Hi!

I've got ARR v3 on Windows Server 2012 R2 for external users access to Exchange 2013 (CAS,MBX).

Outlook web application works just fine, but Outlook shows "Connecting" message after entering password.

I'm using just 2 rewrite rules for mail.mydomain.com & autodiscover.mydomain.com.

I can see 401 error in Failed Requests Tracing log, but I'm not sure this is root cause of the problem.

Important notice, because it's a test environment, I'm using laptop with hosts file that contains records pointing to my ARR server external addresses mail.mydomain.com and autodiscover.mydomain.com

Production environment is still working via TMG publishing.

Any ideas how to troubleshoot this issue?

Regards, Alexey  

Hi Alexey,

In Outlook side, please run Test E-mail AutoConfiguration tool to check the autodiscover service for Outlook connection issue:

open Outlook - press CTRL key - right click on the Outlook icon from right bottom corner taskbar - Test Email AutoConfiguration. Put your email address - uncheck use guessmart and secure guessmart authentication - click Test to check your Autodiscover service.

Also make sure the certificate is configured correctly in your Exchange 2013. Please follow the articles below to check the configuration in ARR for Exchange 2013:

http://blogs.technet.com/b/exchange/archive/2013/07/19/reverse-proxy-for-exchange-server-2013-using-iis-arr-part-1.aspx

Additionally, please collect detailed error information about this issue for further analysis.

Regards,

Test Email Autoconfiguration has no errors (see attachments)

I'm not sure about Auth package - Basic. Is it ok?

I'm sure that certificate is correct because it's the same cert that web listener is using at TMG.

I've tested ARR from mobile device (Android) and it works just fine.

So the problem occurs for Outlook only.

Is there any way to enable extended logging on Outlook side?

By the way it would be nice option to choose DNS server in Outlook connectivity analyzer :) 

Regards, Alexey