diff --git a/lib/asciidoctor-diagram/util/java_socket.rb b/lib/asciidoctor-diagram/util/java_socket.rb
index 5f151790..16287ef8 100644
--- a/lib/asciidoctor-diagram/util/java_socket.rb
+++ b/lib/asciidoctor-diagram/util/java_socket.rb
@@ -13,9 +13,16 @@ def initialize(java, classpath)
           args = []
           args << '-Djava.awt.headless=true'
           args << '-cp'
-          args << classpath.flatten.join(File::PATH_SEPARATOR)
+		  # special case for cygwin, it requires path translation for java to work
+		  cygpath = ::Asciidoctor::Diagram.which('cygpath')
+		  if(cygpath != nil) 
+		    args << classpath.flatten.map { |jar| `cygpath -w "#{jar}"`.strip }.join(";")
+		  else	
+			args << classpath.flatten.join(";")
+	      end
           args << 'org.asciidoctor.diagram.CommandServer'
-
+          puts "ARGS:"
+          puts args
           @server = IO.popen([java, *args])
           @port = @server.readline.strip.to_i
           @client = TCPSocket.new 'localhost', port