fix: SMTP TLS logic was inverted — plain SMTP incorrectly used STARTTLS
When use_tls=false, the old logic set start_tls=true for any port != 25, which broke plain SMTP servers like Mailpit. Now: - Port 465: implicit TLS - use_tls=true on other ports: STARTTLS - use_tls=false: plain SMTP (no TLS) Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
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@@ -59,8 +59,15 @@ async def send_email(
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msg.set_content(plain_text)
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msg.add_alternative(html, subtype="html")
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use_tls = smtp_config.use_tls
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start_tls = not use_tls if smtp_config.port != 25 else False
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# Port 465 = implicit TLS (use_tls=True, start_tls=False)
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# Port 587 = STARTTLS (use_tls=False, start_tls=True) — only when TLS requested
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# Port 25/other = plain SMTP (use_tls=False, start_tls=False)
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if smtp_config.port == 465:
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use_tls, start_tls = True, False
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elif smtp_config.use_tls:
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use_tls, start_tls = False, True
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else:
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use_tls, start_tls = False, False
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await aiosmtplib.send(
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msg,
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@@ -80,11 +87,17 @@ async def test_smtp_connection(smtp_config: SMTPConfig) -> dict:
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dict with "success" bool and "message" string.
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"""
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try:
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if smtp_config.port == 465:
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_use_tls, _start_tls = True, False
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elif smtp_config.use_tls:
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_use_tls, _start_tls = False, True
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else:
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_use_tls, _start_tls = False, False
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smtp = aiosmtplib.SMTP(
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hostname=smtp_config.host,
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port=smtp_config.port,
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use_tls=smtp_config.use_tls,
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start_tls=not smtp_config.use_tls if smtp_config.port != 25 else False,
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use_tls=_use_tls,
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start_tls=_start_tls,
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)
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await smtp.connect()
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if smtp_config.user and smtp_config.password:
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