Outlook 2010 can't connect to Exchange.

I'm stumped, and wonder if anyone has any suggestions.

I am trying to connect to a newly installed Exchange 2013 server using Outlook 2010 on a Windows 7 pro 64-bit client.

Here's the sequence of events.
I fire up Outlook, tell it to create a new profile, choose Manually configure Server, choose Microsoft Exchange, Type the name of the server (I've tried both short and fqdn name), type the user name (tried both the user name and the full email address).

When I hit Check Name or hit Next, the dialog box I get is:
"The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action." I tried to upload a screencap, but my account apparently isn't verified.

I've searched for similar issues, and based on the questions and solutions in other threads, here are the answers to the most likely questions:

  • Windows firewall is disabled both on the server and the client.
  • I'm on the same network subnet
  • DNS works, I can ping the server by both short name and fqdn from the client.
  • HTTPS to OWA works, I can log into the account and send/receive email.
  • I'm using a self-signed cert, but I have installed that cert to the client computer as a trusted cert, and OWA does not show any cert errors.
  • This server port 443 is not directly reachable via the internet due to an external firewall, but all ports are available to the LAN segment where the client is located. Also DNS and SMTP traffic is flowing back and forth to the internet just fine.
  • Unchecking Cached mode doesn't work either.
  • Auto-configure is not set up yet, that's why I'm going manual. Using any of the external connectivity checkers will be futile.

So, does anyone have any ideas? 

Edit: I apparently am not allowed to  upload images yet, so no screenshot. 
And yes, my client and server both have a default gateway


  • Edited by CB in Mont Saturday, February 21, 2015 2:50 AM more info, correction
February 21st, 2015 5:37am

Hi,

When we configure our account in Exchange 2013 environment, the server name option is filled with user mailbox GUID +@+user primary SMTP address.

Thanks
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February 23rd, 2015 9:44am

Thank you for the thought, but no, that isn't going to help.  Outlook2010-kb2597011 is a post-sp1, pre-sp2 hotfix.  My system is patched to the most current state via Windows Update, including SP2.

Just on the off chance that wasn't the case, I downloaded the Hotfix from your referenced article, and tried installing it.

It refused to install, with a dialog box that said "The update is already installed on this system"


February 23rd, 2015 6:31pm

I imagine your account is configured via auto-configure?

As I said, I'm doing this by creating a new profile in Outlook from scratch, and doing so manually since Auto-configure isn't set up yet (my legacy server is still handling email, and I don't want to switch until I can get a test account or two working)

I did try getting the user mailbox GUID from the Exchange 2013 server, and manually pasted the GUID +@+user primary SMTP address into the configuration dialog boxes, but observed no difference in the behavior of Outlook.

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February 23rd, 2015 6:36pm

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