Cryptoverse 2022 - Super Guesser

Cameron published on
7 min, 1290 words

Categories: CTF Writeup

Problem Description

Super Guesser is an easy rated reversing challenge for the Crytoverse 2022 CTF. We are given a short challenge description:

Only the true guessing king can solve this challenge.


We are provided a link to download guesser.pyc, a compiled python binary. Just to confirm there aren't any shenangins with the file extension, let's check the file type.

$ file guesser.pyc
guesser.pyc: Byte-compiled Python module for CPython 3.8, timestamp-based, .py timestamp: Sun Sep 11 18:00:05 2022 UTC, .py size: 682 bytes

The file utility tells us that we are, in fact, dealing with a compiled python binary. In this case CPython 3.8 is the version.

Note: it's important that we use the correct version of python when running the compiled .pyc file otherwise we might get a magic number error as shown below and be unable to execute the program.

$ python guesser.pyc
RuntimeError: Bad magic number in .pyc file

If your system has an incompatible version of Python, I'd recommend installing a tool like pyenv to install and manage other python versions side by side on your system.

Now let's try running this program to see what we get as output.

$ python guesser.pyc
Guess: test

$ python guesser.pyc

Okay it look's like the program is checking our input. Perhaps it is checking against the challenge's flag.

Referring to the challenge title we know that this is a reversing challenge, so the next logical step is to try decompiling the python binary. One popular python decompiler is decompyle3, which we can see from the PyPI page supports python versions 3.7+ which should work fine for the bytecode we have.

We can decompile guesser.pyc with the command:

decompyle3 guesser.pyc

This gets us the source code

# decompyle3 version 3.9.0
# Python bytecode version base 3.8.0 (3413)
# Decompiled from: Python 3.8.0 (default, Oct 29 2022, 20:02:52)
# [GCC 12.2.0]
# Embedded file name: /home/
# Compiled at: 2022-09-11 14:00:05
# Size of source mod 2**32: 682 bytes
import hashlib, re
hashes = [

def main():
    guesses = []
    for i in range(len(hashes)):
        guess = input('Guess: ')
        if len(guess) <= 4 or len(guess) >= 6 or re.match('^[a-z]+$', guess):
        if not re.match('^' + hashes[i].replace('.', '[0-9a-f]') + '$', hashlib.md5(guess.encode()).hexdigest()):
        print(f"Flag: {guesses[0]}" + '{' + ''.join(guesses[1:]) + '}')

if __name__ == '__main__':
# okay decompiling guesser.pyc

At first glance, this seems to be a fairly simple python script, but let's break it down line by line. First we have the declaration of a list of hashes

hashes = [

These will be important in a moment, but for now let's follow the logic to see what the guesser is checking for.

We can see in the main function, we're iterating over the list of hashes, and for each hash, we take a string as user input and check if it's length is equal to 5 AND if it matches the regex string ^[a-z]+$ which would be interpreted as a string of exclusively lowercase alphabetic letters with a length greater than or equal to one. If this condition is met, the program exits and outputs 'Invalid' just as we saw in initial test.

guess = input('Guess: ')
if len(guess) <= 4 or len(guess) >= 6 or re.match('^[a-z]+$', guess):

The second if statement is taking an md5 hash of our guess string and checking that it matches the hash from our hashes list. The hash converts each . (dot) character to [0-9a-f]. This is necessary to only match on valid md5 hashes, otherwise we exit just as before.

if not re.match('^' + hashes[i].replace('.', '[0-9a-f]') + '$', hashlib.md5(guess.encode()).hexdigest()):

And finally, if our guess passes both of those checks it is appended to the guesses list.


This guesses list is joined and printed as the flag output provided the program doesn't exit prematurely by receiving an incorrect guess.

    print(f"Flag: {guesses[0]}" + '{' + ''.join(guesses[1:]) + '}')

One important part of the last line, is that the first element of guesses is used as the beginning of our flag which, according to the flag format should correspond to cvctf. With that in mind we should be able to confirm our understanding of the program by finding the md5 hash of cvctf which should match the first hash in hashes.

We can get the md5 hash by running echo -n cvctf | md5sum in our terminal. This gives us an md5 hash of d70146aef5a8e5364791d3006ccd9c00

Placing the hashes side by side we can see that they match.


We should be able to test this by entering cvctf as our first guess when running the challenge binary.

$ python guesser.pyc
Guess: cvctf
Guess: again

We can see that the program only exited after the guess of "again", meaning the guess of "cvctf" was correct. That's great but you may have noticed this seems to contradict a bit of our analysis. Recall that the first if check appeared to exclude any guesses that were 5 characters in length or all lowercase and alphabetic. This exactly matches our guess of "cvctf"!

Bad Decompilation?

As we can see, the behavior of the program when running the decompiled code does not match the behavior of the original guesser.pyc. Now I tried several decompilers, and as far as I can tell this is an error in the decompilation process. That line in particular should actually have decompiled to this:

if not(len(guess) <= 4 or len(guess) >= 6 or re.match('^[a-z]+$', guess)):

Instead of this

if len(guess) <= 4 or len(guess) >= 6 or re.match('^[a-z]+$', guess):

In this case, the program would exit if the guess is NOT 5 alphabetic characters. This matches the behavior we've seen when running compiled binary and leads us to different assumptions about the possible problem space. Restricting our guess to all lowercase alphabetic characters means we only have $ 26^5 $ possibilities. That comes out to a measly 11,881,376 possible guesses. We should be able to write a program to do that for us. Enter


import hashlib
import re
from pwnlib.util.iters import bruteforce, mbruteforce

hash_patterns = [
hash_regexes = [re.compile(x) for x in hash_patterns]

guess_len = 5
charset = "abcdefghijklmnopqrstuvwxyz"

for regex in hash_regexes:
    print(f"Searching for match for {regex}...")
    found = mbruteforce(lambda guess:
    if found is None:
        print("No matches found")
        print(f"FOUND: {found}, MD5: {hashlib.md5(found.encode()).hexdigest()}")

The program uses pwntools to generate all the possible combinations given our set of lowercase alphabetic characters. It then generates the md5 hash using the hashlib library and compares it against the hash from the hashes list.

$ python
Searching for match for re.compile('^d.0.....f5...$')...
FOUND: cvctf, MD5: d70146aef5a8e5364791d3006ccd9c00
Searching for match for re.compile('^1b.8.1.c........09.30.....64aa9.$')...
FOUND: hashi, MD5: 1bd8d1fc2b9ad2bb0943056ecf64aa97
Searching for match for re.compile('^c.d.1.53..66.4.43bd.......59...8$')...
FOUND: snotg, MD5: cdd01c536d66a4943bd8bf6f5d59c0c8
Searching for match for re.compile('^.d.d.076........eae.3.6.85.a2...$')...
FOUND: uessy, MD5: 8d1d70762f431cd9eaec3967859a2b4b

Et voilĂ , we have our flag! cvctf{hashisnotguessy}