1 files changed, 27 insertions, 0 deletions
diff --git a/test/webrick/test_ssl_server.rb b/test/webrick/test_ssl_server.rb
index f6d5250365..64cf25f78b 100644
--- a/test/webrick/test_ssl_server.rb
+++ b/test/webrick/test_ssl_server.rb
@@ -2,6 +2,7 @@ require "test/unit"
 require "webrick"
 require "webrick/ssl"
 require_relative "utils"
+require 'timeout'
 
 class TestWEBrickSSLServer < Test::Unit::TestCase
   class Echo < WEBrick::GenericServer
@@ -37,4 +38,30 @@ class TestWEBrickSSLServer < Test::Unit::TestCase
       io.close
     }
   end
+
+  def test_slow_connect
+    poke = lambda do |io, msg|
+      begin
+        sock = OpenSSL::SSL::SSLSocket.new(io)
+        sock.connect
+        sock.puts(msg)
+        assert_equal "#{msg}\n", sock.gets, msg
+      ensure
+        sock&.close
+        io.close
+      end
+    end
+    config = {
+      :SSLEnable => true,
+      :SSLCertName => "/C=JP/O=www.ruby-lang.org/CN=Ruby",
+    }
+    Timeout.timeout(10) do
+      TestWEBrick.start_server(Echo, config) do |server, addr, port, log|
+        outer = TCPSocket.new(addr, port)
+        inner = TCPSocket.new(addr, port)
+        poke.call(inner, 'fast TLS negotiation')
+        poke.call(outer, 'slow TLS negotiation')
+      end
+    end
+  end
 end