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Outlook username/password prompt

Posted on 2014-02-24
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Last Modified: 2014-03-06
I have just finished a migration from 2007 to 2013.  It's been terrible, just went through a lot of problems. For the most part, most things are working, except, all external users, are being prompted for a username/password prompt.  Even though they enter their credentials, it still prompts them.

I made sure and the accounts are NOT locked out.

I even deleted the outlook profile, even deleted the ost file, still nothing.
I even found on a post the following:
      1. Start CMD: type the following:  control/name Microsoft.credentialmanager
      2. Look for anything that looks like Msoutlook:emailaddress….               (remove it from the vault)
      3. Restart Outlook (if prompted, enter the user/pass again)

Still doesn't work. On one of the PCs, I even upgraded to outlook 2013, and it still didnt' work.  Not sure what else to do?

I already shutdown my exchange 2007, but I don't think that has anything to do with it, because it was causing other routing problems internally, so as soon as I shut it down, it fixed my other problem.

Any ideas?  I have about 7 or 8 remote users that are experiencing this issue.

Thanks, Dan
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Question by:afacts
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jbvernej earned 500 total points
ID: 39885130
hello

Authentication popup are the big huge problem in outlook /exchange migration as these  issues have a lot of root causes.

mainly, this popup are related to the authentication config (NTLM/ Basic/Kerberos/Anonymous) on the Exchange server CAS's side, when they don't match the Outlook's side.

You can check your outside's (internet) Exchange config with the Microsoft Connectivity Analyzer: http://www.exrca.com
If its test & report does pass (all main items should be displayed as green), your config on the Exchange's side should be fine.
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Author Comment

by:afacts
ID: 39886595
I went to https://testconnectivity.microsoft.com/

And here's the output. So what exactly do I need to do, something with an external autodiscover DNS entry I think, but where would I point that to?



Testing RPC/HTTP connectivity.
The RPC/HTTP test failed.
Additional Details
Elapsed Time: 1635 ms.
Test Steps
The Microsoft Connectivity Analyzer is attempting to test Autodiscover for user@mydomain.org.
Testing Autodiscover failed.
Additional Details
Elapsed Time: 1634 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: 1634 ms.
Test Steps
Attempting to test potential Autodiscover URL https://mydomain.org/AutoDiscover/AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Additional Details
Elapsed Time: 1012 ms.
Test Steps
Attempting to resolve the host name mydomain.org in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: ext_IP_117.180
Elapsed Time: 243 ms.
Testing TCP port 443 on host mydomain.org to ensure it's listening and open.
The port was opened successfully.
Additional Details
Elapsed Time: 204 ms.
Testing the SSL certificate to make sure it's valid.
The certificate passed all validation requirements.
Additional Details
Elapsed Time: 235 ms.
Test Steps
The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server mydomain.org on port 443.
The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
Additional Details
Remote Certificate Subject: CN=*.mydomain.org, O="mydomain.", L=mytown, S=CA, C=US, Issuer: SERIALNUMBER=07969287, CN=Go Daddy Secure Certification Authority, OU=http://certificates.godaddy.com/repository, O="GoDaddy.com, Inc.", L=Scottsdale, S=Arizona, C=US.
Elapsed Time: 147 ms.
Validating the certificate name.
The certificate name was validated successfully.
Additional Details
Host name mydomain.org 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=*.mydomain.org, O="mydomain.", L=mytown, S=CA, 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 OU=Go Daddy Class 2 Certification Authority, O="The Go Daddy Group, Inc.", C=US.
Elapsed Time: 30 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: 4 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 = 10/4/2011 10:57:57 PM, NotAfter = 10/4/2014 10:57:57 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: 226 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://mydomain.org/AutoDiscover/AutoDiscover.xml for user user@mydomain.org.
The Microsoft Connectivity Analyzer failed to obtain an Autodiscover XML response.
Additional Details
A Web exception occurred because an HTTP 417 - ExpectationFailed response was received from Unknown. Headers received: Content-Length: 0 Date: Tue, 25 Feb 2014 18:48:13 GMT Server: Microsoft-IIS/7.5 X-Powered-By: ASP.NET
Elapsed Time: 101 ms.
Attempting to test potential Autodiscover URL https://autodiscover.mydomain.org/AutoDiscover/AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Additional Details
Elapsed Time: 310 ms.
Test Steps
Attempting to resolve the host name autodiscover.mydomain.org in DNS.
The host name couldn't be resolved.
Tell me more about this issue and how to resolve it
Additional Details
Host autodiscover.mydomain.org couldn't be resolved in DNS InfoDomainNonexistent.
Elapsed Time: 310 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: 23 ms.
Test Steps
Attempting to resolve the host name autodiscover.mydomain.org in DNS.
The host name couldn't be resolved.
Tell me more about this issue and how to resolve it
Additional Details
Host autodiscover.mydomain.org couldn't be resolved in DNS InfoDomainNonexistent.
Elapsed Time: 23 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: 143 ms.
Test Steps
Attempting to locate SRV record _autodiscover._tcp.mydomain.org 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: 143 ms.
Checking if there is an autodiscover CNAME record in DNS for your domain 'mydomain.org' for Office 365.
Failed to validate autodiscover CNAME record in DNS. If your mailbox isn't in Office 365, you can ignore this warning.
Tell me more about this issue and how to resolve it
Additional Details
There is no Autodiscover CNAME record for your domain 'mydomain.org'.
Elapsed Time: 143 ms.
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Author Closing Comment

by:afacts
ID: 39910248
Thanks for your willingness, I called Microsoft and almost everything the tech did was in IIS.

It's resolved now.
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