Hi!

Some info:

• 2x AD/DC Windows 2003 Native.
  
• Previous Exchange 2003 installed, but now cleanly as it gets uninstalled.

• Exchange 2013CU2v2 Aka Version 15.0 (Build 712.24)
  
• Office 2010 with Outlook 2010 (Latest SP, and WU)
  
• Outlook-prf configured for Outlook Anywhere. (i've also tried to configure manually, no difference)
  
• Exchange: SAN Cert. GUI requested from ECP. This one covers all possible host names the server can use. autodiscover, owa, mail, "netbios"-name. Self issued from the internal CA. CA distributed to clients with GPO. I get NO certificate warnings surfing to OWA, ECP.
  
  
• Exchange: ECP/Server/Outlook Anywhere; Auth set to NTLM (not Negotiate)
  
• Ping inside host names resolves to the Exchange server.
  
  
• Starting Outlook.exe with /rpcdiag show two connections for a while. One of the type catalog and one of the type redirect.
  

Problem:

1. When starting Outlook you see "Loading profile" for about 30-40 seconds. /rpcdiag show two connections CID "9","11"; SERVERNAME "---","[GUID]@thedomain", AUTH and ENCRYPT is empty.
2. The the a dialog comes up that says that the server isn't available?!
3. Clicking "Retry" makes Outlook connect as it should. Everything from there works like a charm! /rpcdiag windows show that it has connection as it should.

Tried to click "Reconnect" in /rpcdiag. It also takes about 30 sec before it regains the conneciton. The part hanging there is the Type: Redirect.

So, does anyone have a clue for why it doesn't work and then does?

Can it be something wrong with the autodiscover?

Hello,

Do you mean the issue occurs when you select manually configure outlook exchange account or automatically configure outlook exchange account? If so, please make sure whether all users have the issue.

I recommend you check if there exists redirection on your rpc virtual directory.

I recommend you use "test e-mail autoconfiguration" tool to check if your autodiscover is correct.

Besides, I recommend you to enable global and advanced logging for outlook to check RPC trace events.

How to enable global and advanced logging for Outlook 2010 and Outlook 2013

http://support.microsoft.com/kb/2260527

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I know this was forever ago, but if you are still monitoring responses, I'd like to know what you did to resolve the issue. I'm having the same thing now. I think it is because Outlook it taking forever to stop trying to connect to the DC over TCP/IP and switch over to the Exchange server as a proxy over HTTPS to the DC. I don't know how to force Outlook to either A. timeout on that DC faster, or B. Go directly to Exchange as a proxy.

I just ran into this and it turned out to be the proxy (PAC) file not availble, Outlook in online mode would not connect on launch, hitting retry would connect.  Outlook in cached mode would connect just fine without the PAC file available.  Removing the PAC file from Internet Options allowed normal connectivity.