diff --git a/ChangeLog b/ChangeLog
index 93c11a92ef..d6150a7eaa 100644
--- a/ChangeLog
+++ b/ChangeLog
@@ -1,3 +1,7 @@
+Wed Apr 23 00:36:03 2008  Yusuke Endoh  <mame@tsg.ne.jp>
+
+	* test/openssl/test_ssl.rb (start_server): add timeout to server.join.
+
 Wed Apr 23 00:18:45 2008  Kazuhiro NISHIYAMA  <zn@mbf.nifty.com>
 
 	* test/ruby/test_symbol.rb (TestSymbol#test_to_proc): Improve
diff --git a/test/openssl/test_ssl.rb b/test/openssl/test_ssl.rb
index b1bbc656dd..fe7327604f 100644
--- a/test/openssl/test_ssl.rb
+++ b/test/openssl/test_ssl.rb
@@ -129,7 +129,14 @@ class OpenSSL::TestSSL < Test::Unit::TestCase
       block.call(server, port.to_i)
     ensure
       tcps.close if (tcps)
-      server.join if (server)
+      if (server)
+        server.join(5)
+        if server.alive?
+          server.kill
+          server.join
+          flunk("TCPServer was closed and SSLServer is still alive") unless $!
+        end
+      end
     end
   end