Initial commit

.gitignore

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+**/__pycache__/*
+server/app/migrations
+server/database.sqlite
+*.pem

client/api.py

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+import requests
+
+class APIError(Exception):
+    "A custom error we'll use when something goes wrong with the API"
+
+class SubRosaAPI:
+    """An API for the SubRosa server.
+    """
+
+    def __init__(self, url):
+        self.url = url
+
+    def get_user(self, username):
+        route = "/users"
+        params = {'name': username}
+        return self.get(route, params)
+
+    def create_user(self, username, public_key):
+        route = "/users/new"
+        params = {'name': username, 'public_key': public_key}
+        return self.post(route, params)
+
+    def get_messages(self, username):
+        route = "/messages"
+        params = {'name': username}
+        return self.get(route, params)
+
+    def send_message(self, sender, recipient, ciphertext, time_sent, time_sent_signature):
+        route = "/messages/send"
+        params = {
+            'sender': sender, 
+            'recipient': recipient,
+            'ciphertext': ciphertext,
+            'time_sent': time_sent,
+            'time_sent_signature': time_sent_signature,
+        }
+        return self.get(route, params)
+
+    def get(self, route, params):
+        response = requests.get(self.url + route, json=params)
+        if response.ok:
+            return response.json()
+        else:
+            raise APIError(response.json()['error'])
+
+    def post(self, route, params):
+        response = requests.post(self.url + route, json=params)
+        if response.ok:
+            return response.json()
+        else:
+            raise APIError(response.json()['error'])
+

client/user_interface.py

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+from pathlib import Path
+from api import SubRosaAPI, APIError
+from datetime import datetime
+import sys
+sys.path.insert(0, ".")
+from encryption import PrivateKey, PublicKey
+
+class SubRosaUI:
+    """A user interface to the SubRosa chat system.
+    """
+    def __init__(self, private_key_file, url):
+        self.api = SubRosaAPI(url)
+        if Path(private_key_file).exists():
+            self.private_key = PrivateKey.load(private_key_file)
+        else:
+            self.private_key = PrivateKey.generate()
+            self.private_key.save(private_key_file)
+        self.public_key = self.private_key.get_public_key()
+
+    def run(self, username):
+        """Runs the client UI.
+        """
+        self.username = username
+        self.user = self.get_or_create_user(username)
+        print("Welcome to SubRosa.")
+        while True:
+            choice = self.choose_action_from_menu()
+            if choice == 'VIEW':
+                self.show_messages()
+            elif choice == 'SEND':
+                self.send_message()
+            print("=" * 80)
+
+    def get_or_create_user(self, username):
+        """Gets user info from the server, or creates the user. 
+        If the user already exists, checks that our public key matches
+        the server's public key for the user. 
+        """
+        try:
+            user = self.api.get_user(username)
+            if user['public_key'] != str(self.public_key):
+                raise ValueError(f"Invalid key for {username}")
+        except APIError:
+            user = self.api.create_user(username, str(self.public_key))
+        return user
+
+    def choose_action_from_menu(self):
+        """Gets a choice from the user. 
+        """
+        print("What would you like to do?")
+        print("1. See messages")
+        print("2. Send a message")
+        while True:
+            choice = input("> ").strip()
+            if choice == '1':
+                return 'VIEW'
+            elif choice == '2': 
+                return 'SEND'
+
+    def show_messages(self):
+        """Fetches all messages and displays them. 
+        Note: The messages arrive from the server encrypted.
+        """
+        messages = self.api.get_messages(self.username)['messages']
+        if messages:
+            for i, message in enumerate(messages):
+                print('-' * 80)
+                print(f"{i}. From {message['sender']}:")
+                print(message['ciphertext'])
+        else:
+            print(f"No messages for {self.username}.")
+
+    def send_message(self):
+        """Sends a message.
+        """
+        try:
+            recipient_name = input("Username of recipient: ").strip()
+            recipient = self.api.get_user(recipient_name)
+        except APIError:
+            print(f"No user named {recipient_name}.")
+            return
+        plaintext = input("Message: ")
+        print('-' * 80)
+        print(f"Sorry, couldn't send a message to {recipient_name}; this method isn't implemented yet.")
+
+    def get_current_time(self):
+        return datetime.utcnow().isoformat()
+
+def main():
+    from argparse import ArgumentParser
+    parser = ArgumentParser()
+    parser.add_argument("username", help="Existing or new username.")
+    parser.add_argument("-k", "--key", 
+        default="subrosa_private_key.pem", 
+        help="Private key file. Will be created if it does not exist."
+    )
+    parser.add_argument("-s", "--server-url", 
+        default="http://subrosa.makingwithcode.org",
+        help='Server URL. Use "http://127.0.0.1:5000" for a local server.'
+    )
+    args = parser.parse_args()
+    ui = SubRosaUI(args.key, args.server_url)
+    ui.run(args.username)
+
+if __name__ == '__main__':
+    main()

encryption.py

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+# This module provides higher-level wrappers around cryptography, 
+# handling intermediate steps and selecting parameters. This module
+# also allows users to work with strings instead of bytes, as users
+# will not yet have learned about encoding and decoding strings. 
+
+# NOTE: DO NOT USE THESE CLASSES IN SERIOUS APPLICATIONS.
+
+from cryptography.hazmat.primitives.asymmetric import rsa, padding
+from cryptography.hazmat.primitives import serialization, hashes
+from cryptography.exceptions import InvalidSignature
+from base64 import b64encode, b64decode
+from pathlib import Path
+
+PUBLIC_EXPONENT = 65537
+KEY_SIZE = 2048
+
+class PrivateKey:
+
+    @classmethod
+    def load(cls, pem):
+        """Loads an existing private key.
+        Pem may be a bytes or a string representation of the PEM-formatted key, 
+        or a path to a pem file. 
+        """
+        if isinstance(pem, bytes):
+            key = serialization.load_pem_private_key(pem, password=None)
+        elif isinstance(pem, str) and pem.startswith("-----BEGIN RSA PRIVATE KEY-----"):
+            key = serialization.load_pem_private_key(pem.encode('ascii'), password=None)
+        elif isinstance(pem, (str, Path)):
+            with open(pem, 'rb') as key_file:
+                key = serialization.load_pem_private_key(
+                    key_file.read(), 
+                    password=None
+                )
+        else:
+            raise TypeError("PrivateKey.load requires pem bytes or a file path")
+        return PrivateKey(key)
+
+    @classmethod
+    def generate(cls):
+        "Generates a new private key."
+        key = rsa.generate_private_key(
+            public_exponent=PUBLIC_EXPONENT,
+            key_size=KEY_SIZE,
+        )
+        return PrivateKey(key)
+
+    def __init__(self, key):
+        if not isinstance(key, rsa.RSAPrivateKey):
+            err = (
+                "PrivateKey is initialized with a rsa.RSAPrivateKey. " + 
+                "You probably want to use PrivateKey.load or PrivateKey.generate instead."
+            )
+            raise ValueError(err)
+        self.key = key
+
+    def __str__(self):
+        "Returns a string representation of the key in PEM format"
+        return self.key.private_bytes(
+            encoding=serialization.Encoding.PEM,
+            format=serialization.PrivateFormat.TraditionalOpenSSL,
+            encryption_algorithm=serialization.NoEncryption()
+        ).decode('utf8').strip()
+
+    def __repr__(self):
+        return "<PrivateKey>"
+
+    def save(self, filepath):
+        "Saves the key as a pem file"
+        Path(filepath).write_text(str(self))
+
+    def get_public_key(self):
+        "Gets the matching public key."
+        return PublicKey(self.key.public_key())
+
+    def sign(self, message):
+        """Create an encrypted signature of the message. 
+        Anyone with the public key can verify that the signer had the matching 
+        private key.
+        """
+        message_bytes = message.encode('utf8')
+        signature = self.key.sign(
+            message_bytes,
+            padding.PSS(
+                mgf=padding.MGF1(hashes.SHA256()),
+                salt_length=padding.PSS.MAX_LENGTH
+            ),
+            hashes.SHA256()
+        )
+        return b64encode(signature).decode('ascii')
+
+    def decrypt(self, ciphertext):
+        """Decrypts a message encrypted with the matching PublicKey.
+        """
+        ciphertext_bytes = b64decode(ciphertext.encode('ascii'))
+        plaintext = self.key.decrypt(
+            ciphertext_bytes,
+            padding.OAEP(
+                mgf=padding.MGF1(algorithm=hashes.SHA256()),
+                algorithm=hashes.SHA256(),
+                label=None
+            )
+        )
+        return plaintext.decode('utf8')
+
+class PublicKey:
+
+    @classmethod
+    def load(self, pem):
+        """Loads an existing public key.
+        Pem may be a bytes or a string representation of the PEM-formatted key, 
+        or a path to a pem file. 
+        """
+        if isinstance(pem, bytes):
+            key = serialization.load_pem_public_key(pem)
+        elif isinstance(pem, str) and pem.startswith("-----BEGIN PUBLIC KEY-----"):
+            key = serialization.load_pem_public_key(pem.encode('ascii'))
+        elif isinstance(pem, (str, Path)):
+            with open(pem, 'rb') as key_file:
+                key = serialization.load_pem_public_key(key_file.read())
+        else:
+            raise TypeError("PublicKey.load requires pem bytes or a file path")
+        return PublicKey(key)
+
+    def __init__(self, key):
+        self.key = key
+
+    def __str__(self):
+        "Returns a string representation of the key in PEM format"
+        return self.key.public_bytes(
+            encoding=serialization.Encoding.PEM,
+            format=serialization.PublicFormat.SubjectPublicKeyInfo
+        ).decode('utf8').strip()
+
+    def __repr__(self):
+        return "<PublicKey>"
+
+    def save(self, filepath):
+        """Saves this key to a file in PEM format.
+        """
+        Path(filepath).write_text(str(self))
+
+    def verify_signature(self, message, signature):
+        """Verifies that `message` was signed using the matching private key.
+        """
+        message_bytes = message.encode('utf8')
+        signature_bytes = b64decode(signature.encode('ascii'))
+        self.key.verify(
+            signature_bytes,
+            message_bytes,
+            padding.PSS(
+                mgf=padding.MGF1(hashes.SHA256()),
+                salt_length=padding.PSS.MAX_LENGTH
+            ),
+            hashes.SHA256()
+        )
+
+    def encrypt(self, message):
+        """Encrypts a message so it can be decrypted with the matching PrivateKey. 
+        If encryption fails, your message is probably too long. 
+        """
+        message_bytes = message.encode('utf8')
+        ciphertext = self.key.encrypt(
+            message_bytes,
+            padding.OAEP(
+                mgf=padding.MGF1(algorithm=hashes.SHA256()),
+                algorithm=hashes.SHA256(),
+                label=None
+            )
+        )
+        return b64encode(ciphertext).decode('ascii')

poetry.lock

@@ -0,0 +1,443 @@
+# This file is automatically @generated by Poetry 2.0.0 and should not be changed by hand.
+
+[[package]]
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+description = "ASGI specs, helper code, and adapters"
+optional = false
+python-versions = ">=3.8"
+groups = ["main"]
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+]
+
+[package.dependencies]
+typing-extensions = {version = ">=4", markers = "python_version < \"3.11\""}
+
+[package.extras]
+tests = ["mypy (>=0.800)", "pytest", "pytest-asyncio"]
+
+[[package]]
+name = "certifi"
+version = "2024.12.14"
+description = "Python package for providing Mozilla's CA Bundle."
+optional = false
+python-versions = ">=3.6"
+groups = ["main"]
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+]
+
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+version = "1.17.1"
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+    {file = "tzdata-2024.2.tar.gz", hash = "sha256:7d85cc416e9382e69095b7bdf4afd9e3880418a2413feec7069d533d6b4e31cc"},
+]
+
+[[package]]
+name = "urllib3"
+version = "2.3.0"
+description = "HTTP library with thread-safe connection pooling, file post, and more."
+optional = false
+python-versions = ">=3.9"
+groups = ["main"]
+files = [
+    {file = "urllib3-2.3.0-py3-none-any.whl", hash = "sha256:1cee9ad369867bfdbbb48b7dd50374c0967a0bb7710050facf0dd6911440e3df"},
+    {file = "urllib3-2.3.0.tar.gz", hash = "sha256:f8c5449b3cf0861679ce7e0503c7b44b5ec981bec0d1d3795a07f1ba96f0204d"},
+]
+
+[package.extras]
+brotli = ["brotli (>=1.0.9)", "brotlicffi (>=0.8.0)"]
+h2 = ["h2 (>=4,<5)"]
+socks = ["pysocks (>=1.5.6,!=1.5.7,<2.0)"]
+zstd = ["zstandard (>=0.18.0)"]
+
+[metadata]
+lock-version = "2.1"
+python-versions = ">=3.10,<4.0"
+content-hash = "74698516f4e2de40b2c6421f402f63fdd66f0ec69b29dc52cbca86e324408270"

pyproject.toml

@@ -0,0 +1,23 @@
+[project]
+name = "lab-subrosa"
+version = "0.1.0"
+description = ""
+authors = [
+    {name = "Chris Proctor",email = "chris@chrisproctor.net"}
+]
+license = {text = "MIT"}
+readme = "README.md"
+requires-python = ">=3.10,<4.0"
+dependencies = [
+    "django-banjo (>=0.9.1,<0.10.0)",
+    "cryptography (>=44.0.0,<45.0.0)",
+    "requests (>=2.32.3,<3.0.0)"
+]
+
+
+[build-system]
+requires = ["poetry-core>=2.0.0,<3.0.0"]
+build-backend = "poetry.core.masonry.api"
+
+[tool.poetry]
+package-mode = false

server/app/models.py

@@ -0,0 +1,29 @@
+from banjo.models import (
+    Model, 
+    StringField, 
+    ForeignKey,
+    BooleanField,
+)
+
+class User(Model):
+    name = StringField(unique=True)
+    public_key = StringField()
+
+    def to_dict(self):
+        return {
+            'name': self.name,
+            'public_key': self.public_key,
+        }
+
+class Message(Model):
+    sender = ForeignKey(User, related_name="messages_sent")
+    recipient = ForeignKey(User, related_name="messages_received")
+    ciphertext = StringField()
+    read = BooleanField()
+
+    def to_dict(self):
+        return {
+            'sender': self.sender.name,
+            'recipient': self.recipient.name, 
+            'ciphertext': self.ciphertext,
+        }

server/app/views.py

@@ -0,0 +1,95 @@
+from banjo.urls import route_get, route_post
+from app.models import User, Message
+from banjo.http import NotFound, NotAllowed
+from datetime import datetime
+from cryptography.exceptions import InvalidSignature
+import sys
+sys.path.insert(0, "..")
+from encryption import PrivateKey, PublicKey
+
+def get_or_create_admin():
+    if not User.objects.filter(name='subrosa_admin').exists():
+        private_key = PrivateKey.generate()
+        public_key = private_key.get_public_key()
+        admin = User(name='subrosa_admin', public_key=str(public_key))
+        admin.save()
+    return User.objects.get(name='subrosa_admin')
+
+@route_post("users/new", args={'name': str, 'public_key': str})
+def create_user(params):
+    "Creates a new user"
+    admin = get_or_create_admin()
+    try:
+        public_key = PublicKey.load(params['public_key'])
+    except (ValueError, FileNotFoundError):
+        raise NotAllowed("Invalid public key")
+    try:
+        new_user = User.from_dict(params)
+        new_user.save()
+        welcome = "Welcome to SubRosa! Please be a good community member."
+        message = Message(
+            sender=admin, 
+            recipient=new_user,
+            ciphertext=public_key.encrypt(welcome)
+        )
+        message.save()
+        return new_user.to_dict()
+    except:
+        raise NotAllowed(f"Username {params['name']} is already in use.")
+
+@route_get("users", args={'name': str})
+def get_user(params):
+    "Get a user's public key"
+    try:
+        user = User.objects.get(name=params['name'])
+        return user.to_dict()
+    except User.DoesNotExist:
+        raise NotFound(f"There is no user named {params['name']}")
+
+@route_get("messages", args={'name': str})
+def get_messages(params):
+    "Return all the messages for a user"
+    try:
+        recipient = User.objects.get(name=params['name'])
+    except User.DoesNotExist:
+        raise NotFound(f"There is no user named {params['name']}")
+    messages = Message.objects.filter(recipient=recipient)
+    return {'messages': [m.to_dict() for m in messages]}
+
+@route_get("messages/send", args={'sender': str, 'recipient': str, 'ciphertext': str,
+        'time_sent': str, 'time_sent_signature': str})
+def send_message(params):
+    """Securely sends an encrypted message from `sender` to `recipient`
+    Sender and recipient should be recognized usernames. 
+    Time sent should be the time the message was sent in isoformat.
+    Auth should be the time sent, encrypted with the sender's private key.
+    The ciphertext should be encrypted with the recipient's public key.
+    """
+    try:
+        sender = User.objects.get(name=params['sender'])
+        recipient = User.objects.get(name=params['recipient'])
+    except User.DoesNotExist:
+        raise NotFound(f"User not found.")
+    try: 
+        time_sent = datetime.fromisoformat(params['time_sent'])
+    except ValueError:
+        raise NotAllowed(f"Time sent ({params['time_sent']}) must be in isoformat")
+    now = datetime.utcnow()
+    if (now - time_sent).seconds > 10:
+        raise NotAllowed(f"The message is too old. Time sent must be within ten seconds")
+    sender_public_key = PublicKey.load(sender.public_key)
+    try:
+        sender_public_key.verify_signature(params['time_sent'], params['time_sent_signature'])
+    except InvalidSignature:
+        raise NotAllowed("Invalid signature.")
+    message = Message(
+        sender=sender,
+        recipient=recipient,
+        ciphertext=params['ciphertext'],
+    )
+    message.save()
+    return message.to_dict()
+
+        
+
+

subrosa_analysis.md

@@ -0,0 +1,38 @@
+# Sub Rosa Analysis 
+
+## Checkpoint 1
+
+Decrypt the message you received from the Sub Rosa administrator. 
+Include the code you used to decrypt it. What does the message say?
+
+## Checkpoint 2
+
+Once you have a fully-working client and server for encrypted chat, let's
+analyze potential vulnerabilities of the system. Answer the following
+questions:
+
+1. When you interact with the server at `https://subrosa.makingwithcode.org`,
+   you have no way of knowing what code is running. If the people running
+   the server are dishonest, is it possible for them to read your encrypted
+   messages? If so, explain how. If not, explain why not.
+
+
+2. Is it possible to impersonate another user, sending messages in their name?
+   If so, explain how--or demonstrate this with code. If not, explain why not.
+
+
+3. You can use a signature (a message and its encrypted version) to prove you
+   have a private key, without sharing the key itself. After you send someone
+   a signature, what stops them from using the same signature to later
+   impersonate you?
+
+
+4. On most websites, you can reset your password if you forget it, via a link
+   sent to your email or a code sent to your phone. If you lose your private
+   key, would it be possible to recover your messages?
+
+
+5. Even if you can't read other peoples' messages, you can see the sender and the
+   recipient for each message. Is this a big deal? Could the server be redesigned
+   so that the sender and the recipient are also encrypted?
+