How to "do cryptography" in Python, and on iOS and Android.
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Cryptography example

How to "do encryption" using cryptographic primitives. Inspired by Cryptographic Right Answers by Colin Percival.

Requirements and Installation

  • You need Python 2.x, and this is cross-platform, i.e. works on Windows, Max OS X, and Linux.

  • You will require PyCrypto. If you're on Windows, here are the binaries.

  • If you want to run the tests (recommended) you need nose. You can install nose via pip. In order to install both pip and nose one could, for example, run (with cygwin on Windows):

    curl | python
    curl | python
    pip install nose

How to use

>>> from utilities import crypto
>>> plaintext = "this is some text"
>>> key = "this is my key"
>>> ciphertext = crypto.encrypt_string(plaintext, key)
>>> plaintext_after = crypto.decrypt_string(ciphertext, key)
>>> print plaintext_after
this is some text

What happens if someone alters the encrypted string? You'll get one of two exceptions:

>>> ciphertext_altered = ciphertext[:-1] + '\0'
>>> plaintext_after = crypto.decrypt_string(ciphertext_altered, key)
Traceback (most recent call last):
  File "<pyshell#14>", line 1, in <module>
    plaintext_after = crypto.decrypt_string(ciphertext_altered, key)
  File ".\utilities\", line 76, in decrypt_string
    decrypt_file(ciphertext_obj, key, plaintext_obj)
  File ".\utilities\", line 172, in decrypt_file
    raise HMACIsNotValidException


>>> ciphertext_truncated = ciphertext[:-5]
>>> plaintext_after = crypto.decrypt_string(ciphertext_truncated, key)
Traceback (most recent call last):
  File "<pyshell#16>", line 1, in <module>
    plaintext_after = crypto.decrypt_string(ciphertext_truncated, key)
  File ".\utilities\", line 76, in decrypt_string
    decrypt_file(ciphertext_obj, key, plaintext_obj)
  File ".\utilities\", line 168, in decrypt_file
    raise InvalidFormatException("len(hmac) %s != hmac_size %s" % (len(hmac), hmac_size))
InvalidFormatException: 'len(hmac) 27 != hmac_size 32'

You can do streaming symmetric encryption and decryption of files, such that very large files do not get fully loaded into memory:

>>> plaintext_filepath = "c:\file1.txt"
>>> ciphertext_filepath = "C:\file2.txt"
>>> key = "my little key"
... with open(plaintext_filepath, "rb") as f_in:
...     with open(ciphertext_filepath, "rb+") as f_out:
...         crypto.encrypt_file(f_in,
...                             key,
...                             f_out)
>>> plaintext_after_filepath = "c:\file3.txt"
>>> with open(ciphertext_filepath, "rb") as f_in:
...     with open(plaintext_after_filepath, "wb") as f_out:
...         crypto.decrypt_file(f_in,
...                             key,
...                             f_out)

And by adding a compress flag you can compress plaintext before encryption for both strings and files:

>>> plaintext = "X" * 1024 * 1024
>>> key = "my little key"
>>> ciphertext = crypto.encrypt_string(plaintext, key, compress=True)
>>> print len(ciphertext)


As stated in Cryptographic Right Answers:

  • Encrypting data: Use AES in CTR (Counter) mode, and append an HMAC.
  • AES key length: Use 256-bit AES keys.
  • Hash / HMAC algorithm: Use SHA256 / HMAC-SHA256.
  • Password handling: As soon as you receive a password, hash it using scrypt or PBKDF2 and erase the plaintext password from memory.

Following from this, the process for encrypting a file is:

  • Generate password_salt, a random 16-byte string.
  • Using PBKDF2, derive cipher_password_derived from the key and password_salt. This will be used to encrypt the plaintext.
  • Generate nonce, a random 8-byte string concatenated with a counter that starts at 0.
  • Start a new AES cipher instance in counter (CTR) mode that uses the nonce and counter above, with cipher_password_derived as the key.
  • Generate hmac_salt, a random 16-byte string.
  • Using PBKDF2, derive hmac_password_derived from the key and hmac_salt. This will be used to generate the HMAC.
  • Start a new HMAC instance which hashes all values used, not just the ciphertext that will eventually be generated, using hmac_password_derived.
  • Read in the plaintext in chunks from the file-like object. If we're compressing then stream this into a BZ2Compressor() instance. Write this into the ciphertext file.

and the process for decrypting a file (decrypt_file()):

  • Unpack the start of the encrypted file to get configuration values (pbkdf2_count, pbkdf2_dk_len, compress) and public values (password_salt, nonce, hmac_salt).
  • Prepare the HMAC with the configuration values and public values.
  • First pass: stream in the ciphertext into the HMAC object. If the HMAC isn't valid, bail out.
  • Use PBKDF2 to derive the password.
  • Create an AES instance in CTR mode using the derived password.
  • Second pass: stream in the ciphertext. If we're compressing then decompress as well. Write this to the ciphertext file.

the file format of an encrypted file is:

  • TODO. See, in particular header_format in encrypt_file().

Development notes

  • While developing I like installing watchdog and then using the following command from the root of the git repo to auto-rerun the nose unit tests:

    I:\Programming\crypto_example>watchmedo shell-command --patterns="*.py" --recursive --command="nosetests --no-skip --detailed-errors --stop --verbosity=2 --tests test/"


  • Make a unit-tested example in iOS.
  • Make a unit-tested example in Android.
  • Using Android emulators / iOS simulators / web server magic, run functional verification on the lot to prove each can talk to the other.