Log every DM-email decision point (diagnostic follow-up to #66/#68)

A live "no emails arriving" report produced literally nothing in the
logs, not even the SMTP-not-configured line -- this app has no logging
config lowering the root level below Python's own WARNING default, so
every .debug()/.info() call has been silently invisible in production
all along. Bumped the SMTP-not-configured line to .warning, and added
one at each early-return in _maybe_email_dm_notification (no other
participant, recipient online, already has unread messages) plus a
confirmation right before actually sending -- next attempt will show
exactly which branch is being hit instead of nothing at all.

Co-Authored-By: Claude Sonnet 5 <noreply@anthropic.com>

backend/app/services/email_service.py

@@ -221,7 +221,12 @@ async def send_email(
     """
     cfg = await get_smtp_settings(db)
     if cfg is None:
-        logger.debug("SMTP not configured; skipping email to %s", to_address)
+        # WARNING, not .debug -- this app has no logging config lowering
+        # the root level below Python's own WARNING default, so anything
+        # below that is silently invisible in production (confirmed live:
+        # a real "no emails arriving" report produced nothing in the logs
+        # at all, this line included, even though it was relevant).
+        logger.warning("SMTP not configured; skipping email to %s", to_address)
         return
     palette = await _resolve_palette(db, theme_user)
     html_body = _render_html(palette, subject, paragraphs, cta_label, cta_url)

backend/app/services/message_events.py

@@ -1,4 +1,5 @@
 import asyncio
+import logging
 import uuid
 
 from sqlalchemy import select, update
@@ -16,6 +17,8 @@ from app.ws.focus_presence import FocusPresence
 from app.ws.global_presence import GlobalPresence
 from app.ws.presence import Presence
 
+logger = logging.getLogger(__name__)
+
 
 async def _notify_offline_members(
     db: AsyncSession,
@@ -168,6 +171,17 @@ async def _maybe_email_dm_notification(
     rooms.py's private _member_status (not importable from here), just
     re-derived.
     """
+    # #68 follow-up: this whole function used to have zero logging on any
+    # of its early-return paths, which made "why didn't an email go out"
+    # completely undiagnosable from the outside -- confirmed live, a real
+    # report of "no emails" produced nothing in the logs at all, not even
+    # at the level that turned out to be the actual cause. logger.warning
+    # (not .info/.debug) is deliberate: this app has no logging config
+    # setting the root level below Python's own WARNING default, so
+    # anything logged lower than that is silently invisible in production
+    # regardless of what it's actually about -- these aren't really
+    # warnings, they're the only level guaranteed to reach journalctl
+    # today.
     room = await db.get(Room, room_id)
     if room is None or not room.is_dm:
         return
@@ -179,14 +193,21 @@ async def _maybe_email_dm_notification(
     )
     membership = result.scalar_one_or_none()
     if membership is None:
+        logger.warning("DM email skipped for room %s: no other participant found", room_id)
         return
     recipient = await db.get(User, membership.user_id)
     if recipient is None:
+        logger.warning(
+            "DM email skipped for room %s: recipient user %s not found", room_id, membership.user_id
+        )
         return
     # appear_offline is a manual "always look offline" override -- treated
     # the same as genuinely offline here, same as everywhere else it's
     # checked in this codebase.
     if not recipient.appear_offline and await global_presence.is_online(recipient.id):
+        logger.warning(
+            "DM email skipped for room %s: recipient %s is online", room_id, recipient.id
+        )
         return
 
     # Debounced to the first unread message in this conversation, not
@@ -202,6 +223,11 @@ async def _maybe_email_dm_notification(
         .limit(1)
     )
     if already_unread.scalar_one_or_none() is not None:
+        logger.warning(
+            "DM email skipped for room %s: recipient %s already has unread messages",
+            room_id,
+            recipient.id,
+        )
         return
 
     if message.content:
@@ -211,6 +237,7 @@ async def _maybe_email_dm_notification(
     else:
         body_line = f"{sender.username} sent an image"
     link = f"{base_url.rstrip('/')}/rooms/{room_id}"
+    logger.warning("Sending DM email to %s for room %s", recipient.email, room_id)
     await send_email(
         db,
         recipient.email,