fix(log): roll daily log file at midnight for long-running processes

The log filename was computed once at init_logging() startup and the
RotatingFileHandler only rotated by size, so a process running across
midnight kept appending every subsequent day's logs to the start-day
file (langbot-<start date>.log). No file ever appeared for the current
day until the process was restarted, confusing users into thinking
logging had stopped.

Replace RotatingFileHandler with DailyGroupedRotatingFileHandler, which
switches to langbot-<current date>.log when the local date changes while
still doing size-based numbered rotation within a day. On-disk naming
stays compatible with the maintenance log-retention cleanup
(LOG_FILE_PATTERN). Adds regression tests.

src/langbot/pkg/core/bootutils/log.py

@@ -1,5 +1,6 @@
 import logging
 import logging.handlers
+import os
 import sys
 import time
 
@@ -20,6 +21,66 @@ log_colors_config = {
 LOG_FILE_MAX_BYTES = 10 * 1024 * 1024  # 10MB per file
 LOG_FILE_BACKUP_COUNT = 5  # Keep 5 backup files (total ~50MB max)
 
+LOG_DIR = 'data/logs'
+
+
+class DailyGroupedRotatingFileHandler(logging.handlers.RotatingFileHandler):
+    """File handler that writes to ``data/logs/langbot-YYYY-MM-DD.log``.
+
+    It combines two rotation triggers:
+
+    * **Size** — within a single day the file is rotated once it exceeds
+      ``maxBytes``, producing numbered backups (``langbot-DATE.log.1`` etc.),
+      exactly like :class:`~logging.handlers.RotatingFileHandler`.
+    * **Date** — when the local date changes, logging switches to a fresh
+      ``langbot-<new date>.log`` file. This happens even within a single
+      long-running process, so a bot started on day N keeps writing to that
+      day's file and rolls over to day N+1's file at midnight, instead of
+      appending every subsequent day's logs to the start-day file.
+
+    The on-disk naming stays compatible with the log-retention cleanup in
+    ``api/http/service/maintenance.py`` (``LOG_FILE_PATTERN``).
+    """
+
+    def __init__(self, log_dir: str, max_bytes: int, backup_count: int, encoding: str = 'utf-8'):
+        self.log_dir = log_dir
+        self._current_date = self._today()
+        super().__init__(
+            self._build_path(self._current_date),
+            maxBytes=max_bytes,
+            backupCount=backup_count,
+            encoding=encoding,
+        )
+
+    @staticmethod
+    def _today() -> str:
+        return time.strftime('%Y-%m-%d', time.localtime())
+
+    def _build_path(self, date_str: str) -> str:
+        return os.path.join(self.log_dir, 'langbot-%s.log' % date_str)
+
+    def shouldRollover(self, record):
+        # Roll over when the day changes, regardless of file size.
+        if self._today() != self._current_date:
+            return True
+        return super().shouldRollover(record)
+
+    def doRollover(self):
+        today = self._today()
+        if today != self._current_date:
+            # Date changed: point the handler at the new day's file.
+            # This is a date switch, not a size-based numbered rotation.
+            if self.stream:
+                self.stream.close()
+                self.stream = None
+            self._current_date = today
+            self.baseFilename = os.path.abspath(self._build_path(today))
+            if not self.delay:
+                self.stream = self._open()
+        else:
+            # Same day, file exceeded maxBytes: numbered rotation.
+            super().doRollover()
+
 
 async def init_logging(extra_handlers: list[logging.Handler] = None) -> logging.Logger:
     # Remove all existing loggers
@@ -31,8 +92,6 @@ async def init_logging(extra_handlers: list[logging.Handler] = None) -> logging.
     if constants.debug_mode:
         level = logging.DEBUG
 
-    log_file_name = 'data/logs/langbot-%s.log' % time.strftime('%Y-%m-%d', time.localtime())
-
     qcg_logger = logging.getLogger('langbot')
 
     qcg_logger.setLevel(level)
@@ -48,12 +107,13 @@ async def init_logging(extra_handlers: list[logging.Handler] = None) -> logging.
     # stream_handler.setFormatter(color_formatter)
     stream_handler.stream = open(sys.stdout.fileno(), mode='w', encoding='utf-8', buffering=1)
 
-    # Use RotatingFileHandler to prevent unbounded log file growth
+    # Rotate by size within a day and switch files when the date changes,
-    rotating_file_handler = logging.handlers.RotatingFileHandler(
+    # so long-running processes still produce a log file for the current day.
-        log_file_name,
+    rotating_file_handler = DailyGroupedRotatingFileHandler(
+        LOG_DIR,
+        max_bytes=LOG_FILE_MAX_BYTES,
+        backup_count=LOG_FILE_BACKUP_COUNT,
         encoding='utf-8',
-        maxBytes=LOG_FILE_MAX_BYTES,
-        backupCount=LOG_FILE_BACKUP_COUNT,
     )
 
     log_handlers: list[logging.Handler] = [

tests/unit_tests/core/test_bootutils_log.py

@@ -0,0 +1,120 @@
+"""Tests for the daily-grouped rotating log file handler.
+
+Regression coverage for the bug where a long-running process names its log
+file after the *start* day and keeps appending to it across midnight, so no
+file ever appears for the current day. See
+``langbot.pkg.core.bootutils.log.DailyGroupedRotatingFileHandler``.
+"""
+
+from __future__ import annotations
+
+import logging
+import os
+import re
+
+import langbot.pkg.core.bootutils.log as logmod
+from langbot.pkg.core.bootutils.log import DailyGroupedRotatingFileHandler
+
+# Mirror of the cleanup pattern in api/http/service/maintenance.py.
+MAINTENANCE_LOG_FILE_PATTERN = re.compile(r'^langbot-(\d{4}-\d{2}-\d{2})\.log(?:\.\d+)?$')
+
+
+def _listing(directory):
+    return sorted(os.listdir(directory))
+
+
+def _make_logger(handler, name):
+    logger = logging.getLogger(name)
+    logger.setLevel(logging.INFO)
+    logger.handlers.clear()
+    logger.addHandler(handler)
+    logger.propagate = False
+    return logger
+
+
+class TestDailyGroupedRotatingFileHandler:
+    def _patch_date(self, monkeypatch, box):
+        """Make the handler read its current date from ``box['date']``."""
+
+        def fake_strftime(fmt, t=None):
+            if fmt == '%Y-%m-%d':
+                return box['date']
+            return '00:00:00'
+
+        monkeypatch.setattr(logmod.time, 'strftime', fake_strftime)
+
+    def test_initial_file_named_for_current_day(self, tmp_path, monkeypatch):
+        box = {'date': '2026-06-08'}
+        self._patch_date(monkeypatch, box)
+
+        handler = DailyGroupedRotatingFileHandler(str(tmp_path), max_bytes=10_000, backup_count=3)
+        logger = _make_logger(handler, 'lb_logtest_initial')
+        logger.info('hello')
+        handler.close()
+
+        assert _listing(tmp_path) == ['langbot-2026-06-08.log']
+
+    def test_same_day_size_rotation_creates_numbered_backups(self, tmp_path, monkeypatch):
+        box = {'date': '2026-06-08'}
+        self._patch_date(monkeypatch, box)
+
+        handler = DailyGroupedRotatingFileHandler(str(tmp_path), max_bytes=200, backup_count=3)
+        logger = _make_logger(handler, 'lb_logtest_size')
+        for i in range(40):
+            logger.info('padding line to exceed maxBytes %d', i)
+        handler.close()
+
+        files = _listing(tmp_path)
+        assert 'langbot-2026-06-08.log' in files
+        assert any(f.startswith('langbot-2026-06-08.log.') for f in files)
+
+    def test_rolls_to_new_file_when_day_changes(self, tmp_path, monkeypatch):
+        box = {'date': '2026-06-08'}
+        self._patch_date(monkeypatch, box)
+
+        handler = DailyGroupedRotatingFileHandler(str(tmp_path), max_bytes=10_000, backup_count=3)
+        logger = _make_logger(handler, 'lb_logtest_midnight')
+        logger.info('day1 line')
+
+        # Simulate crossing midnight within the same running process.
+        box['date'] = '2026-06-09'
+        logger.info('day2 line after midnight')
+        handler.close()
+
+        files = _listing(tmp_path)
+        assert 'langbot-2026-06-08.log' in files
+        assert 'langbot-2026-06-09.log' in files
+
+        day2 = (tmp_path / 'langbot-2026-06-09.log').read_text(encoding='utf-8')
+        assert 'day2 line after midnight' in day2
+        assert 'day1 line' not in day2
+
+    def test_rollover_repeats_across_multiple_days(self, tmp_path, monkeypatch):
+        box = {'date': '2026-06-08'}
+        self._patch_date(monkeypatch, box)
+
+        handler = DailyGroupedRotatingFileHandler(str(tmp_path), max_bytes=10_000, backup_count=3)
+        logger = _make_logger(handler, 'lb_logtest_multiday')
+        for day in ('2026-06-08', '2026-06-09', '2026-06-10'):
+            box['date'] = day
+            logger.info('line for %s', day)
+        handler.close()
+
+        files = _listing(tmp_path)
+        for day in ('2026-06-08', '2026-06-09', '2026-06-10'):
+            assert f'langbot-{day}.log' in files
+
+    def test_all_filenames_match_maintenance_cleanup_pattern(self, tmp_path, monkeypatch):
+        box = {'date': '2026-06-08'}
+        self._patch_date(monkeypatch, box)
+
+        handler = DailyGroupedRotatingFileHandler(str(tmp_path), max_bytes=200, backup_count=3)
+        logger = _make_logger(handler, 'lb_logtest_pattern')
+        for i in range(40):
+            logger.info('padding line %d', i)
+        box['date'] = '2026-06-09'
+        logger.info('next day line')
+        handler.close()
+
+        for name in _listing(tmp_path):
+            assert MAINTENANCE_LOG_FILE_PATTERN.match(name), name