Hello. I have smartermail installed on a webserver that I want to use with outlook and autodiscover. Webmail works fine
Domain: my domain.local
Mail url is mail.mydomian.local and takes me to the webmail page, as does autodiscover.mydomain.local
Both are over https on 443 with a valid cert for both urls
Smartermail is configured for AD authentication
It's important to note this network is closed. Meaning no Internet access and I have my own CA (which works fine)
Autodiscover doesn't seem to work. I open outlook for my logged in account, select exchange. I then get a basic windows pop-up for username and password that just keeps popping up. If I hit cancel, I get asked to trust autodiscover.xml, but it does not configure properly.
Now the twist, if I login to the webmail client first with the account I want to use, then the Outlook setup will then complete flawlessly with only entering username and password once.
Any idea as to why? The autodiscover detailed log shows unable to parse ntlmmessage1 and unauthorized negotiate for the failed attempts. The IIS site only has anon login enabled, the others are disabled so I'm not sure exactly that's coming from. Thanks!