diff --git a/Lib/ssl.py b/Lib/ssl.py
index 4f291f44869..9e88073916b 100644
--- a/Lib/ssl.py
+++ b/Lib/ssl.py
@@ -324,7 +324,9 @@ class SSLSocket(socket):
         from the socket module."""
 
         self._makefile_refs += 1
-        return _fileobject(self, mode, bufsize)
+        # close=True so as to decrement the reference count when done with
+        # the file-like object.
+        return _fileobject(self, mode, bufsize, close=True)
 
 
 
diff --git a/Lib/test/test_ssl.py b/Lib/test/test_ssl.py
index 5917b513df7..c418cd4ea85 100644
--- a/Lib/test/test_ssl.py
+++ b/Lib/test/test_ssl.py
@@ -7,7 +7,9 @@ import asyncore
 import socket
 import select
 import time
+import gc
 import os
+import errno
 import pprint
 import urllib, urlparse
 import traceback
@@ -165,6 +167,22 @@ class BasicTests(unittest.TestCase):
         del ss
         self.assertEqual(wr(), None)
 
+    def test_makefile_close(self):
+        # Issue #5238: creating a file-like object with makefile() shouldn't
+        # leak the underlying file descriptor.
+        ss = ssl.wrap_socket(socket.socket(socket.AF_INET))
+        fd = ss.fileno()
+        f = ss.makefile()
+        f.close()
+        # The fd is still open
+        os.read(fd, 0)
+        # Closing the SSL socket should close the fd too
+        ss.close()
+        gc.collect()
+        with self.assertRaises(OSError) as e:
+            os.read(fd, 0)
+        self.assertEqual(e.exception.errno, errno.EBADF)
+
 
 class NetworkedTests(unittest.TestCase):
 
diff --git a/Misc/NEWS b/Misc/NEWS
index 26ce4e051f3..580f9bf85d2 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -25,6 +25,9 @@ Core and Builtins
 Library
 -------
 
+- Issue #5238: Calling makefile() on an SSL object would prevent the
+  underlying socket from being closed until all objects get truely destroyed.
+
 - Issue #7943: Fix circular reference created when instantiating an SSL
   socket.  Initial patch by Péter Szabó.