I have a new install of Windows 2012.  I have two physical servers.  One is a W2012 std Domain Controller ("DC").  The Second is configured as W2012 HyperV  ("HV").  Under HV I have two VMs.  One VM is W2012/Exchange 2013 ("ExchVM) and the other is W2012/Terminal Server ("VMTS").  All systems are behind a firewall appliance.  Exchange is working via Outlook and OWA internally and externally.  The self created SSL must be installed manually on external machines since it comes up as an untrusted certificate.  Once installed remote outlook works and OWA works.  I have configured the terminal server and I am able to login remotely as various users under my "TS group".  The problem is when ever I attempt to open Outlook for the 1st time, it fails to connect to the exchange server.   (Open Outlook 2013, click next on the splash screen, "Yes" Add an Email Account splash screen, click next, Auto Account screen populates NAME and Email Address correctly, click next, Searching for mail server settings..., check on establishing network connection, check on searching for alias@ domain, then fails the logging on to the mail server)  The error reads:  "Outlook cannot log on.  Verify you are connected to the network and are using the proper server and mailbox name.  The connection to Microsoft Exchange is unavailable.  Outlook must be online or connected to complete this action."   I am connected in RDS from offsite, and from the RD session I can access shared folders on ExchVM and DC.  I have tried have verified the server Exchange server name is correct via "Get=ClientAccessServer" command.  I have also tried to use the guid via "Get-Mailbox ALIAS | fl name, exchangeguid.  Keep in mind all desktop users on the network are connecting to Outlook without issue.

I would appreciate any thoughts on solving this issue.

I found a workaround, but I am still interested in a proper fix. I am leaning toward reconfiguring autodiscover.

I attempted to manually configure mail thru Control Panel> User Accounts..> Mail.  I noticed under "more settings">Connection, Exchange Proxy was not configured.  Once I configured the exchange proxy settings and manually installed the SSL in each profile I was able to then launch Outlook successfully.   

I suspect the autodiscover/ssl are not playing well.  At the moment I will use the workaround.  I look forward to suggestions to solving this problem.  I need a break!

I found a workaround, but I am still interested in a proper fix. I am leaning toward reconfiguring autodiscover.

I attempted to manually configure mail thru Control Panel> User Accounts..> Mail.  I noticed under "more settings">Connection, Exchange Proxy was not configured.  Once I configured the exchange proxy settings and manually installed the SSL in each profile I was able to then launch Outlook successfully.   

I suspect the autodiscover/ssl are not playing well.  At the moment I will use the workaround.  I look forward to suggestions to solving this problem.  I need a break!

• Proposed as answer by Winnie LiangMicrosoft contingent staff 4 hours 25 minutes ago

Hi,

According to your workaround, it seems that the Outlook Anywhere configuration in Outlook client is not correct when using the Autodiscover service.

Once you connected to Exchange server by manually settings, please run Test E-mail AutoConfiguration tool in external Outlook client to check the autodiscover service:

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.

Please check the Log tab and confirm whether the Autodiscover service is connected successfully. Also confirm if the connection issue happens to all external users when they open Outlook for the 1st time. In Exchange server, please make sure autodiscover.domain.com has been included in your Exchange certificate which is assigned with IIS service.

Regards,