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fix: use SMTP_SSL for port 465, STARTTLS for 587

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Auto-detect SSL vs STARTTLS based on port number instead of always
using SMTP + starttls(), which times out on port 465 (implicit SSL).

Authored by: Jack Levy
This commit is contained in:
Jack Levy
2026-03-14 23:18:32 -04:00
parent f6770b16be
commit 4308404cca
2 changed files with 14 additions and 4 deletions
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9
backend/app/api/notifications.py
View File

@@ -216,8 +216,13 @@ async def test_email(
msg["From"] = from_addr msg["From"] = from_addr
msg["To"] = email_addr msg["To"] = email_addr
with smtplib.SMTP(app_settings.SMTP_HOST, app_settings.SMTP_PORT, timeout=10) as s: use_ssl = app_settings.SMTP_PORT == 465
if app_settings.SMTP_STARTTLS: if use_ssl:
ctx = smtplib.SMTP_SSL(app_settings.SMTP_HOST, app_settings.SMTP_PORT, timeout=10)
else:
ctx = smtplib.SMTP(app_settings.SMTP_HOST, app_settings.SMTP_PORT, timeout=10)
with ctx as s:
if not use_ssl and app_settings.SMTP_STARTTLS:
s.starttls() s.starttls()
if app_settings.SMTP_USER: if app_settings.SMTP_USER:
s.login(app_settings.SMTP_USER, app_settings.SMTP_PASSWORD) s.login(app_settings.SMTP_USER, app_settings.SMTP_PASSWORD)

9
backend/app/workers/notification_dispatcher.py
View File

@@ -339,8 +339,13 @@ def _send_email(
msg["List-Unsubscribe-Post"] = "List-Unsubscribe=One-Click" msg["List-Unsubscribe-Post"] = "List-Unsubscribe=One-Click"
msg.attach(MIMEText(body, "plain", "utf-8")) msg.attach(MIMEText(body, "plain", "utf-8"))
with smtplib.SMTP(app_settings.SMTP_HOST, app_settings.SMTP_PORT, timeout=10) as s: use_ssl = app_settings.SMTP_PORT == 465
if app_settings.SMTP_STARTTLS: if use_ssl:
smtp_ctx = smtplib.SMTP_SSL(app_settings.SMTP_HOST, app_settings.SMTP_PORT, timeout=10)
else:
smtp_ctx = smtplib.SMTP(app_settings.SMTP_HOST, app_settings.SMTP_PORT, timeout=10)
with smtp_ctx as s:
if not use_ssl and app_settings.SMTP_STARTTLS:
s.starttls() s.starttls()
if app_settings.SMTP_USER: if app_settings.SMTP_USER:
s.login(app_settings.SMTP_USER, app_settings.SMTP_PASSWORD) s.login(app_settings.SMTP_USER, app_settings.SMTP_PASSWORD)