have outlook anywhere up and running.. the parent domain mail.domain.net users can use outlook fine outside and inside the network, but when I setup a user from (a)domain2 the user will get all the way to authentication prompt but it just keeps asking for prompt. Weird thing is I redid the SSL cert due to someone revoking it and it all worked for a few days fine, now it just prompting for passwords again. I ran Microsoft Remote Connectivity Test and all pass with green lights.. I looked at the XML and seems like all the correct info is sent, but for OUTLOOK it just won't work.. OWA works fine as well..

Anyone got any experience with a similar issue? going insane already, been trying to fix this server for days already and every time I seem to have it working it just starts acting up again.

Did you run Setup /PrepareAllDomains when installing or upgrading?

Hi,

I noticed that the issue only happens when the child domain users connect to Exchange server by using Outlook Anywhere.

Please run Test E-mail AutoConfiguration tool in the problematic client side to check the detailed connection for 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 collect the Log tab information here for further analysis.

Regards,