Hello,

On my 2010 server autodiscover would let you fill in your name and address on the first part of a new outlook profile.  Then it would complete the autodiscover with the 3 checks

Establish network connection

Search for yourname@yourdomain.com server settings

Log On to Server

On my 2013 server, when setting up an outlook profile, you fill in the user name, email address and password then click next it starts the autodiscover process,

It passes establish network connection, search for yourname@yourdomain.com server settings

But then, it prompts for the username and password before it gets to the third checkbox - Log on to server.

If you fill in your email address and password again it will pass that third check box successfully but I don't want to have end users having to fill out their account login and password twice.

Does anyone know what I need to fix so it no longer prompts you at that point?

Exchange 2013 use only https access from Outlook. Logon prompt could be related to Basic Authentication set in Outlook anywhere config or some Kerberos problems.

Thanks.

So you are saying in 2013, I should turn basic authentication off in outlook anywhere?   In ECP, Servers, settings - change it to NTLM or negotiate?   I think I had it on negotiate initially and it had issues.

Any changes in IIS?

Hi  

Do you create a new profile or use the existing profile ?

If this is a new profile , it is expected behavior . if no , please try to Change Proxy authentication from Basic to NTLM authentication on Outlook client.

Outlook 2010 asks for username and password twice on first run<//span>:

http://social.technet.microsoft.com/Forums/en-US/outlook/thread/631677b1-2789-41bf-accc-3888c3c78843/

Hello,

I'm not sure if you are speaking of a new outlook profile or exchange profile.   In either case, it did not ask for this on the 2010 exchange servers I set up in the past.  Users are not happy with the double authentication on the 2013 server I just set up.  

Hi,
Can you revert the default settings for Outlook Anyware back?
In the below output you'll see the default setting for the authentication methods. I have changed the InternalHostname to be the same as the Externalhostname.

[PS] C:\>Get-OutlookAnywhere | fl *hostname,*auth*

ExternalHostname                   : mail.domain.com
InternalHostname                   : mail.domain.com
ExternalClientAuthenticationMethod : Negotiate
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods           : {Basic, Ntlm, Negotiate}

hi,

Can anyone say it is good or not, i got two results confused about it, why two? and why different?

steps below of what i did.

check authentication method.

[PS] C:\Windows\system32>Get-OutlookAnywhere -Server exch | fl *External*

ExternalHostname                   : exch.kbrokerage.com
ExternalClientAuthenticationMethod : Negotiate
ExternalClientsRequireSsl          : True


[PS] C:\Windows\system32>Get-OutlookAnywhere -Server exch | fl *Internal*

InternalHostname                   : exch.kbrokerage.com
InternalClientAuthenticationMethod : Negotiate
InternalClientsRequireSsl          : True

change to Ntlm.

[PS] C:\Windows\system32> Set-OutlookAnywhere -Identity "exch\RPC (Default Web Site)" -ExternalHostname "exch.kbrokerage.com" -ExternalClientAuthenticationMethod ntlm -ExternalClientsRequireSsl $true

[PS] C:\Windows\system32>Set-OutlookAnywhere -Identity "exch\RPC (Default Web Site)" -InternalClientAuthenticationMethod ntlm -InternalClientsRequireSsl $true

confirm changes

[PS] C:\Windows\system32>Get-OutlookAnywhere -Server exch | fl *External*

ExternalHostname                   : exch.kbrokerage.com
ExternalClientAuthenticationMethod : Ntlm
ExternalClientsRequireSsl          : True

[PS] C:\Windows\system32>Get-OutlookAnywhere -Server exch2013 | fl *Internal*


InternalHostname                   : exch.kbrokerage.com
InternalClientAuthenticationMethod : Ntlm
InternalClientsRequireSsl          : True

but this below result can any one explain me, and guide me to right direction.

[PS] C:\Windows\system32>get-outlookanywhere |fl *hostname,*auth*

ExternalHostname                   : exch.kbrokerage.com
InternalHostname                   : exch.kbrokerage.com
ExternalClientAuthenticationMethod : Ntlm
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods           : {Negotiate}

ExternalHostname                   :
InternalHostname                   : exch.kbrokerage.com
ExternalClientAuthenticationMethod : Negotiate
InternalClientAuthenticationMethod : Ntlm
IISAuthenticationMethods           : {Basic, Ntlm, Negotiate}