

    • Top 25 Contributor
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