diff --git a/Lib/ssl.py b/Lib/ssl.py
index af1cc84..a634442 100644
--- a/Lib/ssl.py
+++ b/Lib/ssl.py
@@ -122,6 +122,9 @@
         if _context:
             self.context = _context
         else:
+            if server_side and not certfile:
+                raise ValueError("certfile must be specified for server-side "
+                                 "operations")
             if certfile and not keyfile:
                 keyfile = certfile
             self.context = SSLContext(ssl_version)
@@ -138,7 +141,7 @@
             self.ssl_version = ssl_version
             self.ca_certs = ca_certs
             self.ciphers = ciphers
-
+        self.server_side = server_side
         self.do_handshake_on_connect = do_handshake_on_connect
         self.suppress_ragged_eofs = suppress_ragged_eofs
         connected = False
@@ -358,7 +361,8 @@
     def connect(self, addr):
         """Connects to remote ADDR, and then wraps the connection in
         an SSL channel."""
-
+        if self.server_side:
+            raise ValueError("can't connect in server-side mode")
         # Here we assume that the socket is client-side, and not
         # connected at the time of the call.  We connect it, then wrap it.
         if self._sslobj:
diff --git a/Lib/test/test_ssl.py b/Lib/test/test_ssl.py
index 71ba9e1..b485605 100644
--- a/Lib/test/test_ssl.py
+++ b/Lib/test/test_ssl.py
@@ -172,6 +172,19 @@
             ss = ssl.wrap_socket(s)
             self.assertEqual(timeout, ss.gettimeout())
 
+    def test_errors(self):
+        sock = socket.socket()
+        with self.assertRaisesRegexp(ValueError, "certfile must be specified"):
+            ssl.wrap_socket(sock, server_side=True)
+            ssl.wrap_socket(sock, server_side=True, certfile="")
+        s = ssl.wrap_socket(sock, server_side=True, certfile=CERTFILE)
+        self.assertRaisesRegexp(ValueError, "can't connect in server-side mode",
+                                s.connect, (HOST, 8080))
+        with self.assertRaisesRegexp(IOError, "No such file"):
+            ssl.wrap_socket(sock, certfile=WRONGCERT)
+            ssl.wrap_socket(sock, keyfile=WRONGCERT)
+            ssl.wrap_socket(sock, certfile=WRONGCERT, keyfile=WRONGCERT)
+
 
 class ContextTests(unittest.TestCase):
 
@@ -240,7 +253,7 @@
         ctx.load_cert_chain(CERTFILE)
         ctx.load_cert_chain(CERTFILE, keyfile=CERTFILE)
         self.assertRaises(TypeError, ctx.load_cert_chain, keyfile=CERTFILE)
-        with self.assertRaisesRegexp(ssl.SSLError, "system lib"):
+        with self.assertRaisesRegexp(IOError, "No such file"):
             ctx.load_cert_chain(WRONGCERT)
         with self.assertRaisesRegexp(ssl.SSLError, "PEM lib"):
             ctx.load_cert_chain(BADCERT)
@@ -270,7 +283,7 @@
         ctx.load_verify_locations(cafile=BYTES_CERTFILE, capath=None)
         self.assertRaises(TypeError, ctx.load_verify_locations)
         self.assertRaises(TypeError, ctx.load_verify_locations, None, None)
-        with self.assertRaisesRegexp(ssl.SSLError, "system lib"):
+        with self.assertRaisesRegexp(IOError, "No such file"):
             ctx.load_verify_locations(WRONGCERT)
         with self.assertRaisesRegexp(ssl.SSLError, "PEM lib"):
             ctx.load_verify_locations(BADCERT)
@@ -863,6 +876,9 @@
             except socket.error as x:
                 if support.verbose:
                     sys.stdout.write("\nsocket.error is %s\n" % x[1])
+            except IOError as x:
+                if support.verbose:
+                    sys.stdout.write("\nsocket.error is %s\n" % str(x))
             else:
                 raise AssertionError("Use of invalid cert should have failed!")
         finally: