diff --git a/Lib/test/test_smtplib.py b/Lib/test/test_smtplib.py
index df0bf4c..dab4fe0 100644
--- a/Lib/test/test_smtplib.py
+++ b/Lib/test/test_smtplib.py
@@ -11,21 +11,25 @@
 from unittest import TestCase
 from test import test_support
 
+# PORT is used to communicate the port number assigned to the server
+# to the test client
 HOST = "localhost"
-PORT = 54328
+PORT = None
 
 def server(evt, buf):
-    serv = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
-    serv.settimeout(3)
-    serv.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
-    serv.bind(("", PORT))
-    serv.listen(5)
     try:
+        serv = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
+        serv.settimeout(3)
+        serv.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
+        serv.bind(("", 0))
+        global PORT
+        PORT = serv.getsockname()[1]
+        serv.listen(5)
         conn, addr = serv.accept()
     except socket.timeout:
         pass
     else:
-        n = 200
+        n = 500
         while buf and n > 0:
             r, w, e = select.select([], [conn], [])
             if w:
@@ -38,6 +42,7 @@
         conn.close()
     finally:
         serv.close()
+        PORT = None
         evt.set()
 
 class GeneralTests(TestCase):
@@ -46,7 +51,16 @@
         self.evt = threading.Event()
         servargs = (self.evt, "220 Hola mundo\n")
         threading.Thread(target=server, args=servargs).start()
-        time.sleep(.1)
+
+        # wait until server thread has assigned a port number
+        n = 500
+        while PORT is None and n > 0:
+            time.sleep(0.01)
+            n -= 1
+
+        # wait a little longer (sometimes connections are refused
+        # on slow machines without this additional wait)
+        time.sleep(0.5)
 
     def tearDown(self):
         self.evt.wait()
@@ -69,7 +83,8 @@
 
     def testNonnumericPort(self):
         # check that non-numeric port raises ValueError
-        self.assertRaises(socket.error, smtplib.SMTP, "localhost", "bogus")
+        self.assertRaises(socket.error, smtplib.SMTP,
+                          "localhost", "bogus")
 
     def testTimeoutDefault(self):
         # default
@@ -96,61 +111,104 @@
 
 
 # Test server using smtpd.DebuggingServer
-def debugging_server(evt):
-    serv = smtpd.DebuggingServer(("", PORT), ('nowhere', -1))
+def debugging_server(serv_evt, client_evt):
+    serv = smtpd.DebuggingServer(("", 0), ('nowhere', -1))
+    global PORT
+    PORT = serv.getsockname()[1]
 
     try:
-        asyncore.loop(timeout=.01, count=300)
+        if hasattr(select, 'poll'):
+            poll_fun = asyncore.poll2
+        else:
+            poll_fun = asyncore.poll
+
+        n = 1000
+        while asyncore.socket_map and n > 0:
+            poll_fun(0.01, asyncore.socket_map)
+
+            # when the client conversation is finished, it will
+            # set client_evt, and it's then ok to kill the server
+            if client_evt.isSet():
+                serv.close()
+                break
+
+            n -= 1
+
     except socket.timeout:
         pass
     finally:
         # allow some time for the client to read the result
         time.sleep(0.5)
+        serv.close()
         asyncore.close_all()
-        evt.set()
+        PORT = None
+        time.sleep(0.5)
+        serv_evt.set()
 
 MSG_BEGIN = '---------- MESSAGE FOLLOWS ----------\n'
 MSG_END = '------------ END MESSAGE ------------\n'
 
 # Test behavior of smtpd.DebuggingServer
+# NOTE: the SMTP objects are created with a non-default local_hostname
+# argument to the constructor, since (on some systems) the FQDN lookup
+# caused by the default local_hostname sometimes takes so long that the
+# test server times out, causing the test to fail.
 class DebuggingServerTests(TestCase):
 
     def setUp(self):
+        # temporarily replace sys.stdout to capture DebuggingServer output
         self.old_stdout = sys.stdout
         self.output = StringIO.StringIO()
         sys.stdout = self.output
 
-        self.evt = threading.Event()
-        threading.Thread(target=debugging_server, args=(self.evt,)).start()
-        time.sleep(.5)
+        self.serv_evt = threading.Event()
+        self.client_evt = threading.Event()
+        serv_args = (self.serv_evt, self.client_evt)
+        threading.Thread(target=debugging_server, args=serv_args).start()
+
+        # wait until server thread has assigned a port number
+        n = 500
+        while PORT is None and n > 0:
+            time.sleep(0.01)
+            n -= 1
+
+        # wait a little longer (sometimes connections are refused
+        # on slow machines without this additional wait)
+        time.sleep(0.5)
 
     def tearDown(self):
-        self.evt.wait()
+        # indicate that the client is finished
+        self.client_evt.set()
+        # wait for the server thread to terminate
+        self.serv_evt.wait()
+        # restore sys.stdout
         sys.stdout = self.old_stdout
 
     def testBasic(self):
         # connect
-        smtp = smtplib.SMTP(HOST, PORT)
-        smtp.sock.close()
+        smtp = smtplib.SMTP(HOST, PORT, local_hostname='localhost', timeout=3)
+        smtp.quit()
 
     def testEHLO(self):
-        smtp = smtplib.SMTP(HOST, PORT)
-        self.assertEqual(smtp.ehlo(), (502, 'Error: command "EHLO" not implemented'))
-        smtp.sock.close()
+        smtp = smtplib.SMTP(HOST, PORT, local_hostname='localhost', timeout=3)
+        expected = (502, 'Error: command "EHLO" not implemented')
+        self.assertEqual(smtp.ehlo(), expected)
+        smtp.quit()
 
     def testHELP(self):
-        smtp = smtplib.SMTP(HOST, PORT)
+        smtp = smtplib.SMTP(HOST, PORT, local_hostname='localhost', timeout=3)
         self.assertEqual(smtp.help(), 'Error: command "HELP" not implemented')
-        smtp.sock.close()
+        smtp.quit()
 
     def testSend(self):
         # connect and send mail
         m = 'A test message'
-        smtp = smtplib.SMTP(HOST, PORT)
+        smtp = smtplib.SMTP(HOST, PORT, local_hostname='localhost', timeout=3)
         smtp.sendmail('John', 'Sally', m)
-        smtp.sock.close()
+        smtp.quit()
 
-        self.evt.wait()
+        self.client_evt.set()
+        self.serv_evt.wait()
         self.output.flush()
         mexpect = '%s%s\n%s' % (MSG_BEGIN, m, MSG_END)
         self.assertEqual(self.output.getvalue(), mexpect)
@@ -166,17 +224,28 @@
         self.evt = threading.Event()
         servargs = (self.evt, "199 no hello for you!\n")
         threading.Thread(target=server, args=servargs).start()
-        time.sleep(.5)
+
+        # wait until server thread has assigned a port number
+        n = 500
+        while PORT is None and n > 0:
+            time.sleep(0.01)
+            n -= 1
+
+        # wait a little longer (sometimes connections are refused
+        # on slow machines without this additional wait)
+        time.sleep(0.5)
 
     def tearDown(self):
         self.evt.wait()
         sys.stdout = self.old_stdout
 
     def testFailingHELO(self):
-        self.assertRaises(smtplib.SMTPConnectError, smtplib.SMTP, HOST, PORT)
+        self.assertRaises(smtplib.SMTPConnectError, smtplib.SMTP,
+                            HOST, PORT, 'localhost', 3)
 
 def test_main(verbose=None):
-    test_support.run_unittest(GeneralTests, DebuggingServerTests, BadHELOServerTests)
+    test_support.run_unittest(GeneralTests, DebuggingServerTests,
+                              BadHELOServerTests)
 
 if __name__ == '__main__':
     test_main()