diff --git a/lib/webrick/server.rb b/lib/webrick/server.rb
index 2d678273e5..57ffe5a48b 100644
--- a/lib/webrick/server.rb
+++ b/lib/webrick/server.rb
@@ -295,12 +295,14 @@ def start_thread(sock, &block)
           end
           if sock.respond_to?(:sync_close=) && @config[:SSLStartImmediately]
             WEBrick::Utils.timeout(@config[:RequestTimeout]) do
-
-              # we must call OpenSSL::SSL::SSLSocket#accept_nonblock until
-              # it stop returning wait_* symbols:
+              
+              # we must call OpenSSL::SSL::SSLSocket#accept_nonblock until it
+              # stops returning wait_* symbols
+              # accept_nonblock can only be called once on Windows
               case ret = sock.accept_nonblock(exception: false)
               when :wait_readable, :wait_writable
                 sock.to_io.__send__(ret)
+                break if /mingw|mswin/ =~ RUBY_PLATFORM
               else
                 break
               end while true