diff --git a/CHANGES.rst b/CHANGES.rst
index ed5e40777a..c991fd9e03 100644
--- a/CHANGES.rst
+++ b/CHANGES.rst
@@ -17,6 +17,11 @@ General
   (GITHUB-556, LIBCLOUD-728)
   [Scott Kruger]
 
+- Throw a more user-friendly exception if a client fails to establish SSL / TLS
+  connection with a server because of an unsupported SSL / TLS version.
+  (GITHUB-682)
+  [Tomaz Muraus]
+
 Compute
 ~~~~~~~
 
diff --git a/libcloud/httplib_ssl.py b/libcloud/httplib_ssl.py
index cac4098b49..5f11d05fc8 100644
--- a/libcloud/httplib_ssl.py
+++ b/libcloud/httplib_ssl.py
@@ -40,6 +40,24 @@
 
 HTTP_PROXY_ENV_VARIABLE_NAME = 'http_proxy'
 
+# Error message which is thrown when establishing SSL / TLS connection fails
+UNSUPPORTED_TLS_VERSION_ERROR_MSG = """
+Failed to establish SSL / TLS connection (%s). It is possible that the server \
+doesn't support requested SSL / TLS version (%s).
+For information on how to work around this issue, please see \
+https://libcloud.readthedocs.org/en/latest/other/\
+ssl-certificate-validation.html#changing-used-ssl-tls-version
+""".strip()
+
+# Maps ssl.PROTOCOL_* constant to the actual SSL / TLS version name
+SSL_CONSTANT_TO_TLS_VERSION_MAP = {
+    0: 'SSL v2',
+    2: 'SSLv3, TLS v1.0, TLS v1.1, TLS v1.2',
+    3: 'TLS v1.0',
+    4: 'TLS v1.1',
+    5: 'TLS v1.2'
+}
+
 
 class LibcloudBaseConnection(object):
     """
@@ -272,12 +290,40 @@ def connect(self):
         if self.http_proxy_used:
             self._activate_http_proxy(sock=sock)
 
-        self.sock = ssl.wrap_socket(sock,
-                                    self.key_file,
-                                    self.cert_file,
-                                    cert_reqs=ssl.CERT_REQUIRED,
-                                    ca_certs=self.ca_cert,
-                                    ssl_version=libcloud.security.SSL_VERSION)
+        try:
+            self.sock = ssl.wrap_socket(
+                sock,
+                self.key_file,
+                self.cert_file,
+                cert_reqs=ssl.CERT_REQUIRED,
+                ca_certs=self.ca_cert,
+                ssl_version=libcloud.security.SSL_VERSION)
+        except socket.error:
+            exc = sys.exc_info()[1]
+            exc_msg = str(exc)
+
+            # Re-throw an exception with a more friendly error message
+            if 'connection reset by peer' in exc_msg.lower():
+                ssl_version = libcloud.security.SSL_VERSION
+                ssl_version = SSL_CONSTANT_TO_TLS_VERSION_MAP[ssl_version]
+                msg = (UNSUPPORTED_TLS_VERSION_ERROR_MSG %
+                       (exc_msg, ssl_version))
+
+                # Note: In some cases arguments are (errno, message) and in
+                # other it's just (message,)
+                exc_args = getattr(exc, 'args', [])
+
+                if len(exc_args) == 2:
+                    new_exc_args = [exc.args[0], msg]
+                else:
+                    new_exc_args = [msg]
+
+                new_exc = socket.error(*new_exc_args)
+                new_exc.original_exc = exc
+                raise new_exc
+
+            raise exc
+
         cert = self.sock.getpeercert()
         try:
             match_hostname(cert, self.host)
diff --git a/libcloud/test/test_httplib_ssl.py b/libcloud/test/test_httplib_ssl.py
index 65e676c9d9..28eed69bbe 100644
--- a/libcloud/test/test_httplib_ssl.py
+++ b/libcloud/test/test_httplib_ssl.py
@@ -16,7 +16,9 @@
 import os
 import sys
 import os.path
+import socket
 
+import mock
 from mock import patch
 
 import libcloud.security
@@ -105,6 +107,41 @@ def test_setup_ca_cert(self, _):
         self.assertRaisesRegexp(RuntimeError, expected_msg,
                                 self.httplib_object._setup_ca_cert)
 
+    @mock.patch('socket.create_connection', mock.MagicMock())
+    @mock.patch('socket.socket', mock.MagicMock())
+    @mock.patch('ssl.wrap_socket')
+    def test_connect_throws_friendly_error_message_on_ssl_wrap_connection_reset_by_peer(self, mock_wrap_socket):
+        # Test that we re-throw a more friendly error message in case
+        # "connection reset by peer" error occurs when trying to establish a
+        # SSL connection
+        libcloud.security.VERIFY_SSL_CERT = True
+        self.httplib_object.verify = True
+        self.httplib_object.http_proxy_used = False
+
+        # No connection reset by peer, original exception should be thrown
+        mock_wrap_socket.side_effect = Exception('foo bar fail')
+
+        expected_msg = 'foo bar fail'
+        self.assertRaisesRegexp(Exception, expected_msg,
+                                self.httplib_object.connect)
+
+        # Connection reset by peer, wrapped exception with friendly error
+        # message should be thrown
+        mock_wrap_socket.side_effect = socket.error('Connection reset by peer')
+
+        expected_msg = 'Failed to establish SSL / TLS connection'
+        self.assertRaisesRegexp(socket.error, expected_msg,
+                                self.httplib_object.connect)
+
+        # Same error but including errno
+        with self.assertRaises(socket.error) as cm:
+            mock_wrap_socket.side_effect = socket.error(104, 'Connection reset by peer')
+            self.httplib_object.connect()
+
+        e = cm.exception
+        self.assertEqual(e.errno, 104)
+        self.assertTrue(expected_msg in str(e))
+
 
 if __name__ == '__main__':
     sys.exit(unittest.main())