The challenge consists of two services communicating with each other: on port 1337 and on port 1338.


Most part of the provided services is used for initializing AES, which is done with a protocol very similar to TLS. In the following I will explain the initialization in the order of the communication and will therefore switch between and

c l i e n t R S A s i e g n A n c E e r S c d s y l e p e A i h A r t n E e a E v e A c S n s S e d E r t h r S y m m p p o r o o r r m t d a f d a e o e e n e n m d d s d c s d a e o e o s f m r m t i t e n i r i f s i s h c e a c t r e e t s e r v e r

Both scripts start with the same imports and by defining the supported AES modes:

from Crypto.Util.Padding import pad, unpad
from Crypto.PublicKey import RSA
from Crypto.Cipher import AES, PKCS1_OAEP
from Crypto.Hash import SHA256
from Crypto.Signature import PKCS1_v1_5

import random
import string

from fields import cert, block_size
from secret import flag


The initialization begins at the client by generating four random characters and sending them together with the supported AES modes to the server. TLS uses much larger random values (32 byte) and will send some additional information such as the protocol version.

########## Client Hello ##########
# Cipher suite
print(*cipher_suite.keys(), sep=', ')

client_random = ''.join(random.SystemRandom().choice(string.ascii_uppercase + string.digits) for _ in range(4))
# Client random

The server receives both and stores them for later use.

########## Client Hello ##########
# Enter encryption methods
input_encryptions_suite = input()
client_cipher_suite = input_encryptions_suite.split(", ")
# Enter client random
client_random = input()

Now the server proceeds with sending his own hello, starting with a signed hash of his certificate. In TLS, the server would send the actual certificate and a signed hash of all previous messages.

########## Server Hello ##########

# Certificate
private_key = RSA.import_key(open("my_credit_card_number.pem").read())
cipher_hash =
signature =
#Signed certificate

After that the server computes the intersection of the AES modes supported by him and the client and sends the resulting list back to the client. In TLS, the server chooses one of the ciphers that is understood by client and server and sends only the selected cipher to the client.

# select cipher suite
selected_cipher_suite = {}
for method in cipher_suite:
    if method in client_cipher_suite:
        selected_cipher_suite[method] = cipher_suite[method]

if len(selected_cipher_suite) == 0:
    print("Honey, we have a problem. I'm sorry but I'm disowning you :(")

# Selected cipher suite
print(*selected_cipher_suite.keys(), sep=', ')

Finally, the server generates four random characters and sends them to the client. As with the client random, TLS will generate a 32 byte long random value.

server_random = ''.join(random.SystemRandom().choice(string.ascii_uppercase + string.digits) for _ in range(4))
# Server random

Now back to the client. It first loads the preshared public key of the server and verifies the signature. As the certificate is preshared in this case, the server didn’t have to send it. Furthermore in TLS the public key would be read from the certificate and not from a separate file. As an alternative to certificates, TLS supports the Diffie-Hellman key exchange, which is covered in last years UIUCTF challenge dhke_intro.

########## Server Hello ##########

# verify server
# Enter signed certificate
server_signature_hex = input()
server_signature = bytearray.fromhex(server_signature_hex)
public_key = RSA.import_key(open("receiver.pem").read())
cipher_hash =
verifier =

if not verifier.verify(cipher_hash, server_signature):
    print("Mom told me not to talk to strangers.")

As next step, the client parses the cipher suits supported by the server.

# Enter selected cipher suite
input_encryptions_suite = input()
if len(input_encryptions_suite) == 0:
    print(" nO SeCUriTY :/")

selected_cipher_suite = {}
input_encryptions_suite = input_encryptions_suite.split(", ")
for method in input_encryptions_suite:
    if method in cipher_suite:
        selected_cipher_suite[method] = cipher_suite[method]

if len(selected_cipher_suite) == 0:
    print("I'm a rebellious kid who refuses to talk to people who don't speak my language.")

As last part of the parsing of the server hello, the random characters from the server are stored for later use.

# Enter server random
server_random = input()

As next step, the client initializes AES, starting with the generation of the premaster secret. This is then encrypted and send to the server. As in previous cases, the premaster secret of TLS is larger and uses 48 bytes.

premaster_secret = ''.join(random.SystemRandom().choice(string.ascii_uppercase + string.digits) for _ in range(8))

cipher_rsa =
premaster_secret_encrypted = cipher_rsa.encrypt(premaster_secret.encode()).hex()
# Encrypted premaster secret

Then the session key is computed from the previously generated premaster secret and both random values. Because the premaster secret is send encrypted, the session key is only known to the client and server. The use of client and server random prevents replay attacks, as the target of the replay will choose a different one. This is especially true for TLS, since 4 of the 32 bytes of the client and server random are the current timestamp.

session_key = + server_random + premaster_secret).encode()).hexdigest()

Now the client chooses one of the ciphers supported by client and server and informs the server about the selected cipher.

chosen_cipher_name = next(iter(selected_cipher_suite))
# Using encryption mode
cipher =[:16], cipher_suite[chosen_cipher_name])

The server receives the premaster secret, decrypts it with its private key and uses it to calculate the same session key.

########## ClientKeyExchange & CipherSpec Finished ##########
# Enter premaster secret
encrypted_premaster_secret = input()
cipher_rsa =
premaster_secret = cipher_rsa.decrypt(bytearray.fromhex(encrypted_premaster_secret)).decode('utf-8')

session_key = + server_random + premaster_secret).encode()).hexdigest()

After that, the server will check wether the selected cipher is one of the supported ones and will then initialize AES with the session key and the selected mode.

# Enter chosen cipher
chosen_cipher_name = input()
if chosen_cipher_name not in selected_cipher_suite:
    print("No honey, I told you we're not getting ", chosen_cipher_name, '.', sep='')
cipher =[:16], cipher_suite[chosen_cipher_name])

Finally the client sends an AES encrypted finish to the server.

# Encrypted finish message
print(cipher.encrypt(pad(b"finish", block_size)).hex())

The server decrypts the finish and checks wether it is correct. This is a final proof, that both sides have calculated the same session key.

# Enter encrypted finish
client_finish = input()
client_finish = bytearray.fromhex(client_finish)

########## ServerKeyExchange & CipherSpec Finished ##########

finish_msg = unpad(cipher.decrypt(client_finish), block_size)
assert(finish_msg == b'finish')

In TLS, the server would also send a finish message over the encrypted channel to proof the client the it has the same session key. In this challenge, the message is not send but the client wants to receive an unencrypted finish and checks it.

########## ServerKeyExchange & CipherSpec Finished ##########
# Confirm finish
finish_msg = input()
assert(finish_msg == "finish")

Now the connection is established and the contents can be exchanged.

The server checks each message if it exactly matches the flag and prints a message indicating the result.

########## Communication ##########

# Listening...
while True:
    client_msg = input()
    client_msg = unpad(cipher.decrypt(bytearray.fromhex(client_msg)), block_size)

    if client_msg == flag:
        print("That is correct.")
        print("You are not my son.")

This has little to no interest for us, since we would have to guess the whole flag at once, which is way to much effort. We can only use it to verify the flag.

The client is much more useful. It requests a hex-encoded prefix, appends the flag to the decoded prefix and prints the AES encrypted result.

########## Communication ##########

while True:
    prefix = input()
    if len(prefix) != 0:
        prefix = bytearray.fromhex(prefix)
        extended_flag = prefix + flag
        extended_flag = flag
    ciphertext = cipher.encrypt(pad(extended_flag, block_size)).hex()

This enables us to brute force the flag character by character, which can be done in a few minutes.


For solving the challenge, we used pwntools’ remote for the communication with the services and python’s string to obtain a list of flag characters.

from pwn import *
import string

First we have to initialize the connection to the client. Therefore we connect to the client and server and relay the messages from the server to the client and vice versa.

After connecting to the services,

def get_services():
    # connect to server and client
    server = remote("", 1337)
    client = remote("", 1338)

the services will send == proof-of-work: disabled ==\n, which we have to skip, since this is not part of the protocol.

    # skip proof of work message

As first message, the client will send us the supported AES modes. As we want to use ECB, we drop the received list and send only AES.MODE_ECB to the server. We will explain this decision later, when we actually use the properties of this mode.

    # AES modes

The remaining initialization can be relayed.

    # client random

    # server signature

    # server AES mode

    # server random

    # client encrypted premaster secret

    # client chosen AES mode

    # client finish
    finish = client.recvline()

Since the client expects a plain text finish and the server does not send it, we must send it ourselves. After that we have a server and a client in their main loop, which can be returned.

    # send finish for client

    return server, client

Now we come to the actual exploit and the chosen AES mode.

AES works by dividing the message to encrypt in blocks of 16 bytes. The difference between the modes is the handling of these blocks. The simplest mode is Electronic CodeBook (ECB), which just takes each block and encrypts it separately. This has the effect, that the same plain text block will always result in the same encrypted block. Because of this, structures are retained. A popular example for this property is the ECB encrypted Tux. As a result of this insecureness, ECB is not part of the ciphers available in TLS.

c p i l p a e h i n e n c r t r t e y e x p x t t t 1 1 c p i l p a e h i n e n c r t r t e y e x p x t t t 2 2

We can use this insecureness to our advantage. If we send a prefix, the flag is moved to the right, resulting in a different alignment against the block boundaries. By changing the length of the prefix, we can adjust the position of the flag relative to the block boundaries. In the example below we used underscores as prefix.

      block 1          block 2
|uiuctf{FAKEFLAG}|                |
|_______________u|iuctf{FAKEFLAG} |
|______________ui|uctf{FAKEFLAG}  |

Let’s assume, we already know the first character (which we do, since all flags start with uiuctf{). We now can guess the second character by appending the prefix used in the last row of the above example with the already known part of the flag and our guess. If we guess the correct character, the first block will be identical to the one requested with only the underscores.

     block 1          block 2
|______________ui|uctf{FAKEFLAG}  |
|                |                |

With this knowledge we can begin to write the function for brute forcing one character. It takes a connection to a client, the already guessed flag and the alphabet to use as parameters. At first we request the encrypted blocks to search for by sending only the prefix. This results in the flag being moved to the right, such that the second block will end one character after the already guessed flag characters. Since the encrypted flag spans over two blocks, we send a prefix of 32 minus the number of wanted flag characters as prefix.

For converting the string to hex, we have to convert the string to bytes first and can then convert them to hex. As pwntools needs the data to send as bytes and the returned hex representation is a string, we have to encode it again.

def brute_force_char(client, flag, alphabet):
    # get encrypted flag part

As the remaining blocks won’t match, since they contain the remaining flag characters in the search request and the whole flag in the guess requests, we keep only the hex representation of the first two blocks, i.e. 64 hex characters.

    search = client.recvline()[:64]

Now we can iterate over the given alphabet and test each character.

    # precompute prefix
    prefix = "A"*(31-len(flag)) + flag

    # iterate over alphabet
    for c in alphabet:
        # encrypt guess
        client.sendline((prefix + c).encode().hex().encode())
        recv = client.recvline()[:64]

If the received blocks match with the search pattern, we have found the next flag character and can abort the loop

        # return if correct char found
        if recv == search:
            return c

As we now have the initialization of the services and the brute forcing of one flag character done, we can develope the main control flow and define the alphabet of the flag. string.printable contains all printable ASCII characters, including whitespace.

ALPHABET = string.printable

Furthermore we can define the known start of the flag, as its the same format for all challenges

flag = "uiuctf{"

Before starting the brute forcing, we have to get a client. Since we do not need the server, we can close it.

# get services
server, client = get_services()

# close server

Now we brute force the flag character by character until we reach the closing curly brace.

while flag[-1] != "}":
    flag += brute_force_char(client, flag, ALPHABET)

    # print progress

By running this script, we get the flag after less than two minutes: uiuctf{AES_@_h0m3_b3_l1ke3}.


The acquisition of the search blocks can be optimized by requesting only each of the possible 16 offsets of the flag in a block once and then reusing them. The following example demonstrates this by brute forcing the second (compare only the first block) and the 18. character of the flag (compare the first two blocks).

     block 1          block 2          block 3          block 4
|______________ui|uctf{LONGFAKEFLA|G}              |                |
|                |                |                |                |
|______________u?|uiuctf{LONGFAKEF|LAG}            |                |
|______________ui|uiuctf{LONGFAKEF|LAG}            |                |
|                |                |                |                |
|______________ui|uctf{LONGFAKEFL?|uiuctf{LONGFAKEF|LAG}            |
|______________ui|uctf{LONGFAKEFLA|uiuctf{LONGFAKEF|LAG}            |

This strategy would require to first request all possible search offsets:

searchs = []
for i in range(16):

brute_force_char would then use up to 15 prefix characters and compare as many blocks as needed to include characters up to the guessed one.

def brute_force_char(client, flag, alphabet, searchs):
    # precompute prefix
    prefix = "A"*(15 - len(flag)%16) + flag

    # calculate length of hex representation of prefix + guess
    compare_length = 2 * (len(prefix)+1)

    # get search blocks
    search = searchs[len(flag)%16][:compare_length]

    # iterate over alphabet
    for c in alphabet:
        # encrypt guess
        client.sendline((prefix + c).encode().hex().encode())
        recv = client.recvline()[:compare_length]

        # return if correct char found
        if recv == search:
            return c

The main loop remains identical, except from searchs being passed as third parameter to brute_force_char. Since the flag only contains 27 characters, this optimization saves 11 requests, which is negligible compared to the up to 93 tries for the closing curly brace.


The approach used in the exploit can be parallelized by using multiple connections. Since the session key will be different for each connection, the encrypted plain text and therefore the search pattern will be different and must be requested for each session. Then the alphabet can be distributed between the connections.

A good library for this is python’s concurrent.futures library. It allows to distribute tasks between a defined number of workers and returning finished tasks without manually querying all workers. Furthermore we will use the threading library to store data at the worker threads and ceil from the math library.

import concurrent.futures as cf
import threading
import math

The main part of concurrent.futures are the executors. They control the workers and distribute the tasks. concurrent.futures offers two types of executors: ThreadPoolExecutor and ProcessPoolExecutor. As the names indicate, the former one uses threads and the later one subprocesses for it’s workers. Concurrency can be solved in multiple ways. Python decided to use the easiest and safest one by introducing the global interpreter lock. This lock ensures, that there is always only one thread executing bytecode. In contrast to threads, subprocesses are, as the name indicates, separate processes, resulting in having an own global interpreter lock for each process. As a consequence, the access to variables outside the process is limited. Furthermore ProcessPolExecutor cannot be used inside the python console. Since the requests are I/O bound tasks with negligible computing time, there should be no noticeable difference between those two executors. But as threads are more light weight, they can be spawned a bit faster. Because of the beforementioned advantages of threads, we will take the ThreadPoolExecutor.

Since we want to reuse clients for multiple requests, we have to initialize the workers first. Since each client has a different session key, we have to request the search pattern for each client and therefore store it together with the corresponding flag part in the client.

def init_worker():
    # get services
    server, client = get_services()

    # close server

    # set additional client attributes
    client.flag = None = None

    # store client with the thread
    threading.current_thread().client = client

Now we can adjust the brute force function, which will be executed by the threads. Each run will try only one character. We first have to ensure, that the blocks to search for are the ones for the current flag character. Then we can request the encryption of our try and return the result of the comparison together with the tested character.

def try_character(flag, char):
    # get client
    client = threading.current_thread().client

    # test if search pattern is for current flag character
    if client.flag != flag:
        # get encrypted flag part
        client.sendline(("A"*(31-len(flag))).encode().hex().encode()) = client.recvline()[:64]

    # test character
    client.sendline(("A"*(31-len(flag)) + flag + char).encode().hex().encode())
    test = client.recvline()[:64]

    # return test result
    return test ==, char

After we having all prerequisites, we can now rebuild the main control flow, starting with the already known definitions of the flag start and the alphabet.

flag = "uiuctf{"
ALPHABET = string.printable

Now we can create the executor. We choose each thread to handle up to five characters, which results in every sixth request being one for the search pattern.

max_workers = math.ceil(len(ALPHABET)/5)
executor = cf.ThreadPoolExecutor(max_workers=max_workers, initializer=init_worker)

The main loop looks different this time, since we have to deal with the executor and its results. Since we want to pass the already brute forced part of the flag to try_character, we cannot use the map function of the executor and must submit each call ourselves.

while flag[-1] != "}":
    # get futures
    futures = [executor.submit(try_character, flag, c) for c in ALPHABET]

After having a list with futures, we have to resolve them. By using as_completed, we get completed futures independent of the order in the passed list. As before, we stop the loop when we found the next flag character.

    # handle results
    for future in cf.as_completed(futures):
        result, char = future.result()
        if result:
            flag += char

But stopping the loop won’t stop the executor from executing the futures, so we have to cancel them ourselves. The cancellation of the remaining futures will reduce the runtime from around 30 seconds to around 22 seconds.

    # cancel remaining futures
    for future in futures:

Other Modes

In our exploit we used the ECB mode, as it is the easiest one, but other modes can also be used after slight adjustments. So let’s have a closer look on the other AES modes featured in this challenge.


The CounTeR mode encrypts the concatenation of a 64 bit nonce and a 64 bit counter and xors the result with the plaintext. Since the nonce and the session key will be different for each connection, the encrypted nonce+counter cannot be predicted. It is possible to infer the encrypted nonce+counter by sending a prefix large enough to know the plaintext of an entire block. But since we do not know the session key, this doesn’t enables us to predict the next one. Since encrypting something with AES will result in an equal chance of a bit being 0 or 1, we do not know the encrypted nonce+counter or we have no unknown bit in the plaintext and are therefore unable to infer the flag with this mode. Counter mode has the advantage, that its keys can be precomputed and then xored over the plaintext. Furthermore this mode only requires the possibility to encrypt and is therefore easier to implement.

p l a i n t e x t 1 n o n c c i e p e h n e c x r 0 r o t 0 y r e 0 p x 0 t t 0 0 1 0 1 p l a i n t e x t 2 n o n c c i e p e h n e c x r 0 r o t 0 y r e 0 p x 0 t t 0 0 2 0 2


The Output FeedBack mode starts with encrypting the initialization vector. It then xors the result with the plaintext. For subsequent blocks, the output of the encryption of the previous block is used instead of the initialization vector. Since the initialization vector is not defined, the used python library will generate it randomly. Using this mode has the same consequences as using the counter mode: we can get the output of the encryption by providing 16 known bytes of plaintext or we can include unknown bits in the plaintext but are unable to infer them, since there is an equal chance of the unknown bits to be flipped or not, as the corresponding bits of the encryption result have an equal probability of being 0 or 1. As a consequence, this mode is unsuitable for solving the challenge. Its has the same advantages as the counter mode but has the disadvantage that it is not possible to decode a block without generating all previous keys.

p l a i n t e x t i n 1 i t i c a i l p i e h z n e a c x r t r o t i y r e o p x n t t v 1 e c t o r p l a i n t e x t 2 c i p e h n e c x r r o t y r e p x t t 2


In EAX mode, AES will output a tuple with two values. The first one is the plaintext encoded with counter mode and the second one is a tag, which can be used for authentication. Since counter mode is used to generate the plaintext and the tag is generated from the ciphertext, a header unrelated to the plain text and the nonce from counter mode, it is also inappropriate for solving this challenge.


The only mode left is Cipher Block Chaining. It starts with an initialization vector, which is not set in our case and therefore randomly generated. It then xors the initialization vector with the plaintext and encrypts the result. For subsequent blocks, the ciphertext of the previous block is used instead of the initialization vector. This has the effect, that the decryption of each block depends only on the session key and the ciphertext of the previous block, which enables the decryption without decryption of random blocks. Since we know the ciphertext of the previous block and are able to set the prefix of the plaintext freely, we can use this mode to solve the challenge. So let’s implement it. Since it might be easier to understand if we implement it without multithreading, we will leave the parallelization and other optimizations to the reader.

i n i t i a l i z a t i o n v e c t o r c p i l p a e h i n e n x c r t o r t e r y e x p x t t t 1 1 c p i l p a e h i n e n x c r t o r t e r y e x p x t t t 2 2

The get_services function from the original exploit must be slightly adjusted. We can either choose AES.MODE_CBC directly or just relay the original list and let the client choose it later, as it is the first mode in the list and therefore the default of this challenge.

    # relay AES mode list -> client will choose AES.MODE_CBC

Since the last ciphertext block is a relevant property in CBC, we will store it with the connection. The first ciphertext we receive is the encrypted finish for the server. We can store it directly before the return of get_services. The client pads the finish message to 32 bytes despite it being shorter than 16 bytes and therefore fitting into only one block. This indicates, that the challenge author set block_size to 32 bytes. Furthermore we have to strip the new line at the end of the response.

    # save last ciphertext block
    client.last = finish.strip()[-32:]

The main control flow can be left unchanged.

Unfortunately python does not natively support xoring variables of type bytes, so we have to write our own helper function. As the right side will always be the raw hex ciphertext, we will also handle the transformation in this helper function.

def bytes_xor_hex(left, hex_right):
    return bytes(l^r for l, r in zip(left, bytes.fromhex(hex_right.decode())))

Now we have to actually exploit the challenge. The basic strategy stays the same: we brute force the flag character by character and by aligning the character to brute force against the end of a block. The only thing to do is the xor. Since we cannot xor the flag appended to the prefix, we will leave the entire search request unchanged.

def brute_force_char(client, flag, alphabet):
    # get encrypted flag part
    response = client.recvline()
    search = response[:64]

For getting comparable ciphertexts, we have to revert the expected xor with the last ciphertext and apply the xor used for search. We have to do it only for the first block, because we only change the plaintext from the last character of the second block onwards. By xoring with the last ciphertext block and the one before the first search block, the ciphertext of the first block will be the same as the first one in search.

    # precompute prefix ^ search
    prefix = ("A"*(31-len(flag)) + flag).encode()
    prefix = bytes_xor_hex(prefix[:16], client.last) + prefix[16:]

Since we no longer need client.last and can update it with the last block of the last ciphertext.

    client.last = response.strip()[-32:]

Now we can try all characters of the alphabet. For each request, we have to revert the upcoming xor by xoring with the last ciphertext.

    for c in alphabet:
        # encrypt guess
        request = bytes_xor_hex(prefix[:16], client.last) + prefix[16:] + c.encode()
        response = client.recvline()

        # Update last ciphertext block
        client.last = response.strip()[-32:]

        # return if correct char found
        if response[:64] == search:
            return c

And now we get the flag in approximately the same time as the first exploit, even without forcing the client to use ECB.