Hi @TonyJK ,
Can you explain the relationship between servername and servername.company.com and what them are?
According to my understanding, servername is IP of server and servername.company.com is the host name of site on server. Is it right?
If so, did you add "127.0.0.1 servername.company.com" in hosts file of windows server? You also need to add "xxx.xxx.xxx servername.company.com"(xxx.xxx.xxx is the IP of windows server) in hosts file of client machine.
If not, check log of site to see if server receive the request. If it received the request, check the substatus code and refer to this docs. You will know what cause 404.
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Best regards,
Bruce Zhang