Hi, using outlook anywhere, basic authentication is not working for us as it keeps prompting for username and password

i have four exchange server 2013, two Mailbox and i configure DAG (which is working fine and properly), i also have two front end CAS server and i configure (NLB) which is not working, now the two CAS box are woking without any NLB. i have outlook anywhere enabled, but even for users inside or outside the domain, i need to enable windows authentication for their outlook to connect. But windows authentication automatically disables itself after some minutes, any solution to this.

thank you.

How are you setting it?

You should be using this, not setting anything in IIS:

https://technet.microsoft.com/en-us/library/bb123545%28v=exchg.150%29.aspx?f=255&MSPPError=-2147217396

Hi, using outlook anywhere, basic authentication is not working for us as it keeps prompting for username and password

i have four exchange server 2013, two Mailbox and i configure DAG (which is working fine and properly), i also have two front end CAS server and i configure (NLB) which is not working, now the two CAS box are woking without any NLB. i have outlook anywhere enabled, but even for users inside or outside the domain, i need to enable windows authentication for their outlook to connect. But windows authentication automatically disables itself after some minutes, any solution to this.

thank you.

Basic authentication will always prompt for a username and password.  If you do not want to be prompted for this information (I'm assuming you are only using Domain joined machines) then you will need to configure NTLM as your authentication methods for Outlook Anywhere.

Hi,

What's your Outlook Anywhere configuration? Please run the following command to have a check:

Get-OutlookAnywhere | fl

We can try the following settings:

Set-OutlookAnywhere -Identity "Exch13\Rpc (Default Web Site)" -InternalHostname mail.domain.com -ExternalHostname mail.domain.com -InternalClientAuthenticationMethod Ntlm -ExternalClientAuthenticationMethod Basic -ExternalClientsRequireSsl $True -InternalClientsRequireSsl $true

If the authentication is set to Basic, the credential would be always prompted when you open the Outlook. If it still doesn't work though you have input the right username and password, please clear the credentials caches in Credential Manager of Control Pane to have a try.

If the issue happens to all users instead of specific users, please run the Microsoft Remote Connectivity Analyzer to check the autodiscover service and Outlook connectivity to have a try:

https://testconnectivity.microsoft.com/

Regards,