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Security layer issue

I have a collection of two RDS virtual servers RDS01 & RDS02 under Windows Server 2008 R2 and one RDS/REMOTEAPP virtual server APP01 under Windows Server 2012 R2.

  • RDS01 & RDS02 has the same configuration
  • RDS01 & RDS02 can ping APP01
    • ping APP01.domain.local OK
  • RDS01 & RDS02 can establish a connection to APP01 via 443 or 3389 port
    • telnet APP01.domain.local 443 OK
    • telnet APP01.domain.local 3389 OK
  • RDS01 can connect to APP01 via HTTPS/RDS
    • https://APP01.domain.local/rdweb OK
    • mstsc > APP01.domain.local OK
  • RDS02 cannot connect to APP01 via HTTPS/RDS
    • https://APP01.domain.local/rdweb TIMEOUT
    • mstsc > APP01.domain.local TIMEOUT

I suspect a security layer negotiation issue but I have no idea how to solve this problem.

  • In Internet Explorer, TLS 1.0 / 1.1 / 1.2 protocols are enabled in Internet Settings.
  • In MSTSC application, prompt for credentials opens and after validate, a connection progress bar run infinitely and display: Securing remote connection

enter image description here

Any help will be welcome

Edit 1: An interesting article about this issue:


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