Some PGP advancement

config.example.yml

@@ -17,3 +17,7 @@ apps:
     password: "pw1"
   app2@localhost:
     password: "pw2"
+
+gpg:
+  home: "/home/user/.gnupg"
+  passphrase: "phrase"

proxy.py

@@ -4,13 +4,22 @@ import base64
 import socket
 import yaml
 import signal
+from email import message_from_bytes
 from email.parser import BytesParser
 from email.policy import default
+from email.message import EmailMessage
+from email.mime.multipart import MIMEMultipart
+from email.mime.text import MIMEText
+from email.mime.base import MIMEBase
+from email.encoders import encode_base64
 from aiosmtpd.controller import Controller
-from aiosmtpd.smtp import  AuthResult
+from aiosmtpd.smtp import AuthResult, Envelope, Session
+import gnupg
 import sys
 from watchdog.observers import Observer
 from watchdog.events import FileSystemEventHandler
+import requests
+
 
 # ---------------------------
 # Load Configuration
@@ -66,6 +75,7 @@ def setup_logging():
 # Setup global logger
 logger = setup_logging()
 
+
 # ---------------------------
 # Watchdog for Configuration Reload
 # ---------------------------
@@ -100,7 +110,14 @@ SMTP_PASSWORD = config["smtp_server"]["password"]
 SMTP_FROM_NAME = config["smtp_server"]["from_name"]
 SMTP_FROM_EMAIL = config["smtp_server"]["from_email"]
 
-app_credentials = config["apps"]  # Allowed users' credentials
+
+APP_CREDENTIALS = config["apps"]  # Allowed users' credentials
+PASSPHRASE = config["gpg"]["passphrase"]
+
+gpg = gnupg.GPG(gnupghome=config["gpg"]["home"])
+gpg.encoding = "utf-8"
+
+KEYSERVER_URL = "https://keys.openpgp.org/vks/v1/by-email/"
 
 
 # ---------------------------
@@ -112,7 +129,7 @@ class EmailAuthenticator:
     """
 
     def __init__(self):
-        self.app_credentials = app_credentials
+        self.APP_CREDENTIALS = APP_CREDENTIALS
 
     async def __call__(self, server, session, envelope, mechanism, auth_data):
         fail_nothandled = AuthResult(success=False, handled=False)
@@ -137,11 +154,16 @@ class EmailAuthenticator:
                     return fail_nothandled
                 username, password = decoded.split("\x00")
 
-            if username in self.app_credentials and self.app_credentials[username]["password"] == password:
+            if (
+                username in self.APP_CREDENTIALS
+                and self.APP_CREDENTIALS[username]["password"] == password
+            ):
                 logger.info(f"✅ Authentication successful for {username}")
                 return AuthResult(success=True)
             else:
-                logger.error(f"❌ Authentication failed for {username}: Incorrect password")
+                logger.error(
+                    f"❌ Authentication failed for {username}: Incorrect password"
+                )
                 return fail_nothandled
 
         except Exception as e:
@@ -150,15 +172,15 @@ class EmailAuthenticator:
 
 
 # ---------------------------
-# EmailLoggingProxy Class
+# EmailProxy Class
 # ---------------------------
-class EmailLoggingProxy:
+class EmailProxy:
     """
     Handler for incoming emails that logs the data, performs authentication,
     rewrites the 'From' header, and forwards the email via the specified SMTP server.
     """
 
-    async def handle_EHLO(self, server, session, envelope, hostname):
+    async def handle_EHLO(self, server, session: Session, envelope: Envelope, hostname):
         """Handle the EHLO command and advertise AUTH support."""
         session.host_name = hostname
         return (
@@ -170,7 +192,7 @@ class EmailLoggingProxy:
             "250 HELP"
         )
 
-    async def handle_DATA(self, server, session, envelope):
+    async def handle_DATA(self, server, session: Session, envelope: Envelope):
         """
         Handle the DATA command, log the email, modify the From header,
         and forward the email via the specified SMTP server.
@@ -184,29 +206,193 @@ class EmailLoggingProxy:
         # Log the email content
         logger.debug(f"Mail data:\n{data.decode('utf-8', errors='replace')}")
 
-        # Validate sender against allowed app credentials
-        if mailfrom not in app_credentials:
-            logger.error(f"🚫 Unauthorized sender: {mailfrom}")
-            return "550 Unauthorized sender"
-
         # Parse the email
         msg = BytesParser(policy=default).parsebytes(data)
 
         # Modify the "From" header with the configuration details
         msg.replace_header("From", f"{SMTP_FROM_NAME} <{SMTP_FROM_EMAIL}>")
 
-        # Forward the email via the specified SMTP server
+        encrypted_recipients = []
-        try:
+        unencrypted_recipients = []
-            logger.info(f"📤 Forwarding email to {rcpttos} via SMTP server...")
+
-            with smtplib.SMTP(SMTP_SERVER_HOST, SMTP_SERVER_PORT) as smtp_server:
+        for recipient in rcpttos:
-                smtp_server.starttls()  # Upgrade connection to TLS
+            if self.fetch_pgp_key(recipient):
-                smtp_server.login(SMTP_USER, SMTP_PASSWORD)
+                encrypted_recipients.append(recipient)
-                smtp_server.sendmail(SMTP_FROM_EMAIL, rcpttos, msg.as_bytes())
+            else:
-            logger.info(f"✅ Email successfully forwarded to {rcpttos}")
+                unencrypted_recipients.append(recipient)
+
+        bcc_recipients = []
+        if "Bcc" in msg:
+            bcc_recipients = msg["Bcc"].split(",")
+            del msg["Bcc"]
+
+        if encrypted_recipients:
+            encrypted_msg = self.encrypt_mime_email(msg, encrypted_recipients)
+            if encrypted_msg:
+                self.send_email(encrypted_msg, encrypted_recipients)
+
+        if unencrypted_recipients:
+            plaintext_msg = self.add_unencrypted_warning(msg)
+            self.send_email(plaintext_msg, unencrypted_recipients)
+
+        # Send separate emails to each BCC recipient for privacy
+        for bcc in bcc_recipients:
+            if bcc in encrypted_recipients:
+                self.send_email(self.encrypt_mime_email(msg, [bcc]), [bcc])
+            else:
+                self.send_email(self.add_unencrypted_warning(msg), [bcc])
+
         return "250 OK"
+
+    def fetch_pgp_key(self, email):
+        """Checks if a PGP key exists locally or fetches it from the keyserver."""
+
+        # Check if the key exists locally
+        keys = gpg.list_keys(keys=email)
+        if keys:
+            logger.info(f"✅ PGP key for {email} found locally.")
+            return True  # Key exists locally
+
+        # Key does not exist locally, so try fetching from the keyserver
+        logger.info(f"🔍 Looking up PGP key for {email} on keyserver...")
+
+        # Request the key from the keyserver API
+        keyserver_url = f"{KEYSERVER_URL}{email}"
+        try:
+            response = requests.get(keyserver_url)
+
+            if response.status_code == 200:
+                key_data = response.text
+                logger.info(
+                    f"✅ Successfully retrieved PGP key for {email} from keyserver."
+                )
+
+                # Import the key into GPG
+                import_result = gpg.import_keys(key_data)
+
+                if import_result.count > 0:
+                    logger.info(
+                        f"✅ PGP key for {email} successfully imported into GPG."
+                    )
+                    return True
+                else:
+                    logger.warning(f"❌ Failed to import PGP key for {email}.")
+                    return False
+            else:
+                logger.warning(
+                    f"❌ No PGP key found for {email}. HTTP status code: {response.status_code}"
+                )
+                return False
+        except requests.exceptions.RequestException as e:
+            logger.error(f"❌ Error while contacting keyserver: {e}")
+            return False
+
+    def encrypt_mime_email(self, msg, recipients):
+        """Encrypts a full email as PGP/MIME with multiple recipients and hides the subject."""
+        original_subject = msg["Subject"]
+        msg.replace_header("Subject", "...")
+
+        
+        # Convert email to MIME
+        mime_msg = MIMEMultipart()
+        mime_msg["Subject"] = "..."
+        mime_msg["From"] = msg["From"]
+        mime_msg["To"] = ", ".join(recipients)
+
+        # Add original subject inside encrypted content
+        text_part = MIMEText(f"Subject: {original_subject}\n\n{msg.as_string()}")
+        mime_msg.attach(text_part)
+
+        # Encrypt with all recipient keys
+        encrypted_data = gpg.encrypt(
+            mime_msg.as_string(),
+            recipients=recipients,
+            sign=SMTP_FROM_EMAIL,
+            always_trust=True,
+            passphrase=PASSPHRASE,
+        )
+
+        if not encrypted_data.ok:
+            logger.error(f"❌ Encryption failed: {encrypted_data.stderr}")
+            return None
+
+        # Create PGP/MIME encrypted email
+        encrypted_email = MIMEMultipart(
+            "encrypted", protocol="application/pgp-encrypted"
+        )
+        encrypted_email["Subject"] = "Encrypted Message"
+        encrypted_email["From"] = msg["From"]
+        encrypted_email["To"] = ", ".join(recipients)
+
+        # PGP version header
+        pgp_header = MIMEBase("application", "pgp-encrypted")
+        pgp_header.add_header("Content-Description", "PGP/MIME Versions Header")
+        pgp_header.set_payload("Version: 1\r\n")
+        encrypted_email.attach(pgp_header)
+
+        # Encrypted email payload
+        encrypted_part = MIMEBase("application", "octet-stream")
+        encrypted_part.set_payload(str(encrypted_data))
+        encrypted_part.add_header(
+            "Content-Disposition", "inline", filename="encrypted.asc"
+        )
+        encrypted_email.attach(encrypted_part)
+
+        return encrypted_email
+
+    def add_unencrypted_warning(self, msg):
+        """Adds a warning footer to unencrypted emails for both plain-text and HTML bodies."""
+        warning_text = (
+            "\n\n⚠️ This email was sent without end-to-end encryption.\n"
+            "This mail server supports automatic PGP encryption.\n"
+            "Consider setting up a PGP key and publishing it to a keyserver (e.g., keys.openpgp.org)."
+        )
+
+        # For multipart emails (text/plain + text/html)
+        if msg.is_multipart():
+            for part in msg.walk():
+                # Check if the part is plain text
+                if part.get_content_type() == "text/plain":
+                    part.set_payload(part.get_payload() + warning_text)
+                # Check if the part is HTML text
+                elif part.get_content_type() == "text/html":
+                    html_warning = (
+                        f"<p><strong>⚠️ This email was sent without end-to-end encryption.</strong><br>"
+                        f"This mail server supports automatic PGP encryption.<br>"
+                        f"Consider setting up a PGP key and publishing it to a keyserver "
+                        f"(e.g., keys.openpgp.org).</p>"
+                    )
+                    part.set_payload(part.get_payload() + html_warning)
+                    part.replace_header(
+                        "Content-Transfer-Encoding", "quoted-printable"
+                    )  # Ensure HTML part is encoded correctly
+        else:
+            # If it's a non-multipart message (either plain-text or HTML only)
+            if msg.get_content_type() == "text/plain":
+                msg.set_payload(msg.get_payload() + warning_text)
+            elif msg.get_content_type() == "text/html":
+                html_warning = (
+                    f"<p><strong>⚠️ This email was sent without end-to-end encryption.</strong><br>"
+                    f"This mail server supports automatic PGP encryption.<br>"
+                    f"Consider setting up a PGP key and publishing it to a keyserver "
+                    f"(e.g., keys.openpgp.org).</p>"
+                )
+                msg.set_payload(msg.get_payload() + html_warning)
+                msg.replace_header("Content-Transfer-Encoding", "quoted-printable")
+
+        return msg
+
+    def send_email(self, msg, recipients):
+        """Sends an email via SMTP, ensuring BCC recipients remain private."""
+        try:
+            logger.info(f"📤 Sending email to {recipients} via SMTP...")
+            with smtplib.SMTP(SMTP_SERVER_HOST, SMTP_SERVER_PORT) as smtp_server:
+                smtp_server.starttls()
+                smtp_server.login(SMTP_USER, SMTP_PASSWORD)
+                smtp_server.sendmail(SMTP_FROM_EMAIL, recipients, msg.as_bytes())
+            logger.info(f"✅ Email successfully sent to {recipients}")
         except Exception as e:
             logger.error(f"❌ Failed to send email: {e}")
-            return "550 Internal server error"
 
 
 # ---------------------------
@@ -223,8 +409,14 @@ def run_proxy():
         authenticator = EmailAuthenticator()
 
         # Create the SMTP instance and pass it as handler to the Controller
-        smtp_handler = EmailLoggingProxy()
+        smtp_handler = EmailProxy()
-        controller = Controller(smtp_handler, hostname=PROXY_HOST, port=PROXY_PORT, authenticator=authenticator, auth_require_tls=False)
+        controller = Controller(
+            smtp_handler,
+            hostname=PROXY_HOST,
+            port=PROXY_PORT,
+            authenticator=authenticator,
+            auth_require_tls=False,
+        )
 
         # Start the config file watcher in a separate thread
         config_watcher = Observer()

requirements.txt

@@ -1,3 +1,5 @@
 aiosmtpd==1.4.6
 PyYAML==6.0.2
 watchdog==6.0.0
+python-gnupg==0.5.4
+requests==2.32.3