diff --git a/glanceclient/common/http.py b/glanceclient/common/http.py
index db1acefa..11cda0ab 100644
--- a/glanceclient/common/http.py
+++ b/glanceclient/common/http.py
@@ -19,14 +19,9 @@ import logging
 import os
 import socket
 import StringIO
+import struct
 import urlparse
 
-try:
-    import ssl
-except ImportError:
-    #TODO(bcwaldon): Handle this failure more gracefully
-    pass
-
 try:
     import json
 except ImportError:
@@ -37,6 +32,7 @@ if not hasattr(urlparse, 'parse_qsl'):
     import cgi
     urlparse.parse_qsl = cgi.parse_qsl
 
+import OpenSSL
 
 from glanceclient import exc
 
@@ -82,6 +78,7 @@ class HTTPClient(object):
             _kwargs['cert_file'] = kwargs.get('cert_file', None)
             _kwargs['key_file'] = kwargs.get('key_file', None)
             _kwargs['insecure'] = kwargs.get('insecure', False)
+            _kwargs['ssl_compression'] = kwargs.get('ssl_compression', True)
 
         return _kwargs
 
@@ -204,67 +201,109 @@ class HTTPClient(object):
         return self._http_request(url, method, **kwargs)
 
 
-class VerifiedHTTPSConnection(httplib.HTTPSConnection):
-    """httplib-compatibile connection using client-side SSL authentication
-
-    :see http://code.activestate.com/recipes/
-            577548-https-httplib-client-connection-with-certificate-v/
+class OpenSSLConnectionDelegator(object):
     """
+    An OpenSSL.SSL.Connection delegator.
 
+    Supplies an additional 'makefile' method which httplib requires
+    and is not present in OpenSSL.SSL.Connection.
+
+    Note: Since it is not possible to inherit from OpenSSL.SSL.Connection
+    a delegator must be used.
+    """
+    def __init__(self, *args, **kwargs):
+        self.connection = OpenSSL.SSL.Connection(*args, **kwargs)
+
+    def __getattr__(self, name):
+        return getattr(self.connection, name)
+
+    def makefile(self, *args, **kwargs):
+        return socket._fileobject(self.connection, *args, **kwargs)
+
+
+class VerifiedHTTPSConnection(httplib.HTTPSConnection):
+    """
+    Extended HTTPSConnection which uses the OpenSSL library
+    for enhanced SSL support.
+    """
     def __init__(self, host, port, key_file=None, cert_file=None,
-                 ca_file=None, timeout=None, insecure=False):
-        httplib.HTTPSConnection.__init__(self, host, port, key_file=key_file,
+                 ca_file=None, timeout=None, insecure=False,
+                 ssl_compression=True):
+        httplib.HTTPSConnection.__init__(self, host, port,
+                                         key_file=key_file,
                                          cert_file=cert_file)
         self.key_file = key_file
         self.cert_file = cert_file
-        if ca_file is not None:
-            self.ca_file = ca_file
-        else:
-            self.ca_file = self.get_system_ca_file()
         self.timeout = timeout
         self.insecure = insecure
+        self.ssl_compression = ssl_compression
+        self.ca_file = ca_file
+        self.setcontext()
+
+    @staticmethod
+    def verify_callback(connection, x509, errnum, errdepth, preverify_ok):
+        # Pass through OpenSSL's default result
+        return preverify_ok
+
+    def setcontext(self):
+        """
+        Set up the OpenSSL context.
+        """
+        self.context = OpenSSL.SSL.Context(OpenSSL.SSL.SSLv23_METHOD)
+
+        if self.ssl_compression is False:
+            self.context.set_options(0x20000)  # SSL_OP_NO_COMPRESSION
+
+        if self.insecure is not True:
+            self.context.set_verify(OpenSSL.SSL.VERIFY_PEER,
+                                    self.verify_callback)
+        else:
+            self.context.set_verify(OpenSSL.SSL.VERIFY_NONE,
+                                    self.verify_callback)
+
+        if self.cert_file:
+            try:
+                self.context.use_certificate_file(self.cert_file)
+            except Exception, e:
+                msg = 'Unable to load cert from "%s" %s' % (self.cert_file, e)
+                raise exc.SSLConfigurationError(msg)
+            if self.key_file is None:
+                # We support having key and cert in same file
+                try:
+                    self.context.use_privatekey_file(self.cert_file)
+                except Exception, e:
+                    msg = ('No key file specified and unable to load key '
+                           'from "%s" %s' % (self.cert_file, e))
+                    raise exc.SSLConfigurationError(msg)
+
+        if self.key_file:
+            try:
+                self.context.use_privatekey_file(self.key_file)
+            except Exception, e:
+                msg = 'Unable to load key from "%s" %s' % (self.key_file, e)
+                raise exc.SSLConfigurationError(msg)
+
+        if self.ca_file:
+            try:
+                self.context.load_verify_locations(self.ca_file)
+            except Exception, e:
+                msg = 'Unable to load CA from "%s"' % (self.ca_file, e)
+                raise exc.SSLConfigurationError(msg)
+        else:
+            self.context.set_default_verify_paths()
 
     def connect(self):
         """
-        Connect to a host on a given (SSL) port.
-        If ca_file is pointing somewhere, use it to check Server Certificate.
-
-        Redefined/copied and extended from httplib.py:1105 (Python 2.6.x).
-        This is needed to pass cert_reqs=ssl.CERT_REQUIRED as parameter to
-        ssl.wrap_socket(), which forces SSL to check server certificate against
-        our client certificate.
+        Connect to an SSL port using the OpenSSL library and apply
+        per-connection parameters.
         """
-        sock = socket.create_connection((self.host, self.port), self.timeout)
-
-        if self._tunnel_host:
-            self.sock = sock
-            self._tunnel()
-
-        if self.insecure is True:
-            kwargs = {'cert_reqs': ssl.CERT_NONE}
-        else:
-            kwargs = {'cert_reqs': ssl.CERT_REQUIRED, 'ca_certs': self.ca_file}
-
-        if self.cert_file:
-            kwargs['certfile'] = self.cert_file
-            if self.key_file:
-                kwargs['keyfile'] = self.key_file
-
-        self.sock = ssl.wrap_socket(sock, **kwargs)
-
-    @staticmethod
-    def get_system_ca_file():
-        """"Return path to system default CA file"""
-        # Standard CA file locations for Debian/Ubuntu, RedHat/Fedora,
-        # Suse, FreeBSD/OpenBSD
-        ca_path = ['/etc/ssl/certs/ca-certificates.crt',
-                   '/etc/pki/tls/certs/ca-bundle.crt',
-                   '/etc/ssl/ca-bundle.pem',
-                   '/etc/ssl/cert.pem']
-        for ca in ca_path:
-            if os.path.exists(ca):
-                return ca
-        return None
+        sock = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
+        if self.timeout is not None:
+            # '0' microseconds
+            sock.setsockopt(socket.SOL_SOCKET, socket.SO_RCVTIMEO,
+                            struct.pack('LL', self.timeout, 0))
+        self.sock = OpenSSLConnectionDelegator(self.context, sock)
+        self.sock.connect((self.host, self.port))
 
 
 class ResponseBodyIterator(object):
diff --git a/glanceclient/exc.py b/glanceclient/exc.py
index 771d0e32..5559cc7f 100644
--- a/glanceclient/exc.py
+++ b/glanceclient/exc.py
@@ -164,3 +164,7 @@ class NoTokenLookupException(Exception):
 class EndpointNotFound(Exception):
     """DEPRECATED"""
     pass
+
+
+class SSLConfigurationError(BaseException):
+    pass
diff --git a/glanceclient/shell.py b/glanceclient/shell.py
index c13a7b8c..2dd473e4 100644
--- a/glanceclient/shell.py
+++ b/glanceclient/shell.py
@@ -81,6 +81,11 @@ class OpenStackImagesShell(object):
             default=600,
             help='Number of seconds to wait for a response')
 
+        parser.add_argument('--no-ssl-compression',
+            dest='ssl_compression',
+            default=True, action='store_false',
+            help='Disable SSL compression when using https.')
+
         parser.add_argument('-f', '--force',
             dest='force',
             default=False, action='store_true',
@@ -395,6 +400,7 @@ class OpenStackImagesShell(object):
             'ca_file': args.ca_file,
             'cert_file': args.cert_file,
             'key_file': args.key_file,
+            'ssl_compression': args.ssl_compression
         }
 
         client = glanceclient.Client(api_version, endpoint, **kwargs)
diff --git a/tests/test_ssl.py b/tests/test_ssl.py
new file mode 100644
index 00000000..8c6cb267
--- /dev/null
+++ b/tests/test_ssl.py
@@ -0,0 +1,112 @@
+# Copyright 2012 OpenStack LLC.
+# All Rights Reserved.
+#
+#    Licensed under the Apache License, Version 2.0 (the "License"); you may
+#    not use this file except in compliance with the License. You may obtain
+#    a copy of the License at
+#
+#         http://www.apache.org/licenses/LICENSE-2.0
+#
+#    Unless required by applicable law or agreed to in writing, software
+#    distributed under the License is distributed on an "AS IS" BASIS, WITHOUT
+#    WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied. See the
+#    License for the specific language governing permissions and limitations
+#    under the License.
+
+import os
+import unittest
+
+from glanceclient import exc
+from glanceclient.common import http
+
+TEST_VAR_DIR = os.path.abspath(os.path.join(os.path.dirname(__file__),
+                                            'var'))
+
+
+class TestVerifiedHTTPSConnection(unittest.TestCase):
+    def test_ssl_init_ok(self):
+        """
+        Test VerifiedHTTPSConnection class init
+        """
+        key_file = os.path.join(TEST_VAR_DIR, 'privatekey.key')
+        cert_file = os.path.join(TEST_VAR_DIR, 'certificate.crt')
+        ca_file = os.path.join(TEST_VAR_DIR, 'ca.crt')
+        try:
+            conn = http.VerifiedHTTPSConnection('127.0.0.1', 0,
+                                                key_file=key_file,
+                                                cert_file=cert_file,
+                                                ca_file=ca_file)
+        except exc.SSLConfigurationError:
+            self.fail('Failed to init VerifiedHTTPSConnection.')
+
+    def test_ssl_init_cert_no_key(self):
+        """
+        Test VerifiedHTTPSConnection: absense of SSL key file.
+        """
+        cert_file = os.path.join(TEST_VAR_DIR, 'certificate.crt')
+        ca_file = os.path.join(TEST_VAR_DIR, 'ca.crt')
+        try:
+            conn = http.VerifiedHTTPSConnection('127.0.0.1', 0,
+                                                cert_file=cert_file,
+                                                ca_file=ca_file)
+            self.fail('Failed to raise assertion.')
+        except exc.SSLConfigurationError:
+            pass
+
+    def test_ssl_init_key_no_cert(self):
+        """
+        Test VerifiedHTTPSConnection: absense of SSL cert file.
+        """
+        key_file = os.path.join(TEST_VAR_DIR, 'privatekey.key')
+        ca_file = os.path.join(TEST_VAR_DIR, 'ca.crt')
+        try:
+            conn = http.VerifiedHTTPSConnection('127.0.0.1', 0,
+                                                key_file=key_file,
+                                                ca_file=ca_file)
+        except:
+            self.fail('Failed to init VerifiedHTTPSConnection.')
+
+    def test_ssl_init_bad_key(self):
+        """
+        Test VerifiedHTTPSConnection: bad key.
+        """
+        key_file = os.path.join(TEST_VAR_DIR, 'badkey.key')
+        cert_file = os.path.join(TEST_VAR_DIR, 'certificate.crt')
+        ca_file = os.path.join(TEST_VAR_DIR, 'ca.crt')
+        try:
+            conn = http.VerifiedHTTPSConnection('127.0.0.1', 0,
+                                                cert_file=cert_file,
+                                                ca_file=ca_file)
+            self.fail('Failed to raise assertion.')
+        except exc.SSLConfigurationError:
+            pass
+
+    def test_ssl_init_bad_cert(self):
+        """
+        Test VerifiedHTTPSConnection: bad cert.
+        """
+        key_file = os.path.join(TEST_VAR_DIR, 'privatekey.key')
+        cert_file = os.path.join(TEST_VAR_DIR, 'badcert.crt')
+        ca_file = os.path.join(TEST_VAR_DIR, 'ca.crt')
+        try:
+            conn = http.VerifiedHTTPSConnection('127.0.0.1', 0,
+                                                cert_file=cert_file,
+                                                ca_file=ca_file)
+            self.fail('Failed to raise assertion.')
+        except exc.SSLConfigurationError:
+            pass
+
+    def test_ssl_init_bad_ca(self):
+        """
+        Test VerifiedHTTPSConnection: bad CA.
+        """
+        key_file = os.path.join(TEST_VAR_DIR, 'privatekey.key')
+        cert_file = os.path.join(TEST_VAR_DIR, 'certificate.crt')
+        ca_file = os.path.join(TEST_VAR_DIR, 'badca.crt')
+        try:
+            conn = http.VerifiedHTTPSConnection('127.0.0.1', 0,
+                                                cert_file=cert_file,
+                                                ca_file=ca_file)
+            self.fail('Failed to raise assertion.')
+        except exc.SSLConfigurationError:
+            pass
diff --git a/tests/var/ca.crt b/tests/var/ca.crt
new file mode 100644
index 00000000..9d66ca62
--- /dev/null
+++ b/tests/var/ca.crt
@@ -0,0 +1,35 @@
+-----BEGIN CERTIFICATE-----
+MIIGDDCCA/SgAwIBAgIJAPSvwQYk4qI4MA0GCSqGSIb3DQEBBQUAMGExCzAJBgNV
+BAYTAkFVMRMwEQYDVQQIEwpTb21lLVN0YXRlMRUwEwYDVQQKEwxPcGVuc3RhY2sg
+Q0ExEjAQBgNVBAsTCUdsYW5jZSBDQTESMBAGA1UEAxMJR2xhbmNlIENBMB4XDTEy
+MDIwOTE3MTAwMloXDTIyMDIwNjE3MTAwMlowYTELMAkGA1UEBhMCQVUxEzARBgNV
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+/l3EXe3/TCrbzgZ7lW3QLTCTEE2eEzwYG3wfDTOyoBq+F6ct6ADh+86gmpbIRfYI
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+WoRMgEwjGJWqzhJZUYpUAQ==
+-----END CERTIFICATE-----
diff --git a/tests/var/certificate.crt b/tests/var/certificate.crt
new file mode 100644
index 00000000..3c1aa636
--- /dev/null
+++ b/tests/var/certificate.crt
@@ -0,0 +1,30 @@
+-----BEGIN CERTIFICATE-----
+MIIFLjCCAxYCAQEwDQYJKoZIhvcNAQEFBQAwYTELMAkGA1UEBhMCQVUxEzARBgNV
+BAgTClNvbWUtU3RhdGUxFTATBgNVBAoTDE9wZW5zdGFjayBDQTESMBAGA1UECxMJ
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+YfTLnrjs7Hj6ThMGcEnfvc46dWK3dz0RjsQzUxugPuEkLA==
+-----END CERTIFICATE-----
diff --git a/tests/var/privatekey.key b/tests/var/privatekey.key
new file mode 100644
index 00000000..b63df3d2
--- /dev/null
+++ b/tests/var/privatekey.key
@@ -0,0 +1,51 @@
+-----BEGIN RSA PRIVATE KEY-----
+MIIJKAIBAAKCAgEA16VJEDeqbmr6PoM96NSuJK1XT5dZuzYzSQ8g//mR9BBjXBDe
+4moNajxOybI6hjzWbECtXTKF20s/jkovarzXiZwXH8FMeakwLcMgG/QMRpMLjGny
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++Zlhvzi7XCPfcjzqVhp6bP+Whv+uAwydg+uxZ2o+oCh1fuk1xTvCmcZZ8bYLYmQy
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+rSU7x0QMGwtb+Bv7bgLDuztMNtLtgd7vqRtOpufq5xKqfqwfYZrpEWE34BBUUbFS
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+-----END RSA PRIVATE KEY-----
diff --git a/tools/pip-requires b/tools/pip-requires
index bbb4edfa..b0db8581 100644
--- a/tools/pip-requires
+++ b/tools/pip-requires
@@ -1,4 +1,5 @@
 argparse
 prettytable>=0.6,<0.7
 python-keystoneclient>=0.1.2,<0.2
+pyOpenSSL
 warlock<2