Cyptography pr 20566 rebase (#25560)

Make pyca/cryptography the preferred backend for cryptographic needs (mainly vault) falling back to pycrypto

pyca/cryptography is already implicitly a dependency in many cases
through paramiko (2.0+) as well as the new openssl_publickey module,
which requires pyOpenSSL 16.0+. Additionally, pyca/cryptography is
an optional dep for better performance with vault already.

This commit leverages cryptography's padding, constant time comparisons,
and CBC/CTR modes to reduce the amount of code ansible needs to
maintain.

* Handle wrong password given for VaultAES format

* Do not display deprecation warning for cryptography on python-2.6

* Namespace all of the pycrypto imports and always import them

  Makes unittests better and the code less likely to get stupid mistakes
  (like using HMAC from cryptogrpahy when the one from pycrypto is needed)

* Add back in atfork since we need pycrypto to reinitialize its RNG just in case we're being used with old paramiko

* contrib/inventory/gce: Remove spurious require on pycrypto

(cherry picked from commit 9e16b9db275263b3ea8d1b124966fdebfc9ab271)

* Add cryptography to ec2_win_password module requirements
  * Fix python3 bug which would pass text strings to a function which
    requires byte strings.

* Attempt to add pycrypto version to setup deps

* Change hacking README for dual pycrypto/cryptography

* update dependencies for various CI scripts

* additional CI dockerfile/script updates

* add paramiko to the windows and sanity requirement set

  This is needed because ansible lists it as a requirement. Previously
  the missing dep wasn't enforced, but cryptography imports pkg_resources
  so you can't ignore a requirement any more

* Add integration test cases for old vault and for wrong passwords

* helper script for manual testing of pycrypto/cryptography

* Skip the pycrypto tests so that users without it installed can still run the unittests

* Run unittests for vault with both cryptography and pycrypto backend

25 files changed, 456 insertions, 242 deletions

diff --git a/CHANGELOG.md b/CHANGELOG.md
index 6dcfc46921..5a616c10ca 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -68,6 +68,8 @@ Ansible Changes By Release
 * Experimentally added pmrun become method.
 * Enable the docker connection plugin to use su as a become method
 * Add an encoding parameter for the replace module so that it can operate on non-utf-8 files
+* By default, Ansible now uses the cryptography module to implement vault
+  instead of the older pycrypto module.
 
 #### New Callbacks:
 - profile_roles
@@ -92,6 +94,7 @@ Ansible Changes By Release
 
 - The docker_container module has gained a new option, working_dir which allows
   specifying the working directory for the command being run in the image.
+- The ec2_win_password module now requires the cryptography python module be installed to run
 
 ### New Modules
 
diff --git a/contrib/inventory/gce.py b/contrib/inventory/gce.py
index f46a0d8a4e..076e69c5ad 100755
--- a/contrib/inventory/gce.py
+++ b/contrib/inventory/gce.py
@@ -74,7 +74,6 @@ Contributors: Matt Hite <mhite@hotmail.com>, Tom Melendez <supertom@google.com>
 Version: 0.0.3
 '''
 
-__requires__ = ['pycrypto>=2.6']
 try:
     import pkg_resources
 except ImportError:
diff --git a/hacking/README.md b/hacking/README.md
index b65bcd0b66..90f6a60151 100644
--- a/hacking/README.md
+++ b/hacking/README.md
@@ -17,7 +17,7 @@ and do not wish to install them from your operating system package manager, you
 can install them from pip
 
     $ easy_install pip               # if pip is not already available
-    $ pip install pyyaml jinja2 nose pytest passlib pycrypto
+    $ pip install -r requirements.txt
 
 From there, follow ansible instructions on docs.ansible.com as normal.
 
diff --git a/lib/ansible/executor/process/worker.py b/lib/ansible/executor/process/worker.py
index 5cb16648b1..b8c7a5b981 100644
--- a/lib/ansible/executor/process/worker.py
+++ b/lib/ansible/executor/process/worker.py
@@ -26,13 +26,15 @@ import traceback
 
 from jinja2.exceptions import TemplateNotFound
 
-# TODO: not needed if we use the cryptography library with its default RNG
-# engine
-HAS_ATFORK = True
+HAS_PYCRYPTO_ATFORK = False
 try:
     from Crypto.Random import atfork
-except ImportError:
-    HAS_ATFORK = False
+    HAS_PYCRYPTO_ATFORK = True
+except:
+    # We only need to call atfork if pycrypto is used because it will need to
+    # reinitialize its RNG.  Since old paramiko could be using pycrypto, we
+    # need to take charge of calling it.
+    pass
 
 from ansible.errors import AnsibleConnectionFailure
 from ansible.executor.task_executor import TaskExecutor
@@ -99,7 +101,7 @@ class WorkerProcess(multiprocessing.Process):
         # pr = cProfile.Profile()
         # pr.enable()
 
-        if HAS_ATFORK:
+        if HAS_PYCRYPTO_ATFORK:
             atfork()
 
         try:
diff --git a/lib/ansible/modules/cloud/amazon/ec2_win_password.py b/lib/ansible/modules/cloud/amazon/ec2_win_password.py
index cc64b4e338..af60d97d6d 100644
--- a/lib/ansible/modules/cloud/amazon/ec2_win_password.py
+++ b/lib/ansible/modules/cloud/amazon/ec2_win_password.py
@@ -60,6 +60,13 @@ options:
 extends_documentation_fragment:
     - aws
     - ec2
+
+requirements:
+    - cryptography
+
+notes:
+    - As of Ansible 2.4, this module requires the python cryptography module rather than the
+      older pycrypto module.
 '''
 
 EXAMPLES = '''
@@ -95,9 +102,11 @@ tasks:
 '''
 
 from base64 import b64decode
-from Crypto.Cipher import PKCS1_v1_5
-from Crypto.PublicKey import RSA
+from os.path import expanduser
 import datetime
+from cryptography.hazmat.backends import default_backend
+from cryptography.hazmat.primitives.asymmetric.padding import PKCS1v15
+from cryptography.hazmat.primitives.serialization import load_pem_private_key
 
 try:
     import boto.ec2
@@ -105,6 +114,9 @@ try:
 except ImportError:
     HAS_BOTO = False
 
+BACKEND = default_backend()
+
+
 def main():
     argument_spec = ec2_argument_spec()
     argument_spec.update(dict(
@@ -122,7 +134,7 @@ def main():
 
     instance_id = module.params.get('instance_id')
     key_file = module.params.get('key_file')
-    key_passphrase = module.params.get('key_passphrase')
+    b_key_passphrase = to_bytes(module.params.get('key_passphrase'), errors='surrogate_or_strict')
     wait = module.params.get('wait')
     wait_timeout = int(module.params.get('wait_timeout'))
 
@@ -147,21 +159,18 @@ def main():
         module.fail_json(msg = "wait for password timeout after %d seconds" % wait_timeout)
 
     try:
-        f = open(key_file, 'r')
+        f = open(key_file, 'rb')
     except IOError as e:
         module.fail_json(msg = "I/O error (%d) opening key file: %s" % (e.errno, e.strerror))
     else:
         try:
             with f:
-                key = RSA.importKey(f.read(), key_passphrase)
-        except (ValueError, IndexError, TypeError) as e:
+                key = load_pem_private_key(f.read(), b_key_passphrase, BACKEND)
+        except (ValueError, TypeError) as e:
             module.fail_json(msg = "unable to parse key file")
 
-    cipher = PKCS1_v1_5.new(key)
-    sentinel = 'password decryption failed!!!'
-
     try:
-        decrypted = cipher.decrypt(decoded, sentinel)
+        decrypted = key.decrypt(decoded, PKCS1v15())
     except ValueError as e:
         decrypted = None
 
diff --git a/lib/ansible/parsing/vault/__init__.py b/lib/ansible/parsing/vault/__init__.py
index 9ae68c946c..e281df3384 100644
--- a/lib/ansible/parsing/vault/__init__.py
+++ b/lib/ansible/parsing/vault/__init__.py
@@ -1,6 +1,6 @@
 # (c) 2014, James Tanner <tanner.jc@gmail.com>
 # (c) 2016, Adrian Likins <alikins@redhat.com>
-# (c) 2016, Toshio Kuratomi <tkuratomi@ansible.com>
+# (c) 2016 Toshio Kuratomi <tkuratomi@ansible.com>
 #
 # Ansible is free software: you can redistribute it and/or modify
 # it under the terms of the GNU General Public License as published by
@@ -20,47 +20,56 @@ from __future__ import (absolute_import, division, print_function)
 __metaclass__ = type
 
 import os
+import random
 import shlex
 import shutil
 import sys
 import tempfile
-import random
-from io import BytesIO
-from subprocess import call
-from hashlib import sha256
+import warnings
 from binascii import hexlify
 from binascii import unhexlify
 from hashlib import md5
+from hashlib import sha256
+from io import BytesIO
+from subprocess import call
 
-# Note: Only used for loading obsolete VaultAES files.  All files are written
-# using the newer VaultAES256 which does not require md5
-
+HAS_CRYPTOGRAPHY = False
+HAS_PYCRYPTO = False
+HAS_SOME_PYCRYPTO = False
+CRYPTOGRAPHY_BACKEND = None
 try:
-    from Crypto.Hash import SHA256, HMAC
-    HAS_HASH = True
+    with warnings.catch_warnings():
+        warnings.simplefilter("ignore", DeprecationWarning)
+        from cryptography.exceptions import InvalidSignature
+    from cryptography.hazmat.backends import default_backend
+    from cryptography.hazmat.primitives import hashes, padding
+    from cryptography.hazmat.primitives.hmac import HMAC
+    from cryptography.hazmat.primitives.kdf.pbkdf2 import PBKDF2HMAC
+    from cryptography.hazmat.primitives.ciphers import (
+        Cipher as C_Cipher, algorithms, modes
+    )
+    CRYPTOGRAPHY_BACKEND = default_backend()
+    HAS_CRYPTOGRAPHY = True
 except ImportError:
-    HAS_HASH = False
+    pass
 
-# Counter import fails for 2.0.1, requires >= 2.6.1 from pip
 try:
-    from Crypto.Util import Counter
-    HAS_COUNTER = True
-except ImportError:
-    HAS_COUNTER = False
+    from Crypto.Cipher import AES as AES_pycrypto
+    HAS_SOME_PYCRYPTO = True
 
-# KDF import fails for 2.0.1, requires >= 2.6.1 from pip
-try:
-    from Crypto.Protocol.KDF import PBKDF2
-    HAS_PBKDF2 = True
-except ImportError:
-    HAS_PBKDF2 = False
+    # Note: Only used for loading obsolete VaultAES files.  All files are written
+    # using the newer VaultAES256 which does not require md5
+    from Crypto.Hash import SHA256 as SHA256_pycrypto
+    from Crypto.Hash import HMAC as HMAC_pycrypto
 
-# AES IMPORTS
-try:
-    from Crypto.Cipher import AES as AES
-    HAS_AES = True
+    # Counter import fails for 2.0.1, requires >= 2.6.1 from pip
+    from Crypto.Util import Counter as Counter_pycrypto
+
+    # KDF import fails for 2.0.1, requires >= 2.6.1 from pip
+    from Crypto.Protocol.KDF import PBKDF2 as PBKDF2_pycrypto
+    HAS_PYCRYPTO = True
 except ImportError:
-    HAS_AES = False
+    pass
 
 from ansible.errors import AnsibleError
 from ansible.module_utils.six import PY3, binary_type
@@ -73,25 +82,6 @@ except ImportError:
     from ansible.utils.display import Display
     display = Display()
 
-# OpenSSL pbkdf2_hmac
-HAS_PBKDF2HMAC = False
-try:
-    from cryptography.hazmat.primitives.hashes import SHA256 as c_SHA256
-    from cryptography.hazmat.primitives.kdf.pbkdf2 import PBKDF2HMAC
-    from cryptography.hazmat.backends import default_backend
-    HAS_PBKDF2HMAC = True
-except ImportError:
-    pass
-except Exception as e:
-    display.vvvv("Optional dependency 'cryptography' raised an exception, falling back to 'Crypto'.")
-    import traceback
-    display.vvvv("Traceback from import of cryptography was {0}".format(traceback.format_exc()))
-
-HAS_ANY_PBKDF2HMAC = HAS_PBKDF2 or HAS_PBKDF2HMAC
-
-
-CRYPTO_UPGRADE = "ansible-vault requires a newer version of pycrypto than the one installed on your platform." \
-    " You may fix this with OS-specific commands such as: yum install python-devel; rpm -e --nodeps python-crypto; pip install pycrypto"
 
 b_HEADER = b'$ANSIBLE_VAULT'
 CIPHER_WHITELIST = frozenset((u'AES', u'AES256'))
@@ -99,11 +89,10 @@ CIPHER_WRITE_WHITELIST = frozenset((u'AES256',))
 # See also CIPHER_MAPPING at the bottom of the file which maps cipher strings
 # (used in VaultFile header) to a cipher class
 
-
-def check_prereqs():
-
-    if not HAS_AES or not HAS_COUNTER or not HAS_ANY_PBKDF2HMAC or not HAS_HASH:
-        raise AnsibleError(CRYPTO_UPGRADE)
+NEED_CRYPTO_LIBRARY = "ansible-vault requires either the cryptography library (preferred) or"
+if HAS_SOME_PYCRYPTO:
+    NEED_CRYPTO_LIBRARY += " a newer version of"
+NEED_CRYPTO_LIBRARY += " pycrypto in order to function."
 
 
 class AnsibleVaultError(AnsibleError):
@@ -411,7 +400,6 @@ class VaultEditor:
         return real_path
 
     def encrypt_bytes(self, b_plaintext):
-        check_prereqs()
 
         b_ciphertext = self.vault.encrypt(b_plaintext)
 
@@ -419,8 +407,6 @@ class VaultEditor:
 
     def encrypt_file(self, filename, output_file=None):
 
-        check_prereqs()
-
         # A file to be encrypted into a vaultfile could be any encoding
         # so treat the contents as a byte string.
 
@@ -433,8 +419,6 @@ class VaultEditor:
 
     def decrypt_file(self, filename, output_file=None):
 
-        check_prereqs()
-
         # follow the symlink
         filename = self._real_path(filename)
 
@@ -449,8 +433,6 @@ class VaultEditor:
     def create_file(self, filename):
         """ create a new encrypted file """
 
-        check_prereqs()
-
         # FIXME: If we can raise an error here, we can probably just make it
         # behave like edit instead.
         if os.path.isfile(filename):
@@ -460,8 +442,6 @@ class VaultEditor:
 
     def edit_file(self, filename):
 
-        check_prereqs()
-
         # follow the symlink
         filename = self._real_path(filename)
 
@@ -480,7 +460,6 @@ class VaultEditor:
 
     def plaintext(self, filename):
 
-        check_prereqs()
         ciphertext = self.read_data(filename)
 
         try:
@@ -492,8 +471,6 @@ class VaultEditor:
 
     def rekey_file(self, filename, b_new_password):
 
-        check_prereqs()
-
         # follow the symlink
         filename = self._real_path(filename)
 
@@ -609,10 +586,11 @@ class VaultAES:
     # Note: strings in this class should be byte strings by default.
 
     def __init__(self):
-        if not HAS_AES:
-            raise AnsibleError(CRYPTO_UPGRADE)
+        if not HAS_CRYPTOGRAPHY and not HAS_PYCRYPTO:
+            raise AnsibleError(NEED_CRYPTO_LIBRARY)
 
-    def _aes_derive_key_and_iv(self, b_password, b_salt, key_length, iv_length):
+    @staticmethod
+    def _aes_derive_key_and_iv(b_password, b_salt, key_length, iv_length):
 
         """ Create a key and an initialization vector """
 
@@ -627,37 +605,49 @@ class VaultAES:
 
         return b_key, b_iv
 
-    def encrypt(self, b_plaintext, b_password, key_length=32):
+    @staticmethod
+    def encrypt(b_plaintext, b_password, key_length=32):
 
         """ Read plaintext data from in_file and write encrypted to out_file """
 
         raise AnsibleError("Encryption disabled for deprecated VaultAES class")
 
-    def decrypt(self, b_vaulttext, b_password, key_length=32):
+    @classmethod
+    def _decrypt_cryptography(cls, b_salt, b_ciphertext, b_password, key_length):
+        bs = algorithms.AES.block_size // 8
+        b_key, b_iv = cls._aes_derive_key_and_iv(b_password, b_salt, key_length, bs)
+        cipher = C_Cipher(algorithms.AES(b_key), modes.CBC(b_iv), CRYPTOGRAPHY_BACKEND).decryptor()
+        unpadder = padding.PKCS7(algorithms.AES.block_size).unpadder()
 
-        """ Decrypt the given data and return it
-        :arg b_data: A byte string containing the encrypted data
-        :arg b_password: A byte string containing the encryption password
-        :arg key_length: Length of the key
-        :returns: A byte string containing the decrypted data
-        """
+        try:
+            b_plaintext = unpadder.update(
+                cipher.update(b_ciphertext) + cipher.finalize()
+            ) + unpadder.finalize()
+        except ValueError:
+            # In VaultAES, ValueError: invalid padding bytes can mean bad
+            # password was given
+            raise AnsibleError("Decryption failed")
 
-        display.deprecated(u'The VaultAES format is insecure and has been '
-                           'deprecated since Ansible-1.5.  Use vault rekey FILENAME to '
-                           'switch to the newer VaultAES256 format', version='2.3')
-        # http://stackoverflow.com/a/14989032
+        # split out sha and verify decryption
+        b_split_data = b_plaintext.split(b"\n", 1)
+        b_this_sha = b_split_data[0]
+        b_plaintext = b_split_data[1]
+        b_test_sha = to_bytes(sha256(b_plaintext).hexdigest())
 
-        b_ciphertext = unhexlify(b_vaulttext)
+        if b_this_sha != b_test_sha:
+            raise AnsibleError("Decryption failed")
 
+        return b_plaintext
+
+    @classmethod
+    def _decrypt_pycrypto(cls, b_salt, b_ciphertext, b_password, key_length):
         in_file = BytesIO(b_ciphertext)
         in_file.seek(0)
         out_file = BytesIO()
 
-        bs = AES.block_size
-        b_tmpsalt = in_file.read(bs)
-        b_salt = b_tmpsalt[len(b'Salted__'):]
-        b_key, b_iv = self._aes_derive_key_and_iv(b_password, b_salt, key_length, bs)
-        cipher = AES.new(b_key, AES.MODE_CBC, b_iv)
+        bs = AES_pycrypto.block_size
+        b_key, b_iv = cls._aes_derive_key_and_iv(b_password, b_salt, key_length, bs)
+        cipher = AES_pycrypto.new(b_key, AES_pycrypto.MODE_CBC, b_iv)
         b_next_chunk = b''
         finished = False
 
@@ -691,6 +681,34 @@ class VaultAES:
 
         return b_plaintext
 
+    @classmethod
+    def decrypt(cls, b_vaulttext, b_password, key_length=32):
+
+        """ Decrypt the given data and return it
+        :arg b_data: A byte string containing the encrypted data
+        :arg b_password: A byte string containing the encryption password
+        :arg key_length: Length of the key
+        :returns: A byte string containing the decrypted data
+        """
+
+        display.deprecated(u'The VaultAES format is insecure and has been '
+                           'deprecated since Ansible-1.5.  Use vault rekey FILENAME to '
+                           'switch to the newer VaultAES256 format', version='2.3')
+        # http://stackoverflow.com/a/14989032
+
+        b_vaultdata = unhexlify(b_vaulttext)
+        b_salt = b_vaultdata[len(b'Salted__'):16]
+        b_ciphertext = b_vaultdata[16:]
+
+        if HAS_CRYPTOGRAPHY:
+            b_plaintext = cls._decrypt_cryptography(b_salt, b_ciphertext, b_password, key_length)
+        elif HAS_PYCRYPTO:
+            b_plaintext = cls._decrypt_pycrypto(b_salt, b_ciphertext, b_password, key_length)
+        else:
+            raise AnsibleError(NEED_CRYPTO_LIBRARY + ' (Late detection)')
+
+        return b_plaintext
+
 
 class VaultAES256:
 
@@ -704,53 +722,79 @@ class VaultAES256:
     # Note: strings in this class should be byte strings by default.
 
     def __init__(self):
+        if not HAS_CRYPTOGRAPHY and not HAS_PYCRYPTO:
+            raise AnsibleError(NEED_CRYPTO_LIBRARY)
 
-        check_prereqs()
+    @staticmethod
+    def _create_key_cryptography(b_password, b_salt, key_length, iv_length):
+        kdf = PBKDF2HMAC(
+            algorithm=hashes.SHA256(),
+            length=2 * key_length + iv_length,
+            salt=b_salt,
+            iterations=10000,
+            backend=CRYPTOGRAPHY_BACKEND)
+        b_derivedkey = kdf.derive(b_password)
+
+        return b_derivedkey
 
     @staticmethod
-    def _create_key(b_password, b_salt, keylength, ivlength):
-        hash_function = SHA256
+    def _pbkdf2_prf(p, s):
+        hash_function = SHA256_pycrypto
+        return HMAC_pycrypto.new(p, s, hash_function).digest()
+
+    @classmethod
+    def _create_key_pycrypto(cls, b_password, b_salt, key_length, iv_length):
 
         # make two keys and one iv
-        def pbkdf2_prf(p, s):
-            return HMAC.new(p, s, hash_function).digest()
 
-        b_derivedkey = PBKDF2(b_password, b_salt, dkLen=(2 * keylength) + ivlength,
-                              count=10000, prf=pbkdf2_prf)
+        b_derivedkey = PBKDF2_pycrypto(b_password, b_salt, dkLen=(2 * key_length) + iv_length,
+                                       count=10000, prf=cls._pbkdf2_prf)
         return b_derivedkey
 
     @classmethod
     def _gen_key_initctr(cls, b_password, b_salt):
         # 16 for AES 128, 32 for AES256
-        keylength = 32
-
-        # match the size used for counter.new to avoid extra work
-        ivlength = 16
-
-        if HAS_PBKDF2HMAC:
-            backend = default_backend()
-            kdf = PBKDF2HMAC(
-                algorithm=c_SHA256(),
-                length=2 * keylength + ivlength,
-                salt=b_salt,
-                iterations=10000,
-                backend=backend)
-            b_derivedkey = kdf.derive(b_password)
+        key_length = 32
+
+        if HAS_CRYPTOGRAPHY:
+            # AES is a 128-bit block cipher, so IVs and counter nonces are 16 bytes
+            iv_length = algorithms.AES.block_size // 8
+
+            b_derivedkey = cls._create_key_cryptography(b_password, b_salt, key_length, iv_length)
+            b_iv = b_derivedkey[(key_length * 2):(key_length * 2) + iv_length]
+        elif HAS_PYCRYPTO:
+            # match the size used for counter.new to avoid extra work
+            iv_length = 16
+
+            b_derivedkey = cls._create_key_pycrypto(b_password, b_salt, key_length, iv_length)
+            b_iv = hexlify(b_derivedkey[(key_length * 2):(key_length * 2) + iv_length])
         else:
-            b_derivedkey = cls._create_key(b_password, b_salt, keylength, ivlength)
+            raise AnsibleError(NEED_CRYPTO_LIBRARY + '(Detected in initctr)')
 
-        b_key1 = b_derivedkey[:keylength]
-        b_key2 = b_derivedkey[keylength:(keylength * 2)]
-        b_iv = b_derivedkey[(keylength * 2):(keylength * 2) + ivlength]
+        b_key1 = b_derivedkey[:key_length]
+        b_key2 = b_derivedkey[key_length:(key_length * 2)]
 
-        return b_key1, b_key2, hexlify(b_iv)
+        return b_key1, b_key2, b_iv
 
-    def encrypt(self, b_plaintext, b_password):
-        b_salt = os.urandom(32)
-        b_key1, b_key2, b_iv = self._gen_key_initctr(b_password, b_salt)
+    @staticmethod
+    def _encrypt_cryptography(b_plaintext, b_salt, b_key1, b_key2, b_iv):
+        cipher = C_Cipher(algorithms.AES(b_key1), modes.CTR(b_iv), CRYPTOGRAPHY_BACKEND)
+        encryptor = cipher.encryptor()
+        padder = padding.PKCS7(algorithms.AES.block_size).padder()
+        b_ciphertext = encryptor.update(padder.update(b_plaintext) + padder.finalize())
+        b_ciphertext += encryptor.finalize()
+
+        # COMBINE SALT, DIGEST AND DATA
+        hmac = HMAC(b_key2, hashes.SHA256(), CRYPTOGRAPHY_BACKEND)
+        hmac.update(b_ciphertext)
+        b_hmac = hmac.finalize()
+
+        return hexlify(b_hmac), hexlify(b_ciphertext)
 
+    @staticmethod
+    def _encrypt_pycrypto(b_plaintext, b_salt, b_key1, b_key2, b_iv):
         # PKCS#7 PAD DATA http://tools.ietf.org/html/rfc5652#section-6.3
-        bs = AES.block_size
+        bs = AES_pycrypto.block_size
         padding_length = (bs - len(b_plaintext) % bs) or bs
         b_plaintext += to_bytes(padding_length * chr(padding_length), encoding='ascii', errors='strict')
 
@@ -758,50 +802,58 @@ class VaultAES256:
         # 1) nbits (integer) - Length of the counter, in bits.
         # 2) initial_value (integer) - initial value of the counter. "iv" from _gen_key_initctr
 
-        ctr = Counter.new(128, initial_value=int(b_iv, 16))
+        ctr = Counter_pycrypto.new(128, initial_value=int(b_iv, 16))
 
         # AES.new PARAMETERS
         # 1) AES key, must be either 16, 24, or 32 bytes long -- "key" from _gen_key_initctr
         # 2) MODE_CTR, is the recommended mode
         # 3) counter=<CounterObject>
 
-        cipher = AES.new(b_key1, AES.MODE_CTR, counter=ctr)
+        cipher = AES_pycrypto.new(b_key1, AES_pycrypto.MODE_CTR, counter=ctr)
 
         # ENCRYPT PADDED DATA
         b_ciphertext = cipher.encrypt(b_plaintext)
 
         # COMBINE SALT, DIGEST AND DATA
-        hmac = HMAC.new(b_key2, b_ciphertext, SHA256)
-        b_vaulttext = b'\n'.join([hexlify(b_salt), to_bytes(hmac.hexdigest()), hexlify(b_ciphertext)])
+        hmac = HMAC_pycrypto.new(b_key2, b_ciphertext, SHA256_pycrypto)
+
+        return to_bytes(hmac.hexdigest(), errors='surrogate_or_strict'), hexlify(b_ciphertext)
+
+    @classmethod
+    def encrypt(cls, b_plaintext, b_password):
+        b_salt = os.urandom(32)
+        b_key1, b_key2, b_iv = cls._gen_key_initctr(b_password, b_salt)
+
+        if HAS_CRYPTOGRAPHY:
+            b_hmac, b_ciphertext = cls._encrypt_cryptography(b_plaintext, b_salt, b_key1, b_key2, b_iv)
+        elif HAS_PYCRYPTO:
+            b_hmac, b_ciphertext = cls._encrypt_pycrypto(b_plaintext, b_salt, b_key1, b_key2, b_iv)
+        else:
+            raise AnsibleError(NEED_CRYPTO_LIBRARY + '(Detected in encrypt)')
+
+        b_vaulttext = b'\n'.join([hexlify(b_salt), b_hmac, b_ciphertext])
+        # Unnecessary but getting rid of it is a backwards incompatible vault
+        # format change
         b_vaulttext = hexlify(b_vaulttext)
         return b_vaulttext
 
-    def decrypt(self, b_vaulttext, b_password):
-        # SPLIT SALT, DIGEST, AND DATA
-        b_vaulttext = unhexlify(b_vaulttext)
-        b_salt, b_cryptedHmac, b_ciphertext = b_vaulttext.split(b"\n", 2)
-        b_salt = unhexlify(b_salt)
-        b_ciphertext = unhexlify(b_ciphertext)
-        b_key1, b_key2, b_iv = self._gen_key_initctr(b_password, b_salt)
-
+    @staticmethod
+    def _decrypt_cryptography(b_ciphertext, b_crypted_hmac, b_key1, b_key2, b_iv):
         # EXIT EARLY IF DIGEST DOESN'T MATCH
-        hmacDecrypt = HMAC.new(b_key2, b_ciphertext, SHA256)
-        if not self._is_equal(b_cryptedHmac, to_bytes(hmacDecrypt.hexdigest())):
+        hmac = HMAC(b_key2, hashes.SHA256(), CRYPTOGRAPHY_BACKEND)
+        hmac.update(b_ciphertext)
+        try:
+            hmac.verify(unhexlify(b_crypted_hmac))
+        except InvalidSignature:
             return None
-        # SET THE COUNTER AND THE CIPHER
-        ctr = Counter.new(128, initial_value=int(b_iv, 16))
-        cipher = AES.new(b_key1, AES.MODE_CTR, counter=ctr)
-
-        # DECRYPT PADDED DATA
-        b_plaintext = cipher.decrypt(b_ciphertext)
 
-        # UNPAD DATA
-        if PY3:
-            padding_length = b_plaintext[-1]
-        else:
-            padding_length = ord(b_plaintext[-1])
+        cipher = C_Cipher(algorithms.AES(b_key1), modes.CTR(b_iv), CRYPTOGRAPHY_BACKEND)
+        decryptor = cipher.decryptor()
+        unpadder = padding.PKCS7(128).unpadder()
+        b_plaintext = unpadder.update(
+            decryptor.update(b_ciphertext) + decryptor.finalize()
+        ) + unpadder.finalize()
 
-        b_plaintext = b_plaintext[:-padding_length]
         return b_plaintext
 
     @staticmethod
@@ -828,6 +880,46 @@ class VaultAES256:
                 result |= ord(b_x) ^ ord(b_y)
         return result == 0
 
+    @classmethod
+    def _decrypt_pycrypto(cls, b_ciphertext, b_crypted_hmac, b_key1, b_key2, b_iv):
+        # EXIT EARLY IF DIGEST DOESN'T MATCH
+        hmac_decrypt = HMAC_pycrypto.new(b_key2, b_ciphertext, SHA256_pycrypto)
+        if not cls._is_equal(b_crypted_hmac, to_bytes(hmac_decrypt.hexdigest())):
+            return None
+
+        # SET THE COUNTER AND THE CIPHER
+        ctr = Counter_pycrypto.new(128, initial_value=int(b_iv, 16))
+        cipher = AES_pycrypto.new(b_key1, AES_pycrypto.MODE_CTR, counter=ctr)
+
+        # DECRYPT PADDED DATA
+        b_plaintext = cipher.decrypt(b_ciphertext)
+
+        # UNPAD DATA
+        if PY3:
+            padding_length = b_plaintext[-1]
+        else:
+            padding_length = ord(b_plaintext[-1])
+
+        b_plaintext = b_plaintext[:-padding_length]
+        return b_plaintext
+
+    @classmethod
+    def decrypt(cls, b_vaulttext, b_password):
+        # SPLIT SALT, DIGEST, AND DATA
+        b_vaulttext = unhexlify(b_vaulttext)
+        b_salt, b_crypted_hmac, b_ciphertext = b_vaulttext.split(b"\n", 2)
+        b_salt = unhexlify(b_salt)
+        b_ciphertext = unhexlify(b_ciphertext)
+        b_key1, b_key2, b_iv = cls._gen_key_initctr(b_password, b_salt)
+
+        if HAS_CRYPTOGRAPHY:
+            b_plaintext = cls._decrypt_cryptography(b_ciphertext, b_crypted_hmac, b_key1, b_key2, b_iv)
+        elif HAS_PYCRYPTO:
+            b_plaintext = cls._decrypt_pycrypto(b_ciphertext, b_crypted_hmac, b_key1, b_key2, b_iv)
+        else:
+            raise AnsibleError(NEED_CRYPTO_LIBRARY + '(Detected in decrypt)')
+
+        return b_plaintext
 
 # Keys could be made bytes later if the code that gets the data is more
 # naturally byte-oriented
diff --git a/requirements.txt b/requirements.txt
index af13958738..09ba9fc6f0 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -6,5 +6,5 @@
 jinja2
 PyYAML
 paramiko
-pycrypto >= 2.6
+cryptography
 setuptools
diff --git a/setup.py b/setup.py
index ffa2ead709..fc369cb7cc 100644
--- a/setup.py
+++ b/setup.py
@@ -25,6 +25,10 @@ with open('requirements.txt') as requirements_file:
 # knows about
 crypto_backend = os.environ.get('ANSIBLE_CRYPTO_BACKEND', None)
 if crypto_backend:
+    if crypto_backend.strip() == 'pycrypto':
+        # Attempt to set version requirements
+        crypto_backend = 'pycrypto >= 2.6'
+
     install_requirements = [r for r in install_requirements if not (r.lower().startswith('pycrypto') or r.lower().startswith('cryptography'))]
     install_requirements.append(crypto_backend)
 
diff --git a/test/integration/targets/vault/format_1_0_AES.yml b/test/integration/targets/vault/format_1_0_AES.yml
new file mode 100644
index 0000000000..f71ddf10ce
--- /dev/null
+++ b/test/integration/targets/vault/format_1_0_AES.yml
@@ -0,0 +1,4 @@
+$ANSIBLE_VAULT;1.0;AES
+53616c7465645f5fd0026926a2d415a28a2622116273fbc90e377225c12a347e1daf4456d36a77f9
+9ad98d59f61d06a4b66718d855f16fb7bdfe54d1ec8aeaa4d06c2dc1fa630ae1846a029877f0eeb1
+83c62ffb04c2512995e815de4b4d29ed
diff --git a/test/integration/targets/vault/format_1_1_AES.yml b/test/integration/targets/vault/format_1_1_AES.yml
new file mode 100644
index 0000000000..488eceb3d0
--- /dev/null
+++ b/test/integration/targets/vault/format_1_1_AES.yml
@@ -0,0 +1,4 @@
+$ANSIBLE_VAULT;1.1;AES
+53616c7465645f5fc107ce1ef4d7b455e038a13b053225776458052f8f8f332d554809d3f150bfa3
+fe3db930508b65e0ff5947e4386b79af8ab094017629590ef6ba486814cf70f8e4ab0ed0c7d2587e
+786a5a15efeb787e1958cbdd480d076c
diff --git a/test/integration/targets/vault/format_1_1_AES256.yml b/test/integration/targets/vault/format_1_1_AES256.yml
new file mode 100644
index 0000000000..5616605e0d
--- /dev/null
+++ b/test/integration/targets/vault/format_1_1_AES256.yml
@@ -0,0 +1,6 @@
+$ANSIBLE_VAULT;1.1;AES256
+33613463343938323434396164663236376438313435633837336438366530666431643031333734
+6463646538393331333239393363333830613039376562360a396635393636636539346332336364
+35303039353164386461326439346165656463383137663932323930666632326263636266656461
+3232663537653637640a643166666232633936636664376435316664656631633166323237356163
+6138
diff --git a/test/integration/targets/vault/runme.sh b/test/integration/targets/vault/runme.sh
index 8b32720296..c06e50788e 100755
--- a/test/integration/targets/vault/runme.sh
+++ b/test/integration/targets/vault/runme.sh
@@ -11,6 +11,33 @@ echo "This is a test file" > "${TEST_FILE}"
 
 TEST_FILE_OUTPUT="${MYTMPDIR}/test_file_output"
 
+# old format
+ansible-vault view "$@" --vault-password-file vault-password-ansible format_1_0_AES.yml
+
+ansible-vault view "$@" --vault-password-file vault-password-ansible format_1_1_AES.yml
+
+# old format, wrong password
+echo "The wrong password tests are expected to return 1"
+ansible-vault view "$@" --vault-password-file vault-password-wrong format_1_0_AES.yml && :
+WRONG_RC=$?
+echo "rc was $WRONG_RC (1 is expected)"
+[ $WRONG_RC -eq 1 ]
+
+ansible-vault view "$@" --vault-password-file vault-password-wrong format_1_1_AES.yml && :
+WRONG_RC=$?
+echo "rc was $WRONG_RC (1 is expected)"
+[ $WRONG_RC -eq 1 ]
+
+ansible-vault view "$@" --vault-password-file vault-password-wrong format_1_1_AES256.yml && :
+WRONG_RC=$?
+echo "rc was $WRONG_RC (1 is expected)"
+[ $WRONG_RC -eq 1 ]
+
+set -eux
+
+# new format, view
+ansible-vault view "$@" --vault-password-file vault-password format_1_1_AES256.yml
+
 # encrypt it
 ansible-vault encrypt "$@" --vault-password-file vault-password "${TEST_FILE}"
 
diff --git a/test/integration/targets/vault/runme_change_pip_installed.sh b/test/integration/targets/vault/runme_change_pip_installed.sh
new file mode 100755
index 0000000000..986b68ed04
--- /dev/null
+++ b/test/integration/targets/vault/runme_change_pip_installed.sh
@@ -0,0 +1,27 @@
+#!/bin/bash
+
+# start by removing pycrypto and cryptography
+
+pip uninstall -y cryptography
+pip uninstall -y pycrypto
+
+./runme.sh
+
+# now just pycrypto
+pip install --user pycrypto
+
+./runme.sh
+
+
+# now just cryptography
+
+pip uninstall -y pycrypto
+pip install --user cryptography
+
+./runme.sh
+
+# now both
+
+pip install --user pycrypto
+
+./runme.sh
diff --git a/test/integration/targets/vault/vault-password-ansible b/test/integration/targets/vault/vault-password-ansible
new file mode 100644
index 0000000000..90d40550bc
--- /dev/null
+++ b/test/integration/targets/vault/vault-password-ansible
@@ -0,0 +1 @@
+ansible
diff --git a/test/integration/targets/vault/vault-password-wrong b/test/integration/targets/vault/vault-password-wrong
new file mode 100644
index 0000000000..50e2efad52
--- /dev/null
+++ b/test/integration/targets/vault/vault-password-wrong
@@ -0,0 +1 @@
+hunter42
diff --git a/test/runner/requirements/constraints.txt b/test/runner/requirements/constraints.txt
index 76a6156cc0..d525d83e11 100644
--- a/test/runner/requirements/constraints.txt
+++ b/test/runner/requirements/constraints.txt
@@ -3,3 +3,4 @@ pywinrm >= 0.2.1 # 0.1.1 required, but 0.2.1 provides better performance
 pylint >= 1.5.3, < 1.7.0 # 1.4.1 adds JSON output, but 1.5.3 fixes bugs related to JSON output
 sphinx < 1.6 ; python_version < '2.7' # sphinx 1.6 and later require python 2.7 or later
 isort < 4.2.8 # 4.2.8 changes import sort order requirements which breaks previously passing pylint tests
+pycrypto >= 2.6 # Need features found in 2.6 and greater
diff --git a/test/runner/requirements/integration.txt b/test/runner/requirements/integration.txt
index 478d15a13b..08a4cea39a 100644
--- a/test/runner/requirements/integration.txt
+++ b/test/runner/requirements/integration.txt
@@ -1,3 +1,4 @@
+cryptography
 jinja2
 jmespath
 junit-xml
diff --git a/test/runner/requirements/network-integration.txt b/test/runner/requirements/network-integration.txt
index 5fa9cf8826..846d3ede9b 100644
--- a/test/runner/requirements/network-integration.txt
+++ b/test/runner/requirements/network-integration.txt
@@ -1,5 +1,5 @@
+cryptography
 jinja2
 junit-xml
 paramiko
-pycrypto
 pyyaml
diff --git a/test/runner/requirements/sanity.txt b/test/runner/requirements/sanity.txt
index 98a92117c6..adfeb47017 100644
--- a/test/runner/requirements/sanity.txt
+++ b/test/runner/requirements/sanity.txt
@@ -1,6 +1,8 @@
+cryptography
 jinja2
 mock
 pep8
+paramiko
 pylint
 pytest
 rstcheck
diff --git a/test/runner/requirements/units.txt b/test/runner/requirements/units.txt
index 9a43516b1c..a064c2d271 100644
--- a/test/runner/requirements/units.txt
+++ b/test/runner/requirements/units.txt
@@ -1,11 +1,12 @@
 boto
 boto3
 placebo
+cryptography
+pycrypto
 jinja2
 mock
 nose
 passlib
-pycrypto
 pytest
 pytest-mock
 pytest-xdist
diff --git a/test/runner/requirements/windows-integration.txt b/test/runner/requirements/windows-integration.txt
index d6fcc566fc..df57d2a673 100644
--- a/test/runner/requirements/windows-integration.txt
+++ b/test/runner/requirements/windows-integration.txt
@@ -1,4 +1,6 @@
+cryptography
 jinja2
 junit-xml
+paramiko
 pywinrm
 pyyaml
diff --git a/test/units/parsing/vault/test_vault.py b/test/units/parsing/vault/test_vault.py
index e4a25f0a16..c657e82936 100644
--- a/test/units/parsing/vault/test_vault.py
+++ b/test/units/parsing/vault/test_vault.py
@@ -26,7 +26,7 @@ import io
 import os
 
 from binascii import hexlify
-from nose.plugins.skip import SkipTest
+import pytest
 
 from ansible.compat.tests import unittest
 
@@ -37,28 +37,6 @@ from ansible.parsing.vault import VaultLib
 from ansible.parsing import vault
 
 
-# Counter import fails for 2.0.1, requires >= 2.6.1 from pip
-try:
-    from Crypto.Util import Counter
-    HAS_COUNTER = True
-except ImportError:
-    HAS_COUNTER = False
-
-# KDF import fails for 2.0.1, requires >= 2.6.1 from pip
-try:
-    from Crypto.Protocol.KDF import PBKDF2
-    HAS_PBKDF2 = True
-except ImportError:
-    HAS_PBKDF2 = False
-
-# AES IMPORTS
-try:
-    from Crypto.Cipher import AES as AES
-    HAS_AES = True
-except ImportError:
-    HAS_AES = False
-
-
 class TestVaultIsEncrypted(unittest.TestCase):
     def test_bytes_not_encrypted(self):
         b_data = b"foobar"
@@ -151,6 +129,8 @@ class TestVaultIsEncryptedFile(unittest.TestCase):
         self.assertTrue(vault.is_encrypted_file(b_data_fo, start_pos=4, count=vault_length))
 
 
+@pytest.mark.skipif(not vault.HAS_CRYPTOGRAPHY,
+                    reason="Skipping cryptography tests because cryptography is not installed")
 class TestVaultCipherAes256(unittest.TestCase):
     def setUp(self):
         self.vault_cipher = vault.VaultAES256()
@@ -159,26 +139,71 @@ class TestVaultCipherAes256(unittest.TestCase):
         self.assertIsInstance(self.vault_cipher, vault.VaultAES256)
 
     # TODO: tag these as slow tests
-    def test_create_key(self):
+    def test_create_key_cryptography(self):
         b_password = b'hunter42'
         b_salt = os.urandom(32)
-        b_key = self.vault_cipher._create_key(b_password, b_salt, keylength=32, ivlength=16)
-        self.assertIsInstance(b_key, six.binary_type)
+        b_key_cryptography = self.vault_cipher._create_key_cryptography(b_password, b_salt, key_length=32, iv_length=16)
+        self.assertIsInstance(b_key_cryptography, six.binary_type)
+
+    @pytest.mark.skipif(not vault.HAS_PYCRYPTO, reason='Not testing pycrypto key as pycrypto is not installed')
+    def test_create_key_pycrypto(self):
+        b_password = b'hunter42'
+        b_salt = os.urandom(32)
+
+        b_key_pycrypto = self.vault_cipher._create_key_pycrypto(b_password, b_salt, key_length=32, iv_length=16)
+        self.assertIsInstance(b_key_pycrypto, six.binary_type)
+
+    @pytest.mark.skipif(not vault.HAS_PYCRYPTO,
+                        reason='Not comparing cryptography key to pycrypto key as pycrypto is not installed')
+    def test_compare_new_keys(self):
+        b_password = b'hunter42'
+        b_salt = os.urandom(32)
+        b_key_cryptography = self.vault_cipher._create_key_cryptography(b_password, b_salt, key_length=32, iv_length=16)
+
+        b_key_pycrypto = self.vault_cipher._create_key_pycrypto(b_password, b_salt, key_length=32, iv_length=16)
+        self.assertEqual(b_key_cryptography, b_key_pycrypto)
+
+    def test_create_key_known_cryptography(self):
+        b_password = b'hunter42'
+
+        # A fixed salt
+        b_salt = b'q' * 32  # q is the most random letter.
+        b_key_1 = self.vault_cipher._create_key_cryptography(b_password, b_salt, key_length=32, iv_length=16)
+        self.assertIsInstance(b_key_1, six.binary_type)
 
-    def test_create_key_known(self):
+        # verify we get the same answer
+        # we could potentially run a few iterations of this and time it to see if it's roughly constant time
+        #  and or that it exceeds some minimal time, but that would likely cause unreliable fails, esp in CI
+        b_key_2 = self.vault_cipher._create_key_cryptography(b_password, b_salt, key_length=32, iv_length=16)
+        self.assertIsInstance(b_key_2, six.binary_type)
+        self.assertEqual(b_key_1, b_key_2)
+
+        # And again with pycrypto
+        b_key_3 = self.vault_cipher._create_key_pycrypto(b_password, b_salt, key_length=32, iv_length=16)
+        self.assertIsInstance(b_key_3, six.binary_type)
+
+        # verify we get the same answer
+        # we could potentially run a few iterations of this and time it to see if it's roughly constant time
+        #  and or that it exceeds some minimal time, but that would likely cause unreliable fails, esp in CI
+        b_key_4 = self.vault_cipher._create_key_pycrypto(b_password, b_salt, key_length=32, iv_length=16)
+        self.assertIsInstance(b_key_4, six.binary_type)
+        self.assertEqual(b_key_3, b_key_4)
+        self.assertEqual(b_key_1, b_key_4)
+
+    def test_create_key_known_pycrypto(self):
         b_password = b'hunter42'
 
         # A fixed salt
         b_salt = b'q' * 32  # q is the most random letter.
-        b_key = self.vault_cipher._create_key(b_password, b_salt, keylength=32, ivlength=16)
-        self.assertIsInstance(b_key, six.binary_type)
+        b_key_3 = self.vault_cipher._create_key_pycrypto(b_password, b_salt, key_length=32, iv_length=16)
+        self.assertIsInstance(b_key_3, six.binary_type)
 
         # verify we get the same answer
         # we could potentially run a few iterations of this and time it to see if it's roughly constant time
         #  and or that it exceeds some minimal time, but that would likely cause unreliable fails, esp in CI
-        b_key_2 = self.vault_cipher._create_key(b_password, b_salt, keylength=32, ivlength=16)
-        self.assertIsInstance(b_key, six.binary_type)
-        self.assertEqual(b_key, b_key_2)
+        b_key_4 = self.vault_cipher._create_key_pycrypto(b_password, b_salt, key_length=32, iv_length=16)
+        self.assertIsInstance(b_key_4, six.binary_type)
+        self.assertEqual(b_key_3, b_key_4)
 
     def test_is_equal_is_equal(self):
         self.assertTrue(self.vault_cipher._is_equal(b'abcdefghijklmnopqrstuvwxyz', b'abcdefghijklmnopqrstuvwxyz'))
@@ -213,6 +238,21 @@ class TestVaultCipherAes256(unittest.TestCase):
         self.assertRaises(TypeError, self.vault_cipher._is_equal, b"blue fish", 2)
 
 
+@pytest.mark.skipif(not vault.HAS_PYCRYPTO,
+                    reason="Skipping Pycrypto tests because pycrypto is not installed")
+class TestVaultCipherAes256PyCrypto(TestVaultCipherAes256):
+    def setUp(self):
+        self.has_cryptography = vault.HAS_CRYPTOGRAPHY
+        vault.HAS_CRYPTOGRAPHY = False
+        super(TestVaultCipherAes256PyCrypto, self).setUp()
+
+    def tearDown(self):
+        vault.HAS_CRYPTOGRAPHY = self.has_cryptography
+        super(TestVaultCipherAes256PyCrypto, self).tearDown()
+
+
+@pytest.mark.skipif(not vault.HAS_CRYPTOGRAPHY,
+                    reason="Skipping cryptography tests because cryptography is not installed")
 class TestVaultLib(unittest.TestCase):
     def setUp(self):
         self.v = VaultLib('test-vault-password')
@@ -266,8 +306,6 @@ class TestVaultLib(unittest.TestCase):
         self.assertEqual(self.v.b_version, b"9.9", msg="version was not properly set")
 
     def test_encrypt_decrypt_aes(self):
-        if not HAS_AES or not HAS_COUNTER or not HAS_PBKDF2:
-            raise SkipTest
         self.v.cipher_name = u'AES'
         self.v.b_password = b'ansible'
         # AES encryption code has been removed, so this is old output for
@@ -281,8 +319,6 @@ fe3db930508b65e0ff5947e4386b79af8ab094017629590ef6ba486814cf70f8e4ab0ed0c7d2587e
         self.assertEqual(b_plaintext, b"foobar", msg="decryption failed")
 
     def test_encrypt_decrypt_aes256(self):
-        if not HAS_AES or not HAS_COUNTER or not HAS_PBKDF2:
-            raise SkipTest
         self.v.cipher_name = u'AES256'
         plaintext = u"foobar"
         b_vaulttext = self.v.encrypt(plaintext)
@@ -291,8 +327,6 @@ fe3db930508b65e0ff5947e4386b79af8ab094017629590ef6ba486814cf70f8e4ab0ed0c7d2587e
         self.assertEqual(b_plaintext, b"foobar", msg="decryption failed")
 
     def test_encrypt_decrypt_aes256_existing_vault(self):
-        if not HAS_AES or not HAS_COUNTER or not HAS_PBKDF2:
-            raise SkipTest
         self.v.cipher_name = u'AES256'
         b_orig_plaintext = b"Setec Astronomy"
         vaulttext = u'''$ANSIBLE_VAULT;1.1;AES256
@@ -309,12 +343,10 @@ fe3db930508b65e0ff5947e4386b79af8ab094017629590ef6ba486814cf70f8e4ab0ed0c7d2587e
         b_plaintext = self.v.decrypt(b_vaulttext)
         self.assertEqual(b_plaintext, b_orig_plaintext, msg="decryption failed")
 
+    # FIXME This test isn't working quite yet.
+    @pytest.mark.skip(reason='This test is not ready yet')
     def test_encrypt_decrypt_aes256_bad_hmac(self):
-        # FIXME This test isn't working quite yet.
-        raise SkipTest
 
-        if not HAS_AES or not HAS_COUNTER or not HAS_PBKDF2:
-            raise SkipTest
         self.v.cipher_name = 'AES256'
         # plaintext = "Setec Astronomy"
         enc_data = '''$ANSIBLE_VAULT;1.1;AES256
@@ -349,8 +381,6 @@ fe3db930508b65e0ff5947e4386b79af8ab094017629590ef6ba486814cf70f8e4ab0ed0c7d2587e
         self.v.decrypt(b_invalid_ciphertext)
 
     def test_encrypt_encrypted(self):
-        if not HAS_AES or not HAS_COUNTER or not HAS_PBKDF2:
-            raise SkipTest
         self.v.cipher_name = u'AES'
         b_vaulttext = b"$ANSIBLE_VAULT;9.9;TEST\n%s" % hexlify(b"ansible")
         vaulttext = to_text(b_vaulttext, errors='strict')
@@ -358,8 +388,6 @@ fe3db930508b65e0ff5947e4386b79af8ab094017629590ef6ba486814cf70f8e4ab0ed0c7d2587e
         self.assertRaises(errors.AnsibleError, self.v.encrypt, vaulttext)
 
     def test_decrypt_decrypted(self):
-        if not HAS_AES or not HAS_COUNTER or not HAS_PBKDF2:
-            raise SkipTest
         plaintext = u"ansible"
         self.assertRaises(errors.AnsibleError, self.v.decrypt, plaintext)
 
@@ -367,9 +395,19 @@ fe3db930508b65e0ff5947e4386b79af8ab094017629590ef6ba486814cf70f8e4ab0ed0c7d2587e
         self.assertRaises(errors.AnsibleError, self.v.decrypt, b_plaintext)
 
     def test_cipher_not_set(self):
-        # not setting the cipher should default to AES256
-        if not HAS_AES or not HAS_COUNTER or not HAS_PBKDF2:
-            raise SkipTest
         plaintext = u"ansible"
         self.v.encrypt(plaintext)
         self.assertEquals(self.v.cipher_name, "AES256")
+
+
+@pytest.mark.skipif(not vault.HAS_PYCRYPTO,
+                    reason="Skipping Pycrypto tests because pycrypto is not installed")
+class TestVaultLibPyCrypto(TestVaultLib):
+    def setUp(self):
+        self.has_cryptography = vault.HAS_CRYPTOGRAPHY
+        vault.HAS_CRYPTOGRAPHY = False
+        super(TestVaultLibPyCrypto, self).setUp()
+
+    def tearDown(self):
+        vault.HAS_CRYPTOGRAPHY = self.has_cryptography
+        super(TestVaultLibPyCrypto, self).tearDown()
diff --git a/test/units/parsing/vault/test_vault_editor.py b/test/units/parsing/vault/test_vault_editor.py
index ed609df4fb..e216b67a54 100644
--- a/test/units/parsing/vault/test_vault_editor.py
+++ b/test/units/parsing/vault/test_vault_editor.py
@@ -22,7 +22,8 @@ __metaclass__ = type
 
 import os
 import tempfile
-from nose.plugins.skip import SkipTest
+
+import pytest
 
 from ansible.compat.tests import unittest
 from ansible.compat.tests.mock import patch
@@ -32,27 +33,6 @@ from ansible.parsing import vault
 from ansible.module_utils._text import to_bytes, to_text
 
 
-# Counter import fails for 2.0.1, requires >= 2.6.1 from pip
-try:
-    from Crypto.Util import Counter
-    HAS_COUNTER = True
-except ImportError:
-    HAS_COUNTER = False
-
-# KDF import fails for 2.0.1, requires >= 2.6.1 from pip
-try:
-    from Crypto.Protocol.KDF import PBKDF2
-    HAS_PBKDF2 = True
-except ImportError:
-    HAS_PBKDF2 = False
-
-# AES IMPORTS
-try:
-    from Crypto.Cipher import AES as AES
-    HAS_AES = True
-except ImportError:
-    HAS_AES = False
-
 v10_data = """$ANSIBLE_VAULT;1.0;AES
 53616c7465645f5fd0026926a2d415a28a2622116273fbc90e377225c12a347e1daf4456d36a77f9
 9ad98d59f61d06a4b66718d855f16fb7bdfe54d1ec8aeaa4d06c2dc1fa630ae1846a029877f0eeb1
@@ -66,6 +46,8 @@ v11_data = """$ANSIBLE_VAULT;1.1;AES256
 3739"""
 
 
+@pytest.mark.skipif(not vault.HAS_CRYPTOGRAPHY,
+                    reason="Skipping cryptography tests because cryptography is not installed")
 class TestVaultEditor(unittest.TestCase):
 
     def setUp(self):
@@ -423,9 +405,6 @@ class TestVaultEditor(unittest.TestCase):
 
     def test_decrypt_1_0(self):
         # Skip testing decrypting 1.0 files if we don't have access to AES, KDF or Counter.
-        if not HAS_AES or not HAS_COUNTER or not HAS_PBKDF2:
-            raise SkipTest
-
         v10_file = tempfile.NamedTemporaryFile(delete=False)
         with v10_file as f:
             f.write(to_bytes(v10_data))
@@ -451,9 +430,6 @@ class TestVaultEditor(unittest.TestCase):
         assert fdata.strip() == "foo", "incorrect decryption of 1.0 file: %s" % fdata.strip()
 
     def test_decrypt_1_1(self):
-        if not HAS_AES or not HAS_COUNTER or not HAS_PBKDF2:
-            raise SkipTest
-
         v11_file = tempfile.NamedTemporaryFile(delete=False)
         with v11_file as f:
             f.write(to_bytes(v11_data))
@@ -478,10 +454,6 @@ class TestVaultEditor(unittest.TestCase):
         assert fdata.strip() == "foo", "incorrect decryption of 1.0 file: %s" % fdata.strip()
 
     def test_rekey_migration(self):
-        # Skip testing rekeying files if we don't have access to AES, KDF or Counter.
-        if not HAS_AES or not HAS_COUNTER or not HAS_PBKDF2:
-            raise SkipTest
-
         v10_file = tempfile.NamedTemporaryFile(delete=False)
         with v10_file as f:
             f.write(to_bytes(v10_data))
@@ -542,3 +514,16 @@ class TestVaultEditor(unittest.TestCase):
 
         res = ve._real_path(file_link_path)
         self.assertEqual(res, file_path)
+
+
+@pytest.mark.skipif(not vault.HAS_PYCRYPTO,
+                    reason="Skipping pycrypto tests because pycrypto is not installed")
+class TestVaultEditorPyCrypto(unittest.TestCase):
+    def setUp(self):
+        self.has_cryptography = vault.HAS_CRYPTOGRAPHY
+        vault.HAS_CRYPTOGRAPHY = False
+        super(TestVaultEditorPyCrypto, self).setUp()
+
+    def tearDown(self):
+        vault.HAS_CRYPTOGRAPHY = self.has_cryptography
+        super(TestVaultEditorPyCrypto, self).tearDown()
diff --git a/test/utils/shippable/other.sh b/test/utils/shippable/other.sh
index d42d671851..5c436077ad 100755
--- a/test/utils/shippable/other.sh
+++ b/test/utils/shippable/other.sh
@@ -5,6 +5,10 @@ set -o pipefail
 retry.py apt-get update -qq
 retry.py apt-get install -qq \
     shellcheck \
+    libssl-dev \
+    libffi-dev \
+
+pip install cryptography
 
 retry.py pip install tox --disable-pip-version-check
 
diff --git a/test/utils/tox/requirements.txt b/test/utils/tox/requirements.txt
index 03a3013690..ca3dd4fe93 100644
--- a/test/utils/tox/requirements.txt
+++ b/test/utils/tox/requirements.txt
@@ -11,6 +11,7 @@ unittest2
 redis
 python-memcached
 python-systemd
+cryptography
 pycrypto
 botocore
 boto3