def test_cbc_padding_oracle():
# Set 3, challenge 17 CBC Padding Oracle
path_to_test_data = os.path.join(
os.path.dirname(os.path.abspath(__file__)), "data/17.txt")
with open(path_to_test_data, "r") as f:
plaintexts = f.read().split("\n")
block_size = 16
key = os.urandom(block_size)
iv = os.urandom(block_size)
plaintext = random.choice(plaintexts)
unpadded_plaintext_bytes = base64_to_bytes(plaintext)
plaintext_bytes = pkcs_7(unpadded_plaintext_bytes, block_size)
ciphertext = aes_cbc_encrypt(key, unpadded_plaintext_bytes, iv)
cbc_solver = Solver(block_size, iv, key, ciphertext)
reconstructed_bytes = cbc_solver.run(plaintext_bytes)
# Since I'm pretending as if I didn't know the IV, I'm going to compare
# only the blocks that were *not* constructed by XORing with the IV.
# As an attacker I could guess e.g. that the IV was all 0s or some other
# insecure default that might have been due to an insecure default in the
# crypto library used by the developer.
result_without_iv_based_block = "".join(
[chr(x) for x in reconstructed_bytes])
plaintext_without_iv_based_block = plaintext_bytes[
2 * cbc_solver.block_size:(cbc_solver.num_blocks - 1) *
cbc_solver.block_size].decode("utf-8")
assert plaintext_without_iv_based_block in result_without_iv_based_block
def test_break_random_access_rw_ctr():
# Set 4, challenge 25: Break "random access read/write" AES CTR
path_to_test_data = os.path.join(
os.path.dirname(os.path.abspath(__file__)), "data/20.txt")
with open(path_to_test_data, "r") as f:
plaintexts_b64 = f.readlines()
plaintexts = [base64_to_bytes(x) for x in plaintexts_b64]
key = os.urandom(BLOCK_SIZE)
nonce = 0
ciphertexts = [
aes_ctr_encrypt(key, x, nonce, BLOCK_SIZE) for x in plaintexts
]
edited_ciphertexts = []
for ciphertext in ciphertexts:
# Edit at position 0... why not!
# And we'll edit to have all null bytes as the "new" plaintext. Allowed by the API!
new_plaintext = b"\x00" * len(ciphertext)
edited_ciphertext = aes_ctr_edit(key, ciphertext, 0, new_plaintext,
nonce)
edited_ciphertexts.append(edited_ciphertext)
# This means that the "edited_ciphertexts" are really just the keystream.
for ind, ciphertext in enumerate(ciphertexts):
reconstructed_plaintext = xor(edited_ciphertexts[ind], ciphertext)
assert reconstructed_plaintext == plaintexts[ind]
def test_aes_ctr_decrypt():
# Set 3, challenge 18: Implement CTR, the stream cipher mode
ciphertext = base64_to_bytes(
"L77na/nrFsKvynd6HzOoG7GHTLXsTVu9qvY/2syLXzhPweyyMTJULu/6/kXX0KSvoOLSFQ=="
)
key = "YELLOW SUBMARINE".encode("utf-8")
nonce = 0
result = aes_ctr_decrypt(key, ciphertext, nonce, BLOCK_SIZE)
assert result == b"Yo, VIP Let's kick it Ice, Ice, baby Ice, Ice, baby "
def test_break_repeating_key_xor():
# Set 1, challenge 6 (break repeating key XOR)
path_to_data = os.path.join(
os.path.dirname(os.path.abspath(__file__)), "data/6.txt"
)
with open(path_to_data, "r") as f:
data = f.read().split("\n")
data = "".join(data)
ciphertext = base64_to_bytes(data)
key = break_repeating_key_xor(ciphertext)
assert key.decode("utf8") == "Terminator X: Bring the noise"
def test_aes_ecb_decrypt():
# Set 1, challenge 7: AES in ECB mode
path_to_data = os.path.join(os.path.dirname(os.path.abspath(__file__)),
"data/7.txt")
with open(path_to_data, "r") as f:
base64_ciphertext = f.read()
ciphertext = base64_to_bytes(base64_ciphertext)
key = "YELLOW SUBMARINE".encode("utf-8")
plaintext = aes_ecb_decrypt(key, ciphertext)
assert "Play that funky music A little louder now" in plaintext.decode(
"utf8")
def test_aes_cbc_decrypt():
# Set 2, challenge 10: Implement CBC mode
path_to_data = os.path.join(os.path.dirname(os.path.abspath(__file__)),
"data/10.txt")
with open(path_to_data, "r") as f:
base64_ciphertext = f.read()
ciphertext = base64_to_bytes(base64_ciphertext)
key = "YELLOW SUBMARINE".encode("utf-8")
iv = bytes([0]) * BLOCK_SIZE
plaintext = aes_cbc_decrypt(key, ciphertext, iv, remove_padding=False)
assert "Vanilla's on the mike, man I'm not lazy." in plaintext.decode(
"utf-8")
assert "I'm back and I'm ringin' the bell" in plaintext.decode("utf-8")
def test_break_fixed_nonce_ctr_statistically():
# Set 3, challenge 20: Break fixed-nonce CTR mode statistically
path_to_test_data = os.path.join(
os.path.dirname(os.path.abspath(__file__)), "data/20.txt")
with open(path_to_test_data, "r") as f:
plaintexts_b64 = f.readlines()
plaintexts = [base64_to_bytes(x) for x in plaintexts_b64]
key = b"aaaaaaaaaaaaaaaa"
nonce = 0 # Fixed nonce
ciphertexts = [
aes_ctr_encrypt(key, x, nonce, BLOCK_SIZE) for x in plaintexts
]
# Truncate to shortest ciphertext.
num_blocks = len(min(ciphertexts)) // BLOCK_SIZE
truncate = num_blocks * BLOCK_SIZE
truncated_ciphertexts = [x[:truncate] for x in ciphertexts]
# Generate keystream to compare the reconstructed answer with.
counter = CounterMode(key, nonce, BLOCK_SIZE)
keystream_blocks = [
counter._generate_keystream_block() for x in range(num_blocks)
]
true_keystream = b"".join(keystream_blocks)
assert truncate == len(true_keystream)
combined_ciphertext = b"".join(truncated_ciphertexts)
reconstructed_keystream = break_ctr_statistically(combined_ciphertext,
truncate)
percent_correct = (
[x == y for x, y in zip(true_keystream, reconstructed_keystream)
].count(True) / len(reconstructed_keystream) * 100)
assert percent_correct > 70.0
def test_break_fixed_nonce_ctr():
# Set 3, challenge 19: Break fixed-nonce CTR mode using substitutions
path_to_test_data = os.path.join(
os.path.dirname(os.path.abspath(__file__)), "data/19.txt")
with open(path_to_test_data, "r") as f:
plaintexts_b64 = f.readlines()
plaintexts = [base64_to_bytes(x) for x in plaintexts_b64]
key = os.urandom(BLOCK_SIZE)
nonce = 0 # Fixed nonce
ciphertexts = [
aes_ctr_encrypt(key, x, nonce, BLOCK_SIZE) for x in plaintexts
]
# Each ciphertext has been encrypted against the same keystream:
# c_1 = p_1 xor k_1
# c_2 = p_2 xor k_2
# since k_1 = k_2 = k, we can xor ciphertexts to get:
# c_1 xor c_2 = p_1 xor k xor p_2 xor k = p_1 xor p_2
C1_xor_C2 = namedtuple("C1_xor_C2", "c1_index c2_index value")
xored = []
for ind_x, ciphertext_x in enumerate(ciphertexts):
for ind_y, ciphertext_y in enumerate(ciphertexts):
if ind_x != ind_y:
result = [
bytes([x ^ y]) for x, y in zip(ciphertext_x, ciphertext_y)
]
result_bytes = b"".join(result)
result_tuple = C1_xor_C2(ind_x, ind_y, result_bytes)
xored.append(result_tuple)
xored = list(set(xored))
reconstructed_keystream = b"\x00" * 32
keystream_byte_guesses = {} # this will be a dict of lists
# Crib dragging:
# we have pairs of p_1 xor p_2
# if we xor with p_{test} = sp_1 = p, we'll get; p_1 xor p_{test} xor p_2 = p_2 only
# so let's try some trigrams and see if we get any english text, this will be p_2
common_ngrams = [
b"the ",
b" and ",
b"ing ",
b" her ",
b" his ",
b"this ",
b"And ",
b"This ",
b"The ",
b" in the ",
b" in ",
b" or ",
b"Or ",
b"What ",
b"To ",
b"When ",
b" when ",
b"All ",
b"of the ",
b" my ",
b"and th",
b"ation",
b"There ",
b" there ",
b" I ",
b" I had ",
b"Her ",
b"His ",
b" which ",
b"Which ",
b"Their ",
b" their ",
b" would ",
b"Would ",
b"end",
b"for ",
b"ate",
b"eth",
b"all",
b" said",
b" will",
b"I have ",
]
# top_words = [x.encode('utf8') for x in top_n_english_words(10)]
top_words_with_space = [(x + " ").encode("utf8")
for x in top_n_english_words(10)]
english_guesses = list(set(common_ngrams + top_words_with_space))
for pair in xored:
for test_ngram in english_guesses:
result = xor(pair.value, test_ngram)
for found_ngram in english_guesses:
if found_ngram != test_ngram and found_ngram in result:
# if the area where we found a match in c1_xor_c2 = \x00, then skip
# that's what we are doing with the found_ngram != test_ngram
# Otherwise we found a few bytes of keystream
starting_index = result.find(found_ngram)
len_ngram = len(found_ngram)
for index in range(len_ngram):
# k = p xor c
# but we don't know _which_ c to xor with
# let's add both and then vote at the end
ct_index = starting_index + index
c1 = ciphertexts[pair.c1_index]
c2 = ciphertexts[pair.c2_index]
keystream_byte_guess_c1 = bytes(
[found_ngram[index] ^ c1[ct_index]])
keystream_byte_guess_c2 = bytes(
[found_ngram[index] ^ c2[ct_index]])
try:
keystream_byte_guesses[ct_index].append(
keystream_byte_guess_c1)
keystream_byte_guesses[ct_index].append(
keystream_byte_guess_c2)
except KeyError:
keystream_byte_guesses[ct_index] = [
keystream_byte_guess_c1,
keystream_byte_guess_c2,
]
for ct_index in keystream_byte_guesses.keys():
guesses = keystream_byte_guesses[ct_index]
winning_guess = max(set(guesses), key=guesses.count)
reconstructed_keystream = (reconstructed_keystream[:ct_index] +
winning_guess +
reconstructed_keystream[ct_index + 1:])
expected_keystream = aes_ctr_encrypt(key, b"\x00" * 32, nonce, BLOCK_SIZE)
percent_correct = (
[x == y for x, y in zip(expected_keystream, reconstructed_keystream)
].count(True) / len(reconstructed_keystream) * 100)
assert percent_correct > 80.0
def test_random_prefix_byte_at_a_time_ecb_decryption():
# Set 2, challenge 14: Byte-at-a-time ECB decryption (harder)
path_to_test_data = os.path.join(
os.path.dirname(os.path.abspath(__file__)), "data/12.txt")
with open(path_to_test_data, "r") as f:
append_text_str = f.read()
append_bytes = base64_to_bytes(append_text_str)
# We won't actually use the key anywhere other than to pass it to the
# oracle function.
key = gen_random_block()
# Get random number of bytes. This we will prepend to the plaintext.
random_number_of_bytes = random.randint(1, 15)
prepend_bytes = os.urandom(random_number_of_bytes)
blocksize = 16
ciphertext = ecb_encrypt_prepend_and_append(key, b"", append_bytes,
prepend_bytes)
test_str = "A" * blocksize
ciphertext_of_all_As = aes_ecb_encrypt(
key, test_str.encode("utf-8"))[0:blocksize]
# We don't really know where to start in the ciphertext. Previously we started
# decrypting with the first ciphertext block, when we manipulated it to
# contain one target character.
# We need to first determine how much space the prefix bytes are taking up.
block_to_begin_at = None
number_of_characters_in_test_string = None
for num_of_test_characters in range(blocksize * 2 - 1, 1, -1):
test_str = "A" * num_of_test_characters
ciphertext = ecb_encrypt_prepend_and_append(key,
test_str.encode("utf-8"),
append_bytes,
prepend_bytes)
for block_num in range(1, len(ciphertext) // blocksize):
if (ciphertext_of_all_As == ciphertext[(block_num - 1) *
blocksize:block_num *
blocksize]):
block_to_begin_at = block_num
number_of_characters_in_test_string = num_of_test_characters
# We add sufficient characters in the target block so that the unknown prefix
# bytes fill a block boundary. Then we start at that block boundary and decrypt
# as before.
reconstructed_str = ""
for index_of_target_block in range(block_to_begin_at,
len(ciphertext) // blocksize):
bytes_so_far_this_block = b""
for test_byte in range(blocksize):
if index_of_target_block == block_to_begin_at:
# If it's the first block, we control the prefix bytes.
attacker_controlled_bytes = "A" * (blocksize - test_byte - 1)
# Prefix is used for the dict calculation
prefix = (attacker_controlled_bytes.encode("utf-8") +
bytes_so_far_this_block)
# Add our prefix to pad the unknown bytes to the block boundary.
attacker_controlled_bytes = (
"A" * number_of_characters_in_test_string +
attacker_controlled_bytes)
else:
# But if it's the second block or later, we need to use the
# bytes we reconstructed from the previous block as the prefix.
previous_block_bytes = reconstructed_str[-1 * (blocksize - 1):]
# The prefix is used for the dict calculation
prefix = previous_block_bytes.encode("utf-8")
# Add our prefix to pad the unknown bytes to the block boundary.
attacker_controlled_bytes = (
"A" * number_of_characters_in_test_string + "A" *
(blocksize - test_byte - 1))
ciphertext = ecb_encrypt_prepend_and_append(
key,
attacker_controlled_bytes.encode("utf-8"),
append_bytes,
prepend_bytes,
)
cipher_dict = construct_ecb_attack_dict(key, prefix)
target_block_ciphertext = ciphertext[
(index_of_target_block - 1) * blocksize:index_of_target_block *
blocksize]
last_char = cipher_dict[target_block_ciphertext]
reconstructed_str = reconstructed_str + last_char
bytes_so_far_this_block = bytes_so_far_this_block + last_char.encode(
"utf-8")
assert "With my rag-top down so my hair can blow" in reconstructed_str
def test_byte_at_a_time_ecb_decryption():
# Set 2, challenge 12: Byte-at-a-time ECB decryption (Simple)
path_to_test_data = os.path.join(
os.path.dirname(os.path.abspath(__file__)), "data/12.txt")
with open(path_to_test_data, "r") as f:
append_text_str = f.read()
append_bytes = base64_to_bytes(append_text_str)
# We won't actually use the key anywhere other than to pass it to the
# oracle function ecb_encrypt_append.
key = gen_random_block()
# Determine blocksize
previous_ciphertext_len = None
test_input = "A"
for blocksize in range(100):
test_input = "A" + test_input
test_ciphertext = ecb_encrypt_append(key, test_input.encode("utf-8"),
append_bytes)
if (previous_ciphertext_len
and len(test_ciphertext) - previous_ciphertext_len != 0):
blocksize = len(test_ciphertext) - previous_ciphertext_len
break
previous_ciphertext_len = len(test_ciphertext)
assert blocksize == BLOCK_SIZE # Check we inferred blocksize correctly.
ciphertext = ecb_encrypt_append(key, b"", append_bytes)
# Now we make repeated calls (as described in problem statement) to
# pass inputs that are (blocksize - 1) in length.
reconstructed_str = ""
for index_of_target_block in range(1, len(ciphertext) // blocksize):
bytes_so_far_this_block = b""
for test_byte in range(blocksize):
if index_of_target_block == 1:
# If it's the first block, we control the prefix bytes.
attacker_controlled_bytes = "A" * (blocksize - test_byte - 1)
# Prefix is used for the dict calculation
prefix = (attacker_controlled_bytes.encode("utf-8") +
bytes_so_far_this_block)
else:
# But if it's the second block or later, we need to use the
# bytes we reconstructed from the previous block as the prefix.
previous_block_bytes = reconstructed_str[-1 * (blocksize - 1):]
# The prefix is used for the dict calculation
prefix = previous_block_bytes.encode("utf-8")
# Attacker-controlled bytes here are just to make sure there is only
# a single unknown character in the target block.
attacker_controlled_bytes = "A" * (blocksize - test_byte - 1)
ciphertext = ecb_encrypt_append(
key, attacker_controlled_bytes.encode("utf-8"), append_bytes)
cipher_dict = construct_ecb_attack_dict(key, prefix)
target_block_ciphertext = ciphertext[
(index_of_target_block - 1) * blocksize:index_of_target_block *
blocksize]
last_char = cipher_dict[target_block_ciphertext]
reconstructed_str = reconstructed_str + last_char
bytes_so_far_this_block = bytes_so_far_this_block + last_char.encode(
"utf-8")
assert "With my rag-top down so my hair can blow" in reconstructed_str