feat(email): set Reply-To headers on confirmation and notification emails

- notify_parent: adds Reply-To set to the first CC (admin) address so
  parent replies to the completion confirmation reach the admin rather
  than re-entering the agent pipeline
- notify_admin / notify_registration_update: Reply-To = parent email
  was already wired through _send(); confirmed with new tests
- Mid-registration send_reply emails carry no Reply-To (verified by test)
- 5 new tests across TestNotifyParentReplyTo and TestNotifyAdminReplyTo;
  1 new test in TestSendReplyNoAdminReplyTo (174 passing, 0 failing)

https://claude.ai/code/session_014NynTjALA5TeP85mbr5ZA8

openspec/changes/email-reply-to-addresses/tasks.md

@@ -1,19 +1,19 @@
 ## 1. Confirmation Email Reply-To (Email Channel)
 
-- [ ] 1.1 Identify where the registration completion confirmation email is constructed in `src/` (email channel adapter / agent core)
+- [x] 1.1 Identify where the registration completion confirmation email is constructed in `src/` (email channel adapter / agent core)
-- [ ] 1.2 Add `Reply-To: spielgruppen@familien-verein.ch` header to the confirmation email only (not to mid-registration conversational emails)
+- [x] 1.2 Add `Reply-To: spielgruppen@familien-verein.ch` header to the confirmation email only (not to mid-registration conversational emails)
-- [ ] 1.3 Add a unit test verifying the `Reply-To` header is present on the confirmation email
+- [x] 1.3 Add a unit test verifying the `Reply-To` header is present on the confirmation email
-- [ ] 1.4 Add a unit test verifying mid-registration emails do NOT carry the admin `Reply-To` header
+- [x] 1.4 Add a unit test verifying mid-registration emails do NOT carry the admin `Reply-To` header
 
 ## 2. Notification Email Reply-To (Registration Notifications)
 
-- [ ] 2.1 Identify where registration notification emails are constructed and sent
+- [x] 2.1 Identify where registration notification emails are constructed and sent
-- [ ] 2.2 Set `Reply-To: <parent email>` header on all outgoing notification emails (indoor, outdoor, and both routing types)
+- [x] 2.2 Set `Reply-To: <parent email>` header on all outgoing notification emails (indoor, outdoor, and both routing types)
-- [ ] 2.3 Add a unit test verifying the `Reply-To` header equals the parent's email for indoor-only notification
+- [x] 2.3 Add a unit test verifying the `Reply-To` header equals the parent's email for indoor-only notification
-- [ ] 2.4 Add a unit test verifying the `Reply-To` header equals the parent's email for outdoor-only notification
+- [x] 2.4 Add a unit test verifying the `Reply-To` header equals the parent's email for outdoor-only notification
-- [ ] 2.5 Add a unit test verifying the `Reply-To` header equals the parent's email when both leaders are notified
+- [x] 2.5 Add a unit test verifying the `Reply-To` header equals the parent's email when both leaders are notified
 
 ## 3. Verification
 
-- [ ] 3.1 Run the full test suite and confirm all tests pass
+- [x] 3.1 Run the full test suite and confirm all tests pass
 - [ ] 3.2 Manually send a test registration through the email channel and verify reply routing behaves correctly

src/notifications/notifier.py

@@ -215,6 +215,8 @@ class AdminNotifier:
         msg_outer["From"] = self._from_email
         msg_outer["To"] = parent_email
         msg_outer["Subject"] = subject
+        if self._cc_emails:
+            msg_outer["Reply-To"] = self._cc_emails[0]
 
         msg_alt = MIMEMultipart("alternative")
         msg_alt.attach(MIMEText(text_body, "plain", "utf-8"))

tests/test_email_loop_prevention.py

@@ -1,10 +1,11 @@
-"""Tests for email loop prevention.
+"""Tests for email loop prevention and email channel reply headers.
 
-Covers three layers:
+Covers four areas:
 - detect_automated_message() — header-based bounce/automated sender detection
 - EmailAgent.handle_automated_message() — state tracking, one-shot admin alert
 - EmailAgent.process_message() — hard message-count cap (MAX_USER_MESSAGES)
 - AdminNotifier.notify_loop_escalation() — escalation email dispatch
+- EmailChannel.send_reply() — mid-registration emails must not carry admin Reply-To
 """
 
 import email
@@ -13,7 +14,7 @@ import json
 import pytest
 from unittest.mock import MagicMock, patch
 
-from src.channels.email_channel import detect_automated_message
+from src.channels.email_channel import detect_automated_message, EmailChannel
 from src.agent.core import EmailAgent, MAX_USER_MESSAGES
 from src.models.conversation import ConversationState, ChatMessage
 from src.notifications.notifier import AdminNotifier
@@ -650,3 +651,42 @@ class TestNotifyLoopEscalation:
         )
 
         mock_smtp_cls.assert_not_called()
+
+
+# ---------------------------------------------------------------------------
+# EmailChannel.send_reply — mid-registration emails must not have admin Reply-To
+# (task 1.4)
+# ---------------------------------------------------------------------------
+
+
+class TestSendReplyNoAdminReplyTo:
+    def test_send_reply_has_no_reply_to_header(self, mocker):
+        """Mid-registration conversational emails must not carry a Reply-To header."""
+        channel = EmailChannel(
+            imap_host="imap.example.com",
+            imap_port=993,
+            smtp_host="smtp.example.com",
+            smtp_port=587,
+            username="agent@example.com",
+            password="secret",
+            use_ssl=True,
+            use_tls=True,
+            registration_email="agent@example.com",
+        )
+
+        mock_smtp_cls = mocker.patch("smtplib.SMTP")
+        captured = {}
+
+        def fake_sendmail(from_, to_, msg_str):
+            captured["msg"] = msg_str
+
+        mock_smtp_cls.return_value.sendmail.side_effect = fake_sendmail
+
+        channel.send_reply(
+            to="parent@example.com",
+            subject="Re: Anmeldung",
+            body="Wie heisst dein Kind?",
+        )
+
+        parsed = email.message_from_string(captured["msg"])
+        assert parsed.get("Reply-To") is None

tests/test_notifier.py

@@ -345,3 +345,143 @@ class TestGenerateQrBillPng:
         """Output starts with the PNG magic bytes."""
         png = notifier._generate_qr_bill_png()
         assert png[:4] == b"\x89PNG"
+
+
+# ---------------------------------------------------------------------------
+# Reply-To header — confirmation email to parent (task 1.3)
+# ---------------------------------------------------------------------------
+
+
+class TestNotifyParentReplyTo:
+    def test_confirmation_email_has_reply_to_admin(
+        self, notifier, complete_registration, mocker
+    ):
+        """Confirmation email sets Reply-To to the first CC (admin) address."""
+        mock_smtp_cls = mocker.patch("smtplib.SMTP")
+        captured = {}
+
+        def fake_sendmail(from_, to_, msg_str):
+            captured["msg"] = msg_str
+
+        mock_smtp_cls.return_value.sendmail.side_effect = fake_sendmail
+
+        notifier.notify_parent(complete_registration, language="de")
+
+        parsed = email.message_from_string(captured["msg"])
+        assert parsed.get("Reply-To") == "markus@example.com"
+
+    def test_confirmation_email_no_reply_to_when_no_cc(
+        self, complete_registration, mocker
+    ):
+        """When no CC emails are configured, no Reply-To header is set."""
+        notifier_no_cc = AdminNotifier(
+            smtp_host="smtp.example.com",
+            smtp_port=587,
+            username="agent@example.com",
+            password="secret",
+            from_email="agent@example.com",
+            cc_emails=[],
+        )
+        mock_smtp_cls = mocker.patch("smtplib.SMTP")
+        captured = {}
+
+        def fake_sendmail(from_, to_, msg_str):
+            captured["msg"] = msg_str
+
+        mock_smtp_cls.return_value.sendmail.side_effect = fake_sendmail
+
+        notifier_no_cc.notify_parent(complete_registration, language="de")
+
+        parsed = email.message_from_string(captured["msg"])
+        assert parsed.get("Reply-To") is None
+
+
+# ---------------------------------------------------------------------------
+# Reply-To header — admin notification emails (tasks 2.3, 2.4, 2.5)
+# ---------------------------------------------------------------------------
+
+
+class TestNotifyAdminReplyTo:
+    def _capture_msg(self, mocker):
+        """Return a side-effect function and a dict that captures the raw MIME string."""
+        captured = {}
+
+        mock_smtp_cls = mocker.patch("smtplib.SMTP")
+
+        def fake_sendmail(from_, to_, msg_str):
+            captured["msg"] = msg_str
+
+        mock_smtp_cls.return_value.sendmail.side_effect = fake_sendmail
+        return captured
+
+    def test_indoor_notification_reply_to_is_parent_email(
+        self, notifier, complete_registration, mocker
+    ):
+        """Indoor-only notification sets Reply-To to the parent's email."""
+        from src.models.registration import Booking, BookingDay
+
+        complete_registration.booking = Booking(
+            playgroup_types=["indoor"],
+            selected_days=[BookingDay(day="monday", type="indoor")],
+        )
+        captured = self._capture_msg(mocker)
+
+        notifier.notify_admin(
+            complete_registration,
+            registration_id="reg-001",
+            version=1,
+            conversation_id="conv-001",
+            channel="email",
+        )
+
+        parsed = email.message_from_string(captured["msg"])
+        assert parsed.get("Reply-To") == "anna.muster@example.com"
+
+    def test_outdoor_notification_reply_to_is_parent_email(
+        self, notifier, complete_registration, mocker
+    ):
+        """Outdoor-only notification sets Reply-To to the parent's email."""
+        from src.models.registration import Booking, BookingDay
+
+        complete_registration.booking = Booking(
+            playgroup_types=["outdoor"],
+            selected_days=[BookingDay(day="monday", type="outdoor")],
+        )
+        captured = self._capture_msg(mocker)
+
+        notifier.notify_admin(
+            complete_registration,
+            registration_id="reg-002",
+            version=1,
+            conversation_id="conv-002",
+            channel="email",
+        )
+
+        parsed = email.message_from_string(captured["msg"])
+        assert parsed.get("Reply-To") == "anna.muster@example.com"
+
+    def test_both_types_notification_reply_to_is_parent_email(
+        self, notifier, complete_registration, mocker
+    ):
+        """Both-types notification sets Reply-To to the parent's email."""
+        from src.models.registration import Booking, BookingDay
+
+        complete_registration.booking = Booking(
+            playgroup_types=["indoor", "outdoor"],
+            selected_days=[
+                BookingDay(day="monday", type="indoor"),
+                BookingDay(day="monday", type="outdoor"),
+            ],
+        )
+        captured = self._capture_msg(mocker)
+
+        notifier.notify_admin(
+            complete_registration,
+            registration_id="reg-003",
+            version=1,
+            conversation_id="conv-003",
+            channel="email",
+        )
+
+        parsed = email.message_from_string(captured["msg"])
+        assert parsed.get("Reply-To") == "anna.muster@example.com"