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key.txt

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3.14

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# Практическая работа №5 — Конфиденциальный обмен сообщениями
Клиент-серверное приложение для обмена сообщениями по TCP с поддержкой
шифрования 3DES-CBC (с затравкой), контроля целостности SHA-256 и
аутентификации отправителя HMAC-SHA256.
## Установка
```bash
uv sync
```
## Ключ шифрования
Ключ хранится в текстовом файле (не менее 32 символов). Права на файл — только
чтение владельцем (`600`). Программа проверяет права при запуске и отказывается
работать, если файл доступен группе или другим пользователям.
```bash
openssl rand -hex 32 > key.txt
chmod 600 key.txt
```
## Запуск
### Сервер
```bash
uv run main.py server --port 9000 # без шифрования
uv run main.py server --port 9000 --encrypt # 3DES-CBC
uv run main.py server --port 9000 --encrypt --integrity # + SHA-256
uv run main.py server --port 9000 --encrypt --integrity --test-integrity # отправка с повреждённым хэшем
uv run main.py server --port 9000 --encrypt --hmac # 3DES + HMAC-SHA256
uv run main.py server --port 9000 --hmac # только HMAC (без шифрования)
uv run main.py server --port 9000 --key /path/to/key.txt --encrypt # другой файл ключа
```
### Клиент
```bash
uv run main.py client 127.0.0.1 9000
uv run main.py client 127.0.0.1 9000 --encrypt
uv run main.py client 127.0.0.1 9000 --encrypt --integrity
uv run main.py client 127.0.0.1 9000 --encrypt --integrity --test-integrity
uv run main.py client 127.0.0.1 9000 --encrypt --hmac
uv run main.py client 127.0.0.1 9000 --encrypt --hmac --test-integrity
```
## Режимы работы
| Флаг | Описание |
|------|----------|
| *(без флагов)* | Открытый текст, без проверки целостности |
| `--encrypt` | Шифрование 3DES-CBC с затравкой (соль + IV генерируются случайно для каждого сообщения) |
| `--integrity` | Контроль целостности — к сообщению прикладывается SHA-256 хэш открытого текста |
| `--hmac` | HMAC-SHA256 — контроль целостности + аутентификация отправителя (требует ключ, несовместим с `--integrity`) |
| `--test-integrity` | Режим тестирования: отправляется заведомо некорректный хэш/HMAC (требует `--integrity` или `--hmac`) |
## Анализ трафика с помощью tcpdump
Для наблюдения за передаваемыми данными удобно использовать `tcpdump`.
При работе на одной машине (loopback):
```bash
sudo tcpdump -i lo -X -n tcp port 9000
```
При работе по сети (замените `eth0` на имя сетевого интерфейса):
```bash
sudo tcpdump -i eth0 -X -n tcp port 9000
```
- **Без шифрования** — в дампе видны сообщения открытым текстом (JSON с полем `"data": "текст сообщения"`).
- **С шифрованием** — в дампе видны только шифротекст, соль и IV в hex; читаемый текст отсутствует.

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# Практическая работа №5
по дисциплине «Защита информации»
**Тема работы:** «Разработка клиент-серверного приложения для конфиденциального обмена сообщениями»
**Преподаватель:** Силиненко А.В.
**Email:** a_silinenko@mail.ru
## 1. Цель и задачи работы
### 1.1. Цель работы
Разработка клиент-серверного приложения для конфиденциального обмена сообщениями с использованием шифрования и контроля целостности.
### 1.2. Задачи работы
- получение базовых знаний по использованию криптографических функций библиотеки `crypto` в ОС Linux или другой библиотеки, обеспечивающей реализацию требований задания;
- разработка клиент-серверного приложения для обмена шифрованными сообщениями с контролем целостности;
- проверка работы приложения в различных режимах использования с помощью программы анализа трафика.
## 2. Требования к приложению
### 2.1. Общие требования
Разработать приложение типа «клиент-сервер», позволяющее обмениваться короткими сообщениями между клиентской и серверной частями приложения с обеспечением шифрования и контроля целостности.
### 2.2. Общие требования
- протокол взаимодействия: TCP;
- длина сообщения: не более 80 символов;
- полнодуплексный обмен сообщениями: возможность одновременного приема и передачи сообщений;
- IP-адрес и порт серверной части передается клиентской части приложения в качестве параметров запуска в командной строке;
- приложение должно быть способно функционировать как при запуске клиентской и серверной частей приложения на одном компьютере, так и на разных сетевых узлах;
- язык написания программы: любой.
### 2.3. Требования к функции шифрования
- приложение должно поддерживать функцию шифрования сообщений на основе симметричного шифрования с использованием библиотеки `crypto`, входящей в API `openssl`, или другой аналогичной библиотеки;
- алгоритм симметричного шифрования: согласно индивидуальному заданию;
В моём варианте это 3DES
- ключ шифрования длиной не менее 32 символов задается в файле;
- права доступа к файлу: чтение только владельцем;
- использование опции шифрования задается ключом командной строки при запуске программы.
### 2.4. Требования к функции контроля целостности
- приложение должно поддерживать функцию контроля целостности на основе подсчета хэш-значения передаваемого сообщения;
- алгоритм вычисления хэш-значения - в соответствии с индивидуальным заданием (см. практическую работу №2);
- использование опции контроля целостности задается ключом командной строки при запуске программы;
- предусмотреть режим тестирования, в котором при включенной опции контроля целостности отправляются сообщения с некорректным хэш-значением.
### 2.5. Необязательные требования
- реализовать шифрование с «затравкой» («солью»), обеспечивающей разные шифрованные сообщения при одном и том же открытом тексте;
- реализовать для разработанного приложения опцию выработки и использования сессионного ключа на основе алгоритма Диффи-Хеллмана вместо заранее заданного ключа.
## 3. Требования к отчету
### 3.1. В разделе отчета, посвященном данной работе, должны быть приведены
- актуальность темы работы в контексте курса;
- цели и задачи работы;
- краткое описание особенностей используемого алгоритма симметричного шифрования, а также шифрования «с затравкой» и алгоритма Диффи-Хеллмана, если реализованы соответствующие требования;
- команды компиляции и сборки исполняемых модулей приложения;
- описание процедуры проверки работы приложения с примерами, включая выводы программы анализа трафика, подтверждающие реализацию требований передачи сообщений без шифрования, с шифрованием, с шифрованием и контролем целостности;
- описание проверки опции контроля целостности, в которой отправляются сообщения с некорректным хэш-значением;
- описание проверки шифрования «с затравкой» и алгоритма Диффи-Хеллмана, если реализованы соответствующие требования;
- текст разработанного приложения (клиентской и серверной частей) с комментариями - в приложении к отчету;
- выводы по проделанной работе.

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from __future__ import annotations
import argparse
import hashlib
import hmac
import json
import os
import socket
import stat
import struct
import sys
import threading
from cryptography.hazmat.decrepit.ciphers.algorithms import TripleDES
from cryptography.hazmat.primitives.ciphers import Cipher, modes
from cryptography.hazmat.primitives import padding as sym_padding
MAX_MSG_LEN = 80
DEFAULT_KEY_FILE = "key.txt"
def check_key_permissions(path: str) -> None:
st = os.stat(path)
mode = st.st_mode
bad = stat.S_IRGRP | stat.S_IWGRP | stat.S_IXGRP | stat.S_IROTH | stat.S_IWOTH | stat.S_IXOTH
if mode & bad:
current = oct(mode & 0o777)
print(f"[!] Key file permissions too open ({current}): {path}")
print(f" Run: chmod 600 {path}")
sys.exit(1)
def load_key(path: str) -> str:
if not os.path.isfile(path):
print(f"[!] Key file not found: {path}")
sys.exit(1)
check_key_permissions(path)
with open(path) as f:
key = f.read().strip()
if len(key) < 32:
print(f"[!] Key must be at least 32 characters (got {len(key)})")
sys.exit(1)
return key
def derive_3des_key(file_key: str, salt: bytes) -> bytes:
return hashlib.sha256(file_key.encode() + salt).digest()[:24]
def encrypt_message(plaintext: str, file_key: str) -> tuple[bytes, bytes, bytes]:
salt = os.urandom(16)
key = derive_3des_key(file_key, salt)
iv = os.urandom(8)
padder = sym_padding.PKCS7(64).padder()
padded = padder.update(plaintext.encode()) + padder.finalize()
encryptor = Cipher(TripleDES(key), modes.CBC(iv)).encryptor()
ct = encryptor.update(padded) + encryptor.finalize()
return salt, iv, ct
def decrypt_message(salt: bytes, iv: bytes, ct: bytes, file_key: str) -> str:
key = derive_3des_key(file_key, salt)
decryptor = Cipher(TripleDES(key), modes.CBC(iv)).decryptor()
padded = decryptor.update(ct) + decryptor.finalize()
unpadder = sym_padding.PKCS7(64).unpadder()
plaintext = unpadder.update(padded) + unpadder.finalize()
return plaintext.decode()
def compute_hash(text: str) -> str:
return hashlib.sha256(text.encode()).hexdigest()
def compute_hmac(file_key: str, text: str, salt: bytes) -> str:
return hmac.new(file_key.encode(), text.encode() + salt, hashlib.sha256).hexdigest()
def recv_exactly(sock: socket.socket, n: int) -> bytes | None:
buf = b""
while len(buf) < n:
chunk = sock.recv(n - len(buf))
if not chunk:
return None
buf += chunk
return buf
def send_packet(sock: socket.socket, data: bytes) -> None:
sock.sendall(struct.pack("!I", len(data)) + data)
def recv_packet(sock: socket.socket) -> dict | None:
header = recv_exactly(sock, 4)
if header is None:
return None
length = struct.unpack("!I", header)[0]
payload = recv_exactly(sock, length)
if payload is None:
return None
return json.loads(payload.decode())
def do_send(
sock: socket.socket,
text: str,
file_key: str | None,
use_encrypt: bool,
use_integrity: bool,
use_hmac: bool,
test_integrity: bool,
) -> None:
msg: dict = {}
print(f" [TX] plaintext: {text}")
enc_salt: bytes | None = None
if use_encrypt:
assert file_key is not None
salt, iv, ct = encrypt_message(text, file_key)
enc_salt = salt
derived_hex = derive_3des_key(file_key, salt).hex()
msg["encrypted"] = True
msg["salt"] = salt.hex()
msg["iv"] = iv.hex()
msg["data"] = ct.hex()
print(f" [TX] salt: {salt.hex()}")
print(f" [TX] 3DES key: {derived_hex}")
print(f" [TX] IV: {iv.hex()}")
print(f" [TX] ciphertext: {ct.hex()}")
else:
msg["encrypted"] = False
msg["data"] = text
if use_integrity:
h = compute_hash(text)
if test_integrity:
h = hashlib.sha256(b"CORRUPTED_" + os.urandom(4)).hexdigest()
print(f" [TX] SHA-256: {h} (CORRUPTED!)")
else:
print(f" [TX] SHA-256: {h}")
msg["hash"] = h
if use_hmac:
assert file_key is not None
hmac_salt = enc_salt if enc_salt is not None else os.urandom(16)
h = compute_hmac(file_key, text, hmac_salt)
msg["hmac_salt"] = hmac_salt.hex()
if test_integrity:
h = hmac.new(b"WRONG_KEY", os.urandom(8), hashlib.sha256).hexdigest()
print(f" [TX] HMAC salt: {hmac_salt.hex()}")
print(f" [TX] HMAC-256: {h} (CORRUPTED!)")
else:
print(f" [TX] HMAC salt: {hmac_salt.hex()}")
print(f" [TX] HMAC-256: {h}")
msg["hmac"] = h
send_packet(sock, json.dumps(msg).encode())
print()
def do_recv(
msg: dict,
file_key: str | None,
) -> str | None:
encrypted = msg.get("encrypted", False)
if encrypted:
salt = bytes.fromhex(msg["salt"])
iv = bytes.fromhex(msg["iv"])
ct = bytes.fromhex(msg["data"])
print(f" [RX] ciphertext: {ct.hex()}")
print(f" [RX] salt: {salt.hex()}")
print(f" [RX] IV: {iv.hex()}")
if file_key is None:
print(" [RX] ERROR: message is encrypted but no key loaded")
return None
derived_hex = derive_3des_key(file_key, salt).hex()
print(f" [RX] 3DES key: {derived_hex}")
try:
text = decrypt_message(salt, iv, ct, file_key)
except Exception as e:
print(f" [RX] decryption failed: {e}")
return None
print(f" [RX] decrypted: {text}")
else:
text = msg["data"]
print(f" [RX] plaintext: {text}")
if "hash" in msg:
received_hash = msg["hash"]
computed_hash = compute_hash(text)
ok = received_hash == computed_hash
print(f" [RX] recv hash: {received_hash}")
print(f" [RX] calc hash: {computed_hash}")
if ok:
print(" [RX] integrity: OK")
else:
print(" [RX] integrity: FAIL - message may have been tampered with!")
if "hmac" in msg:
hmac_salt = bytes.fromhex(msg["hmac_salt"])
received_hmac = msg["hmac"]
if file_key is None:
print(" [RX] ERROR: HMAC present but no key loaded")
else:
computed_h = compute_hmac(file_key, text, hmac_salt)
ok = hmac.compare_digest(received_hmac, computed_h)
print(f" [RX] HMAC salt: {hmac_salt.hex()}")
print(f" [RX] recv HMAC: {received_hmac}")
print(f" [RX] calc HMAC: {computed_h}")
if ok:
print(" [RX] HMAC auth: OK - sender verified")
else:
print(" [RX] HMAC auth: FAIL - sender NOT verified!")
print()
return text
def receiver_thread(
sock: socket.socket,
file_key: str | None,
stop_event: threading.Event,
) -> None:
try:
while not stop_event.is_set():
msg = recv_packet(sock)
if msg is None:
print("\n[*] Connection closed by remote side.")
stop_event.set()
break
do_recv(msg, file_key)
except OSError:
if not stop_event.is_set():
print("\n[*] Connection lost.")
stop_event.set()
def sender_thread(
sock: socket.socket,
file_key: str | None,
use_encrypt: bool,
use_integrity: bool,
use_hmac: bool,
test_integrity: bool,
stop_event: threading.Event,
) -> None:
try:
while not stop_event.is_set():
try:
text = input()
except EOFError:
stop_event.set()
break
if stop_event.is_set():
break
if len(text) > MAX_MSG_LEN:
print(f" [!] Message too long ({len(text)} > {MAX_MSG_LEN}), truncated.")
text = text[:MAX_MSG_LEN]
do_send(sock, text, file_key, use_encrypt, use_integrity, use_hmac, test_integrity)
except OSError:
if not stop_event.is_set():
stop_event.set()
def run_session(
sock: socket.socket,
addr: tuple,
file_key: str | None,
use_encrypt: bool,
use_integrity: bool,
use_hmac: bool,
test_integrity: bool,
) -> None:
flags = []
if use_encrypt:
flags.append("3DES")
if use_integrity:
flags.append("SHA-256")
if use_hmac:
flags.append("HMAC-SHA256")
if test_integrity:
flags.append("test-integrity")
mode_str = ", ".join(flags) if flags else "plaintext"
print(f"[*] Session with {addr[0]}:{addr[1]} [{mode_str}]")
print("[*] Type messages and press Enter to send. Ctrl+C / Ctrl+D to quit.\n")
stop = threading.Event()
rx = threading.Thread(target=receiver_thread, args=(sock, file_key, stop), daemon=True)
tx = threading.Thread(target=sender_thread, args=(sock, file_key, use_encrypt, use_integrity, use_hmac, test_integrity, stop), daemon=True)
rx.start()
tx.start()
try:
while not stop.is_set():
stop.wait(0.5)
except KeyboardInterrupt:
print("\n[*] Interrupted.")
stop.set()
sock.close()
def run_server(args: argparse.Namespace) -> None:
file_key = load_key(args.key) if (args.encrypt or args.hmac) else None
srv = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
srv.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
srv.bind(("0.0.0.0", args.port))
srv.listen(1)
print(f"[*] Listening on 0.0.0.0:{args.port} ...")
conn, addr = srv.accept()
print(f"[*] Client connected: {addr[0]}:{addr[1]}")
srv.close()
run_session(conn, addr, file_key, args.encrypt, args.integrity, args.hmac, args.test_integrity)
def run_client(args: argparse.Namespace) -> None:
file_key = load_key(args.key) if (args.encrypt or args.hmac) else None
sock = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
sock.connect((args.host, args.port))
print(f"[*] Connected to {args.host}:{args.port}")
run_session(sock, (args.host, args.port), file_key, args.encrypt, args.integrity, args.hmac, args.test_integrity)
def build_parser() -> argparse.ArgumentParser:
parser = argparse.ArgumentParser(description="Encrypted messaging (3DES-CBC + SHA-256)")
sub = parser.add_subparsers(dest="role", required=True)
for name, sp in [("server", sub.add_parser("server", help="Start server")),
("client", sub.add_parser("client", help="Start client"))]:
if name == "server":
sp.add_argument("--port", type=int, required=True)
else:
sp.add_argument("host")
sp.add_argument("port", type=int)
sp.add_argument("--encrypt", action="store_true", help="Enable 3DES-CBC encryption")
sp.add_argument("--integrity", action="store_true", help="SHA-256 integrity check")
sp.add_argument("--hmac", action="store_true", help="HMAC-SHA256 integrity + authentication")
sp.add_argument("--test-integrity", action="store_true", help="Send corrupted hash/HMAC")
sp.add_argument("--key", default=DEFAULT_KEY_FILE, help="Path to key file (default: key.txt)")
return parser
def main() -> None:
args = build_parser().parse_args()
if args.integrity and args.hmac:
print("[!] --integrity and --hmac are mutually exclusive")
sys.exit(1)
if args.test_integrity and not (args.integrity or args.hmac):
print("[!] --test-integrity requires --integrity or --hmac")
sys.exit(1)
if args.role == "server":
run_server(args)
else:
run_client(args)
if __name__ == "__main__":
main()

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[project]
name = "lab5"
version = "0.1.0"
description = "Add your description here"
readme = "README.md"
requires-python = ">=3.14"
dependencies = [
"cryptography>=46.0.6",
]

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version = 1
revision = 3
requires-python = ">=3.14"
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version = "2.0.0"
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dependencies = [
{ name = "pycparser", marker = "implementation_name != 'PyPy'" },
]
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