diff --git a/ChangeLog b/ChangeLog
index 21eab9aca2..48dc05d311 100644
--- a/ChangeLog
+++ b/ChangeLog
@@ -1,3 +1,10 @@
+Wed May 28 18:06:13 2014  Tanaka Akira  <akr@fsij.org>
+
+	* ext/openssl/ossl_ssl.c (ossl_ssl_close): Fix sync_close to work
+	  when SSL is not started.
+	  This fix the fd leak by test_https_proxy_authentication in
+	  test/net/http/test_https_proxy.rb.
+
 Wed May 28 10:29:28 2014  Eric Wong  <e@80x24.org>
 
 	* vm.c (rb_vm_living_threads_foreach): remove function
diff --git a/ext/openssl/ossl_ssl.c b/ext/openssl/ossl_ssl.c
index a95ab3d1d0..f314a7ac25 100644
--- a/ext/openssl/ossl_ssl.c
+++ b/ext/openssl/ossl_ssl.c
@@ -1566,18 +1566,22 @@ static VALUE
 ossl_ssl_close(VALUE self)
 {
     SSL *ssl;
+    VALUE io;
 
-    ossl_ssl_data_get_struct(self, ssl);
+    /* ossl_ssl_data_get_struct() is not usable here because it may return
+     * from this function; */
 
-    if (ssl) {
-	VALUE io = ossl_ssl_get_io(self);
-	if (!RTEST(rb_funcall(io, rb_intern("closed?"), 0))) {
-	    ossl_ssl_shutdown(ssl);
-	    SSL_free(ssl);
-	    DATA_PTR(self) = NULL;
-	    if (RTEST(ossl_ssl_get_sync_close(self)))
-		rb_funcall(io, rb_intern("close"), 0);
-	}
+    Data_Get_Struct(self, SSL, ssl);
+
+    io = ossl_ssl_get_io(self);
+    if (!RTEST(rb_funcall(io, rb_intern("closed?"), 0))) {
+        if (ssl) {
+            ossl_ssl_shutdown(ssl);
+            SSL_free(ssl);
+        }
+        DATA_PTR(self) = NULL;
+        if (RTEST(ossl_ssl_get_sync_close(self)))
+            rb_funcall(io, rb_intern("close"), 0);
     }
 
     return Qnil;
diff --git a/test/openssl/test_ssl.rb b/test/openssl/test_ssl.rb
index 23dc572870..e99d3d9786 100644
--- a/test/openssl/test_ssl.rb
+++ b/test/openssl/test_ssl.rb
@@ -680,6 +680,15 @@ end
     }
   end
 
+  def test_sync_close_without_connect
+    Socket.open(:INET, :STREAM) {|s|
+      ssl = OpenSSL::SSL::SSLSocket.new(s)
+      ssl.sync_close = true
+      ssl.close
+      assert(s.closed?)
+    }
+  end
+
   private
 
   def start_server_version(version, ctx_proc=nil, server_proc=nil, &blk)