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It is definitely possible to establish a secure SSL/TLS connection on Windows Server 2016. Windows Server 2016 supports SSL/TLS protocols 1.0, 1.1, and 1.2, and it has built-in features for configuring and managing SSL/TLS certificates. Additionally, popular web servers like IIS (Internet Information Services) can be configured to use SSL/TLS for secure communication. However, it is important to note that SSL/TLS security also depends on the supporting applications and libraries, and the configuration has to be done carefully to ensure maximum security.