ElasticSearch 2.2.0 and the corresponding search-guard-ssl-2.2.0.6 are installed.
In desperation I have also downloaded and compiled apr-1.5.2 (./configure, make, make install in cygwin's terminal window) into /usr/local/apr and added the bin and lib directories to PATH but to no avail. netty-tcnative-1.1.33.Fork13-windows-x86_64.jar is in the plugins/search-guard-ssl folder.C:\cigwin64\bin\opennssl.exe (runs well in cygwin's terminal window).C:\cigwin64\bin\cygaprutil-1-0.dll (I have also copied it and renamed it aprutil-1-0.dll).C:\cigwin64\bin\cygapr-1-0.dll (I have also copied it and renamed it apr-1-0.dll).I have verified the installation of APR and OpenSSL at the following locations: Open SSL not available because of : C:\cygwin64\tmp\netty-tcnative5452582727732685820.dll: Can't find dependent libraries Until this gets resolved you may want to disable OpenSSL support and go with Java built in SSL: This sound more like a netty/netty-tcnative problem.