Exchange 2010 to 2013 Migration "Outlook is unable to connect to the proxy server. (Error Code 10)" and login prompt

While attempting to migrate to Exchange 2013 we ran into a problem.  We mostly have Outlook 2007 clients with a handful of Outlook 2010 clients.  All the mailboxes that have been migrated to the 2013 server and have Outlook 2007 are getting the  "Outlook is unable to connect to the proxy server. (Error Code 10)" and login prompt.  All of the mailboxes on 2013 with Outlook 2010 work without any issues.  All connections from the outside (OWA and Outlook Anywhere) work without issues.  The only problem is with Outlook 2007 on our internal network.  We have a multi-domain certificate pointing to the outside for OWA and Autodiscover.  We have split DNS set up with OWA pointing to the inside 2013 server ip address.  Outlook 2007 and 2010 are getting the same correct information from autodiscover.  I have tried creating a new Outlook profile without any luck.

Is this Microsoft's way of killing Office 2007?

Any suggestions??


  • Edited by j_p_76 Wednesday, August 19, 2015 8:45 PM
August 19th, 2015 8:06pm

Hi,

Please run the below command:

Get-OutlookProvider

For Autodiscover service, please run Test E-mail AutoConfiguration to check if the connection is successful in Log tab and confirm the other services URL can use proper namespace in Results tab for request access.

If the Autodiscover service fails, please create a SRV record with mail.domain.com for Autodiscover service to have a try.

In addiction, I have found a similar thread for your reference:

https://social.technet.microsoft.com/Forums/office/en-US/a8e6a8d6-8600-42e7-bdfc-8aaa8ad8b467/outlook-is-unable-to-connect-to-the-proxy-server-error-code-10?forum=exchangesvrclients

Regards,

David 

  • Marked as answer by j_p_76 11 hours 39 minutes ago
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August 20th, 2015 2:32am

Hi,

Please run the below command:

Get-OutlookProvider

For Autodiscover service, please run Test E-mail AutoConfiguration to check if the connection is successful in Log tab and confirm the other services URL can use proper namespace in Results tab for request access.

If the Autodiscover service fails, please create a SRV record with mail.domain.com for Autodiscover service to have a try.

In addiction, I have found a similar thread for your reference:

https://social.technet.microsoft.com/Forums/office/en-US/a8e6a8d6-8600-42e7-bdfc-8aaa8ad8b467/outlook-is-unable-to-connect-to-the-proxy-server-error-code-10?forum=exchangesvrclients

Regards,

David 

  • Marked as answer by j_p_76 Friday, August 21, 2015 7:48 PM
August 20th, 2015 2:32am

Hi David

When I run Get-Outlook Provider I get the CertPrinicipalName pointing to the outside address that is on the certificate for EXPR.  In Test E-mail AutoConfiguration Log it says that Autodiscover to the outside Autodiscover address succeeded.  On the results tab it has the correct outside address for all the other services.  I had already created a SRV record for Autodiscover last week while troubleshooting.

I had already found the thread that you linked to.  All those setting are also correct.

Thanks,

Jeff

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August 20th, 2015 10:10am

I figured it out.  When I had update the internal url for Outlook-Anywhere it didn't change the setting for the Exchange 2010 Server.  I ran the same command again and it changed it to the same thing as the Exchange 2013 Server.

Thanks,

Jeff

  • Marked as answer by j_p_76 11 hours 39 minutes ago
August 21st, 2015 3:51pm

I figured it out.  When I had update the internal url for Outlook-Anywhere it didn't change the setting for the Exchange 2010 Server.  I ran the same command again and it changed it to the same thing as the Exchange 2013 Server.

Thanks,

Jeff

  • Marked as answer by j_p_76 Friday, August 21, 2015 7:48 PM
Free Windows Admin Tool Kit Click here and download it now
August 21st, 2015 7:47pm

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