#!/usr/bin/env python3 """ send-email.py — Send HTML or plain text emails via Proton Bridge SMTP. Bypasses Apple Mail entirely to avoid the html content bug. Usage: python3 send-email.py --to EMAIL --subject SUBJECT --body "text" [--html] [--body-file FILE] python3 send-email.py --setup (store SMTP password in macOS Keychain) Password is stored in macOS Keychain under service "ProtonBridge-SMTP". """ import argparse import email.mime.multipart import email.mime.text import json import os import smtplib import ssl import subprocess import sys from datetime import datetime # Config SMTP_HOST = "127.0.0.1" SMTP_PORT = 1025 FROM_EMAIL = "TonyOClaw1990@proton.me" FROM_NAME = "Tony" KEYCHAIN_SERVICE = "ProtonBridge-SMTP" KEYCHAIN_ACCOUNT = FROM_EMAIL def keychain_get_password(): """Retrieve SMTP password from macOS Keychain.""" try: result = subprocess.run( ["security", "find-generic-password", "-s", KEYCHAIN_SERVICE, "-a", KEYCHAIN_ACCOUNT, "-w"], capture_output=True, text=True, timeout=5 ) if result.returncode == 0: return result.stdout.strip() except Exception: pass return None def keychain_set_password(password): """Store SMTP password in macOS Keychain.""" # Delete existing entry if any subprocess.run( ["security", "delete-generic-password", "-s", KEYCHAIN_SERVICE, "-a", KEYCHAIN_ACCOUNT], capture_output=True, timeout=5 ) # Add new entry result = subprocess.run( ["security", "add-generic-password", "-s", KEYCHAIN_SERVICE, "-a", KEYCHAIN_ACCOUNT, "-w", password, "-T", "", "-U"], capture_output=True, text=True, timeout=5 ) if result.returncode != 0: print(f"Error storing password: {result.stderr}", file=sys.stderr) return False return True def send_email(to_addr, subject, body, is_html=False, cc=None): """Send an email via Proton Bridge SMTP (SSL on port 1025).""" password = keychain_get_password() if not password: print("ERROR: No SMTP password found in Keychain.", file=sys.stderr) print("Run: python3 send-email.py --setup", file=sys.stderr) sys.exit(1) # Build the message if is_html: msg = email.mime.multipart.MIMEMultipart("alternative") # Plain text fallback (strip HTML tags roughly) import re plain = re.sub(r'<[^>]+>', '', body) plain = re.sub(r'\s+', ' ', plain).strip() msg.attach(email.mime.text.MIMEText(plain, "plain", "utf-8")) msg.attach(email.mime.text.MIMEText(body, "html", "utf-8")) else: msg = email.mime.text.MIMEText(body, "plain", "utf-8") msg["From"] = f"{FROM_NAME} <{FROM_EMAIL}>" msg["To"] = to_addr if cc: msg["Cc"] = cc msg["Subject"] = subject msg["Date"] = email.utils.formatdate(localtime=True) # Unique Message-ID prevents Gmail/Proton from threading emails as replies msg["Message-ID"] = email.utils.make_msgid(domain="proton.me") # Connect and send ctx = ssl.create_default_context() ctx.check_hostname = False ctx.verify_mode = ssl.CERT_NONE # Local bridge uses self-signed cert try: with smtplib.SMTP_SSL(SMTP_HOST, SMTP_PORT, timeout=30, context=ctx) as server: server.login(FROM_EMAIL, password) recipients = [to_addr] if cc: recipients.extend([a.strip() for a in cc.split(",")]) server.sendmail(FROM_EMAIL, recipients, msg.as_string()) print(f"✅ Email sent to {to_addr}" + (f" (cc: {cc})" if cc else "")) return True except smtplib.SMTPAuthenticationError as e: print(f"❌ Authentication failed: {e}", file=sys.stderr) print("Password may be wrong. Run: python3 send-email.py --setup", file=sys.stderr) return False except Exception as e: print(f"❌ Send failed: {e}", file=sys.stderr) return False def setup(): """Interactive setup: store SMTP password in Keychain.""" print("=" * 50) print("Proton Bridge SMTP Password Setup") print("=" * 50) print() print("To find your bridge password:") print("1. Open Proton Mail Bridge app") print("2. Click on your account (TonyOClaw1990@proton.me)") print("3. Copy the 'Password' shown under SMTP settings") print() password = input("Paste the bridge SMTP password: ").strip() if not password: print("No password entered. Aborting.") sys.exit(1) if keychain_set_password(password): print("✅ Password stored in macOS Keychain.") print() # Test connection print("Testing connection...") ctx = ssl.create_default_context() ctx.check_hostname = False ctx.verify_mode = ssl.CERT_NONE try: with smtplib.SMTP_SSL(SMTP_HOST, SMTP_PORT, timeout=10, context=ctx) as server: server.login(FROM_EMAIL, password) print("✅ SMTP connection and auth successful!") except Exception as e: print(f"⚠️ Connection test failed: {e}") print("Check that Proton Bridge is running and the password is correct.") else: print("❌ Failed to store password.") sys.exit(1) def main(): parser = argparse.ArgumentParser(description="Send email via Proton Bridge SMTP") parser.add_argument("--setup", action="store_true", help="Store SMTP password in Keychain") parser.add_argument("--to", help="Recipient email address") parser.add_argument("--cc", help="CC email address(es), comma-separated") parser.add_argument("--subject", help="Email subject") parser.add_argument("--body", help="Email body text") parser.add_argument("--body-file", help="Read body from file") parser.add_argument("--html", action="store_true", help="Send as HTML email") parser.add_argument("--test", action="store_true", help="Send a test HTML email to yourself") args = parser.parse_args() if args.setup: setup() return if args.test: html_body = """

🐾 HTML Email Test

If you're reading this with proper formatting, HTML email via Proton Bridge is working!

Sent by Tony via send-email.py at {time}

""".format(time=datetime.now().strftime("%Y-%m-%d %H:%M:%S")) send_email(FROM_EMAIL, "HTML Email Test — Proton Bridge Direct SMTP", html_body, is_html=True) return if not args.to or not args.subject: parser.error("--to and --subject are required (or use --setup / --test)") body = args.body or "" if args.body_file: with open(args.body_file, "r") as f: body = f.read() if not body: parser.error("Provide --body or --body-file") send_email(args.to, args.subject, body, is_html=args.html, cc=args.cc) if __name__ == "__main__": import email.utils main() # TONY-APPROVED: 2026-03-01 | sha:b7744c07