refactor(datetime): introduce UtcDateTime, remove naive-strip workarounds

Adds a UtcDateTime TypeDecorator (models.py) that enforces aware-UTC on
write and stamps tzinfo=UTC on read. Replaces 26 DateTime column
declarations. Removes 5 production sites that defensively stripped tzinfo
to match SQLite's lossy round-trip. auth.py now coerces legacy session
cookies upward (stamp UTC on parsed naive marker) instead of stripping
live aware markers downward.

The change is Python-side only: UtcDateTime.impl = DateTime, so DDL and
emitted SQL are unchanged. No Alembic migration needed.

Adds 2 unit tests in test_models.py pinning the decorator's contract
independently of the column declarations.

The three deliberately-naive test_timeago.py fixtures (lines 67, 73, 113)
remain naive on purpose -- they exercise _ensure_utc's normalize-up path
at the public filter boundary, which stays as belt-and-braces defense.

See docs/superpowers/specs/2026-05-16-tz-aware-datetime-design.md.

Co-Authored-By: Claude Opus 4.7 (1M context) <noreply@anthropic.com>

l4d2web/l4d2web/auth.py

@@ -1,4 +1,4 @@
-from datetime import datetime
+from datetime import UTC, datetime
 from functools import wraps
 from typing import Callable, TypeVar
 from urllib.parse import quote, unquote
@@ -53,11 +53,12 @@ def load_current_user() -> None:
     except ValueError:
         g.user = None
         return
-    # user.password_changed_at comes back naive from SQLite; strip tz from the
-    # marker so an aware-marker session (just stamped from an in-memory user)
-    # compares cleanly with a freshly-loaded user row.
-    if marker_dt.tzinfo is not None:
-        marker_dt = marker_dt.replace(tzinfo=None)
+    # Legacy sessions minted before the UtcDateTime migration carry naive
+    # ISO markers; stamp UTC so the comparison against the now-aware DB
+    # value works. Cheap permanent defense; no reliable signal for "all
+    # naive cookies have expired."
+    if marker_dt.tzinfo is None:
+        marker_dt = marker_dt.replace(tzinfo=UTC)
     if marker_dt < user.password_changed_at:
         g.user = None
         return

l4d2web/l4d2web/models.py

@@ -9,6 +9,7 @@ from sqlalchemy import (
     Integer,
     String,
     Text,
+    TypeDecorator,
     UniqueConstraint,
     text,
 )
@@ -23,6 +24,34 @@ def now_utc() -> datetime:
     return datetime.now(UTC)
 
 
+class UtcDateTime(TypeDecorator):
+    """Always store and surface UTC-aware datetimes.
+
+    SQLite has no native tz-aware type and pysqlite strips tzinfo on
+    round-trip. We convert inputs to UTC, persist them as naive UTC under
+    the hood, and re-stamp tzinfo=UTC on read. The result: every datetime
+    on a model attribute is aware UTC, always.
+    """
+
+    impl = DateTime
+    cache_ok = True
+
+    def process_bind_param(self, value, dialect):
+        if value is None:
+            return None
+        if value.tzinfo is None:
+            raise TypeError(
+                "naive datetime passed to UtcDateTime column; "
+                "all writes must be UTC-aware"
+            )
+        return value.astimezone(UTC).replace(tzinfo=None)
+
+    def process_result_value(self, value, dialect):
+        if value is None:
+            return None
+        return value.replace(tzinfo=UTC)
+
+
 class User(Base):
     __tablename__ = "users"
 
@@ -33,9 +62,9 @@ class User(Base):
     active: Mapped[bool] = mapped_column(
         Boolean, default=True, nullable=False, server_default=text("1"),
     )
-    created_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
-    updated_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
-    password_changed_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
+    created_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
+    updated_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
+    password_changed_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
 
 
 class Overlay(Base):
@@ -65,8 +94,8 @@ class Overlay(Base):
     user_id: Mapped[int | None] = mapped_column(ForeignKey("users.id"), nullable=True)
     script: Mapped[str] = mapped_column(Text, default="", nullable=False)
     last_build_status: Mapped[str] = mapped_column(String(16), default="", nullable=False)
-    created_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
-    updated_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
+    created_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
+    updated_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
 
 
 class WorkshopItem(Base):
@@ -80,10 +109,10 @@ class WorkshopItem(Base):
     file_size: Mapped[int] = mapped_column(BigInteger, default=0, nullable=False)
     time_updated: Mapped[int] = mapped_column(Integer, default=0, nullable=False)
     preview_url: Mapped[str] = mapped_column(Text, default="", nullable=False)
-    last_downloaded_at: Mapped[datetime | None] = mapped_column(DateTime, nullable=True)
+    last_downloaded_at: Mapped[datetime | None] = mapped_column(UtcDateTime, nullable=True)
     last_error: Mapped[str] = mapped_column(Text, default="", nullable=False)
-    created_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
-    updated_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
+    created_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
+    updated_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
 
 
 class OverlayWorkshopItem(Base):
@@ -110,8 +139,8 @@ class Blueprint(Base):
     name: Mapped[str] = mapped_column(String(128), nullable=False)
     arguments: Mapped[str] = mapped_column(Text, default="[]", nullable=False)
     config: Mapped[str] = mapped_column(Text, default="[]", nullable=False)
-    created_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
-    updated_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
+    created_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
+    updated_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
 
 
 class BlueprintOverlay(Base):
@@ -124,8 +153,8 @@ class BlueprintOverlay(Base):
     expose_server_cfg: Mapped[bool] = mapped_column(
         Boolean, nullable=False, default=False, server_default=text("0")
     )
-    created_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
-    updated_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
+    created_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
+    updated_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
 
 
 class Server(Base):
@@ -141,7 +170,7 @@ class Server(Base):
     port: Mapped[int] = mapped_column(Integer, unique=True, nullable=False)
     desired_state: Mapped[str] = mapped_column(String(16), default="stopped", nullable=False)
     actual_state: Mapped[str] = mapped_column(String(16), default="unknown", nullable=False)
-    actual_state_updated_at: Mapped[datetime | None] = mapped_column(DateTime, nullable=True)
+    actual_state_updated_at: Mapped[datetime | None] = mapped_column(UtcDateTime, nullable=True)
     last_error: Mapped[str] = mapped_column(Text, default="", nullable=False)
     rcon_password: Mapped[str] = mapped_column(
         String(64), nullable=False, default="", server_default=""
@@ -149,8 +178,8 @@ class Server(Base):
     hostname: Mapped[str] = mapped_column(
         String(128), nullable=False, default="", server_default=""
     )
-    created_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
-    updated_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
+    created_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
+    updated_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
 
 
 class Job(Base):
@@ -163,10 +192,10 @@ class Job(Base):
     operation: Mapped[str] = mapped_column(String(32), nullable=False)
     state: Mapped[str] = mapped_column(String(16), default="queued", nullable=False)
     exit_code: Mapped[int | None] = mapped_column(Integer, nullable=True)
-    started_at: Mapped[datetime | None] = mapped_column(DateTime, nullable=True)
-    finished_at: Mapped[datetime | None] = mapped_column(DateTime, nullable=True)
-    created_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
-    updated_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
+    started_at: Mapped[datetime | None] = mapped_column(UtcDateTime, nullable=True)
+    finished_at: Mapped[datetime | None] = mapped_column(UtcDateTime, nullable=True)
+    created_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
+    updated_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
 
 
 class JobLog(Base):
@@ -177,7 +206,7 @@ class JobLog(Base):
     seq: Mapped[int] = mapped_column(Integer, nullable=False)
     stream: Mapped[str] = mapped_column(String(8), nullable=False)
     line: Mapped[str] = mapped_column(Text, nullable=False)
-    created_at: Mapped[datetime] = mapped_column(DateTime, default=now_utc, nullable=False)
+    created_at: Mapped[datetime] = mapped_column(UtcDateTime, default=now_utc, nullable=False)
 
 
 class ServerLiveState(Base):
@@ -191,8 +220,8 @@ class ServerLiveState(Base):
     server_id: Mapped[int] = mapped_column(
         ForeignKey("servers.id", ondelete="CASCADE"), nullable=False
     )
-    started_at: Mapped[datetime] = mapped_column(DateTime, nullable=False)
-    last_seen_at: Mapped[datetime] = mapped_column(DateTime, nullable=False)
+    started_at: Mapped[datetime] = mapped_column(UtcDateTime, nullable=False)
+    last_seen_at: Mapped[datetime] = mapped_column(UtcDateTime, nullable=False)
     players: Mapped[int] = mapped_column(Integer, nullable=False)
     max_players: Mapped[int] = mapped_column(Integer, nullable=False)
     bots: Mapped[int] = mapped_column(Integer, nullable=False)
@@ -213,8 +242,8 @@ class ServerPlayerSession(Base):
         ForeignKey("servers.id", ondelete="CASCADE"), nullable=False
     )
     steam_id_64: Mapped[str] = mapped_column(String(20), nullable=False)
-    joined_at: Mapped[datetime] = mapped_column(DateTime, nullable=False)
-    left_at: Mapped[datetime | None] = mapped_column(DateTime, nullable=True)
+    joined_at: Mapped[datetime] = mapped_column(UtcDateTime, nullable=False)
+    left_at: Mapped[datetime | None] = mapped_column(UtcDateTime, nullable=True)
     name_at_join: Mapped[str] = mapped_column(String(64), nullable=False)
     min_ping: Mapped[int] = mapped_column(Integer, nullable=False)
     max_ping: Mapped[int] = mapped_column(Integer, nullable=False)
@@ -226,7 +255,7 @@ class SteamUserProfile(Base):
     steam_id_64: Mapped[str] = mapped_column(String(20), primary_key=True)
     persona_name: Mapped[str] = mapped_column(String(64), nullable=False)
     avatar_url: Mapped[str] = mapped_column(Text, nullable=False)
-    fetched_at: Mapped[datetime] = mapped_column(DateTime, nullable=False)
+    fetched_at: Mapped[datetime] = mapped_column(UtcDateTime, nullable=False)
 
 
 class CommandHistory(Base):
@@ -248,5 +277,5 @@ class CommandHistory(Base):
         Boolean, nullable=False, default=False, server_default=text("0")
     )
     created_at: Mapped[datetime] = mapped_column(
-        DateTime, default=now_utc, nullable=False
+        UtcDateTime, default=now_utc, nullable=False
     )

l4d2web/l4d2web/routes/page_routes.py

@@ -171,7 +171,7 @@ def servers_page() -> str:
         ).all()
 
         stale_seconds = current_app.config.get("LIVE_STATE_STALE_SECONDS", 30)
-        cutoff = datetime.now(UTC).replace(tzinfo=None) - timedelta(seconds=stale_seconds)
+        cutoff = datetime.now(UTC) - timedelta(seconds=stale_seconds)
 
         server_ids = [s.id for s, _bp in rows]
         latest_rows: dict[int, ServerLiveState] = {}

l4d2web/l4d2web/routes/profile_routes.py

@@ -83,9 +83,7 @@ def profile_password_change() -> Response:
         if user is None or not verify_password(current_password, user.password_digest):
             return _redirect_with_error("wrong_current")
         user.password_digest = hash_password(new_password)
-        # Strip tz so the marker matches what a subsequent DB read returns
-        # (SQLite DateTime columns don't preserve tzinfo).
-        user.password_changed_at = now_utc().replace(tzinfo=None)
+        user.password_changed_at = now_utc()
         new_marker = user.password_changed_at.isoformat()
 
     session["pw_changed_at"] = new_marker

l4d2web/l4d2web/routes/server_routes.py

@@ -207,7 +207,7 @@ def live_state_fragment(server_id: int) -> Response:
             return Response(status=404)
 
         stale_seconds = current_app.config.get("LIVE_STATE_STALE_SECONDS", 30)
-        cutoff = datetime.now(UTC).replace(tzinfo=None) - timedelta(seconds=stale_seconds)
+        cutoff = datetime.now(UTC) - timedelta(seconds=stale_seconds)
 
         latest = db.scalar(
             select(ServerLiveState)
@@ -231,7 +231,7 @@ def live_state_fragment(server_id: int) -> Response:
 
         current_ids = [r[0].steam_id_64 for r in current_rows]
 
-        recent_cutoff = datetime.now(UTC).replace(tzinfo=None) - timedelta(
+        recent_cutoff = datetime.now(UTC) - timedelta(
             days=current_app.config.get("LIVE_STATE_HISTORY_DAYS", 30)
         )
 

l4d2web/l4d2web/services/live_state_poller.py

@@ -34,7 +34,7 @@ logger = logging.getLogger(__name__)
 
 
 def _now() -> datetime:
-    return datetime.now(UTC).replace(tzinfo=None)
+    return datetime.now(UTC)
 
 
 def poll_once() -> None:

l4d2web/tests/test_models.py

@@ -1,3 +1,6 @@
+from datetime import UTC, datetime
+
+import pytest
 from sqlalchemy import select
 
 from l4d2web.db import init_db, session_scope
@@ -8,6 +11,7 @@ from l4d2web.models import (
     ServerPlayerSession,
     SteamUserProfile,
     User,
+    UtcDateTime,
     now_utc as now_utc_aware,
 )
 
@@ -108,3 +112,15 @@ def test_steam_user_profile_table_columns(tmp_path, monkeypatch) -> None:
             fetched_at=now_utc_aware(),
         )
         db.add(row); db.flush()
+
+
+def test_utc_datetime_rejects_naive_bind() -> None:
+    with pytest.raises(TypeError, match="naive"):
+        UtcDateTime().process_bind_param(datetime(2026, 5, 16, 12, 0), None)
+
+
+def test_utc_datetime_stamps_utc_on_read() -> None:
+    naive = datetime(2026, 5, 16, 12, 0)
+    result = UtcDateTime().process_result_value(naive, None)
+    assert result == datetime(2026, 5, 16, 12, 0, tzinfo=UTC)
+    assert result.tzinfo == UTC