but_why.py

#!/usr/bin/env python3

import string
import random
import os
import shutil
import glob

challengeText = """Here is a carefully prepared file. You must find the flag within!"""

# you can add more fake flags here, or taunts, your call! :) 
fakeFlags = [
    "flag{yeah not the flag you are looking for}",
    "flag{Nope, not the flag}",
    "flag{Totally not the flag}",
    "flag{Never gonna give you the flag}",
    "flag{These aren't the flags you are looking for}",
    "flag{Fake flag! How obnoxious!}",
    "flag{This is bait!}",
]

# the real flag. 
flag = "flag{h0pe_you_aut0mated_this!}"

# How many fake files we want per directory
maxFakeFiles = 5

# How many rounds of nesting do we want? Set this to a reasonable level, this is the example level that can be manually verified. 
maxNestedArchives = 2

def randomString(length):
    return ''.join(random.choice(string.ascii_letters) for i in range(length))

# Used to select a random archive type
def randomArchiveFormatName():
    return random.choice([i[0] for i in shutil.get_archive_formats()])


def dumpToFile(data,path='./'):
    name = randomString(20)
    fn = open(path + name,'w')
    fn.write(data)
    fn.close()
    return name


def makeChallenge():
    # all dirnames and filenames are random. 
    # create a directory
    dirName = randomString(20)
    os.mkdir(dirName)
    # stash the flag inside
    dumpToFile(flag,f'./{dirName}/')
    fileName = randomString(20)
    # ok, now we archive it with a random format. 
    shutil.make_archive(fileName, randomArchiveFormatName(), dirName)
    # remove the original dir, so we only have the archive.
    shutil.rmtree(dirName)
    # We got the flag tucked safely away, now let's rock and roll and wrap this in multiple layers
    for layer in range(maxNestedArchives):
         # create a random dir and move the compressed archive inside.
         dirName = randomString(20)
         os.mkdir(dirName)
         # we want purty fileNames
         shutil.move(glob.glob(fileName+'*')[0], fileName)
         shutil.move(fileName, dirName)
         # add up to maxFakeFiles random flagfiles
         for i in range(random.randint(1,maxFakeFiles)):
             dumpToFile(random.choice(fakeFlags),f'./{dirName}/')
         # archive all that into a new archive file
         fileName = randomString(20)
         shutil.make_archive(fileName, randomArchiveFormatName(), dirName)
         # remove the old tree
         shutil.rmtree(dirName)


if __name__ == '__main__':
    print(challengeText)
    makeChallenge()