@@ -2635,7 +2637,9 @@ async function initEmailAccountsSettings() {
el('eaf-imap-starttls').checked = !!p.imap.starttls;
el('eaf-smtp-host').value = p.smtp.host;
el('eaf-smtp-port').value = p.smtp.port;
+ el('eaf-smtp-security').value = p.smtp.security || ((parseInt(p.smtp.port || 465) === 587) ? 'starttls' : 'ssl');
});
+ el('eaf-smtp-security').value = _smtpSecurity(a);
// "Same as IMAP" toggle — hide the SMTP creds rows when on. The save
// handler copies the IMAP user/password into SMTP at submit time.
@@ -2659,6 +2663,7 @@ async function initEmailAccountsSettings() {
imap_starttls: el('eaf-imap-starttls').checked,
smtp_host: el('eaf-smtp-host').value.trim(),
smtp_port: parseInt(el('eaf-smtp-port').value) || 465,
+ smtp_security: el('eaf-smtp-security').value,
smtp_user: el('eaf-smtp-user').value.trim(),
};
if (el('eaf-imap-pass').value) body.imap_password = el('eaf-imap-pass').value;
@@ -3681,6 +3686,7 @@ async function initUnifiedIntegrations() {
};
const _providerOptions = Object.entries(PROVIDERS)
.map(([k, v]) => `
`).join('');
+ const _smtpSecurity = (acct) => acct?.smtp_security || ((parseInt(acct?.smtp_port || 465) === 587) ? 'starttls' : 'ssl');
formEl.innerHTML = `
${isEdit ? 'Edit' : 'Add'} Email Account
@@ -3698,6 +3704,7 @@ async function initUnifiedIntegrations() {
SMTP (Sending) — optional, leave blank for read-only
+
@@ -3824,6 +3831,7 @@ async function initUnifiedIntegrations() {
el('uf-imap-starttls').checked = !!p.imap.starttls;
el('uf-smtp-host').value = p.smtp.host;
el('uf-smtp-port').value = p.smtp.port;
+ el('uf-smtp-security').value = p.smtp.security || ((parseInt(p.smtp.port || 465) === 587) ? 'starttls' : 'ssl');
if (p.emailEx) {
el('uf-email-from').placeholder = p.emailEx;
el('uf-imap-user').placeholder = p.emailEx;
@@ -3849,6 +3857,7 @@ async function initUnifiedIntegrations() {
el('uf-imap-starttls').checked = existing.imap_starttls !== false;
el('uf-smtp-host').value = existing.smtp_host || '';
el('uf-smtp-port').value = existing.smtp_port || 465;
+ el('uf-smtp-security').value = _smtpSecurity(existing);
el('uf-smtp-user').value = existing.smtp_user || '';
el('uf-email-default').checked = !!existing.is_default;
// If the saved SMTP user matches the IMAP user, keep the "Same as
@@ -3860,6 +3869,7 @@ async function initUnifiedIntegrations() {
} else {
el('uf-imap-port').value = 993;
el('uf-smtp-port').value = 465;
+ el('uf-smtp-security').value = 'ssl';
}
el('uf-email-cancel').addEventListener('click', () => { formEl.style.display = 'none'; });
@@ -3895,6 +3905,7 @@ async function initUnifiedIntegrations() {
imap_starttls: el('uf-imap-starttls').checked,
smtp_host: el('uf-smtp-host').value.trim(),
smtp_port: parseInt(el('uf-smtp-port').value) || 465,
+ smtp_security: el('uf-smtp-security').value,
smtp_user: el('uf-smtp-user').value.trim(),
is_default: el('uf-email-default').checked,
};
diff --git a/tests/test_email_smtp_security.py b/tests/test_email_smtp_security.py
new file mode 100644
index 0000000..590a5e6
--- /dev/null
+++ b/tests/test_email_smtp_security.py
@@ -0,0 +1,105 @@
+import os
+import tempfile
+from pathlib import Path
+
+_tmp_data = Path(tempfile.mkdtemp(prefix="odysseus-email-smtp-test-"))
+os.environ.setdefault("DATA_DIR", str(_tmp_data))
+os.environ.setdefault("DATABASE_URL", f"sqlite:///{_tmp_data / 'app.db'}")
+
+from routes.email_helpers import _send_smtp_message
+
+
+class _FakeSMTP:
+ calls = []
+
+ def __init__(self, host, port, timeout=None):
+ self.host = host
+ self.port = port
+ self.timeout = timeout
+ self.starttls_called = False
+ _FakeSMTP.calls.append(("connect", self.__class__.__name__, host, port))
+
+ def __enter__(self):
+ return self
+
+ def __exit__(self, exc_type, exc, tb):
+ return False
+
+ def starttls(self):
+ self.starttls_called = True
+ _FakeSMTP.calls.append(("starttls", self.host, self.port))
+
+ def login(self, user, password):
+ _FakeSMTP.calls.append(("login", user, password))
+
+ def sendmail(self, from_addr, recipients, message):
+ _FakeSMTP.calls.append(("sendmail", from_addr, tuple(recipients), message, self.starttls_called))
+
+
+class _FakeSMTPSSL(_FakeSMTP):
+ pass
+
+
+def _cfg(security, port=2525):
+ return {
+ "smtp_host": "smtp.local",
+ "smtp_port": port,
+ "smtp_security": security,
+ "smtp_user": "user",
+ "smtp_password": "pw",
+ }
+
+
+def test_send_smtp_message_supports_plain_smtp(monkeypatch):
+ import routes.email_helpers as helpers
+
+ _FakeSMTP.calls = []
+ monkeypatch.setattr(helpers.smtplib, "SMTP", _FakeSMTP)
+ monkeypatch.setattr(helpers.smtplib, "SMTP_SSL", _FakeSMTPSSL)
+
+ _send_smtp_message(_cfg("none"), "from@example.com", ["to@example.com"], "hello")
+
+ assert _FakeSMTP.calls[0] == ("connect", "_FakeSMTP", "smtp.local", 2525)
+ assert not any(call[0] == "starttls" for call in _FakeSMTP.calls)
+ assert _FakeSMTP.calls[-1] == ("sendmail", "from@example.com", ("to@example.com",), "hello", False)
+
+
+def test_send_smtp_message_supports_explicit_starttls(monkeypatch):
+ import routes.email_helpers as helpers
+
+ _FakeSMTP.calls = []
+ monkeypatch.setattr(helpers.smtplib, "SMTP", _FakeSMTP)
+ monkeypatch.setattr(helpers.smtplib, "SMTP_SSL", _FakeSMTPSSL)
+
+ _send_smtp_message(_cfg("starttls", port=2525), "from@example.com", ["to@example.com"], "hello")
+
+ assert _FakeSMTP.calls[0] == ("connect", "_FakeSMTP", "smtp.local", 2525)
+ assert ("starttls", "smtp.local", 2525) in _FakeSMTP.calls
+ assert _FakeSMTP.calls[-1] == ("sendmail", "from@example.com", ("to@example.com",), "hello", True)
+
+
+def test_send_smtp_message_defaults_587_to_starttls(monkeypatch):
+ import routes.email_helpers as helpers
+
+ _FakeSMTP.calls = []
+ monkeypatch.setattr(helpers.smtplib, "SMTP", _FakeSMTP)
+ monkeypatch.setattr(helpers.smtplib, "SMTP_SSL", _FakeSMTPSSL)
+
+ cfg = _cfg("", port=587)
+ _send_smtp_message(cfg, "from@example.com", ["to@example.com"], "hello")
+
+ assert _FakeSMTP.calls[0] == ("connect", "_FakeSMTP", "smtp.local", 587)
+ assert ("starttls", "smtp.local", 587) in _FakeSMTP.calls
+
+
+def test_send_smtp_message_uses_ssl_when_configured(monkeypatch):
+ import routes.email_helpers as helpers
+
+ _FakeSMTP.calls = []
+ monkeypatch.setattr(helpers.smtplib, "SMTP", _FakeSMTP)
+ monkeypatch.setattr(helpers.smtplib, "SMTP_SSL", _FakeSMTPSSL)
+
+ _send_smtp_message(_cfg("ssl", port=465), "from@example.com", ["to@example.com"], "hello")
+
+ assert _FakeSMTP.calls[0] == ("connect", "_FakeSMTPSSL", "smtp.local", 465)
+ assert not any(call[0] == "starttls" for call in _FakeSMTP.calls)