SSMS cannot connect remote server by IP through Windows authentication I'm trying to connect a remote server by IP,port via Windows authentication.
It will end out with the following error


  Connection Timeout Expired.  The timeout period elapsed while
  attempting to consume the pre-login handshake acknowledgement.  This
  could be because the pre-login handshake failed or the server was
  unable to respond back in time.  The duration spent while attempting
  to connect to this server was - [Pre-Login] initialization=41306;
  handshake=27677;  (Microsoft SQL Server, Error: -2)


However, if connect to IP,port but login with sa through SQL Server authentication then I can connect to the server correctly.

Moreover, if I switch to MachineName,port and login via Windows authentication then I can successfully connect too.

Not sure what kind of setting/adjustment I need to make this use case work.

Environment


My laptop is Win10 and the SQL Server 2012 is on a Windows server 2012 R2
These two machines are in the same domain.
We are using another port instead of default 1433.


Case I tried


remote IP,port via Windows authentication - failed
remote MachineName,port via Windows authentication - successful
remote IP,port via SQL Server authentication(sa account) - successful
remote IP\MSSQLSERVER,port via Windows authentication - failed
RDP to remote then use ssms there IP,port via Windows authentication - successful


Setting I have tried


Add the SQL Server exe to the inbound rule
Launch SQL Server browser
Change IP1 to the IPv4 I'm using and Active/Enabled it(restart service too)
Make sure TCP/IP are enabled on Protocols of MSSQLSERVER and Client Protocols(/32bit)
Add the port I'm using to IPAll/TCP Port and keep Dynamic ports blank
So it turns out the timeout is actually a timeout...
After I expend the connection timeout to 90 sec it connected after about a minute.

Infrastructure guys say this might since it's trying to resolve the machine name or something? (I'm not really familiar with network and setting stuff).
I will update this answer if they figure out any way to speed up the process.