AngstromCTF2019: Classy Cipher

The Challenge

Classy Cipher Crypto 20 > Every CTF starts off with a Caesar cipher, but we’re more classy.
Author: defund
link: https://files.actf.co/2e1940179916e0501fbba0de705a668e42646c916276d7a51ad6a2d2cc381720/classy_cipher.py

The linked file is a simple python script.

from secret import flag, shift

def encrypt(d, s):
    e = ''
    for c in d:
        e += chr((ord(c)+s) % 0xff)
    return e

assert encrypt(flag, shift) == ':<M?TLH8<A:KFBG@V'

The Solution

The python script rotates characters by an unknown amount. The character rotation must be less than 255 (the ASCII range) as enforced by % 0xff in the encrypt() function.

The rotation can be calculated because the first 4 values of the flag are known:

:<M? must be actf

The easiest way to calculate the shift is using the encrypt() algorithm to compare the known characters.

def shift_test(have, want):
    for x in range(255):
        tested = encrypt(want, x)
        if tested == have:
            return x

After calculating the rotation, a lookup table can be created for all ascii values and used to decipher the ciphertext

def generate_table(shift):
    table = {}
    # generate all ascii chars
    for x in range(255):
        # get the key and its cipher equivalent
        key = chr(x)
        cipheredKey = encrypt(key,shift)
        # add to table
        table[cipheredKey] = key
    return table

def decipher(ciphertext, shift):
    lookup = generate_table(shift)
    out = ''
    for char in ciphertext:
        out += lookup[char]
    return out

Combining the above scripts reveals the flag:

The rotation was 216
The flag is actf{so_charming}

Here is the script I used, commented for clarity

#from secret import flag, shift
def encrypt(d, s):
e = ''
for c in d:
e += chr((ord©+s) % 0xff)
return e
#assert encrypt(flag, shift) == ':<M?TLH8<A:KFBG@V'
# test for the correct shift
def shift_test(have, want):
for x in range(255):
tested = encrypt(want, x)
if tested == have:
return x
def generate_table(shift):
table = {}
# generate all ascii chars
for x in range(255):
# get the key and its cipher equivalent
key = chr(x)
cipheredKey = encrypt(key,shift)
# add to table
table[cipheredKey] = key
return table
def decipher(ciphertext, shift):
lookup = generate_table(shift)
out = ''
for char in ciphertext:
out += lookup[char]
return out
# algorithm starts here
# we know the flag
ciphertext = ':<M?TLH8<A:KFBG@V'
# test for the shift used to get the known part of the flag
shift = shift_test(have=':<M?', want='actf')
print(f'Shift is: {shift}')
# generate a lookup table and print the flag
flag = decipher(ciphertext, shift)
print(f"The flag says: {flag}")