diff --git a/files/__main__.py b/files/__main__.py
index f0e1a3be2..8f22f00c4 100644
--- a/files/__main__.py
+++ b/files/__main__.py
@@ -194,11 +194,12 @@ limiter = flask_limiter.Limiter(
 # ...and then after that we can load the database.
 
 engine: Engine = create_engine(DATABASE_URL)
-db_session: scoped_session = scoped_session(sessionmaker(
+db_session_factory: sessionmaker = sessionmaker(
 	bind=engine,
 	autoflush=False,
 	future=True,
-))
+)
+db_session: scoped_session = scoped_session(db_session_factory)
 
 # now that we've that, let's add the cache, compression, and mail extensions to our app...
 
diff --git a/files/commands/cron.py b/files/commands/cron.py
index 1595e98df..4f672f332 100644
--- a/files/commands/cron.py
+++ b/files/commands/cron.py
@@ -4,9 +4,9 @@ import time
 from datetime import datetime, timezone
 from typing import Final
 
-from sqlalchemy.orm import scoped_session, Session
+from sqlalchemy.orm import sessionmaker, Session
 
-from files.__main__ import app, db_session
+from files.__main__ import app, db_session_factory
 from files.classes.cron.tasks import (DayOfWeek, RepeatableTask,
                                       RepeatableTaskRun, ScheduledTaskState)
 
@@ -41,7 +41,7 @@ def cron_app_worker():
 	logging.info("Starting scheduler worker process")
 	while True:
 		try:
-			_run_tasks(db_session)
+			_run_tasks(db_session_factory)
 		except Exception as e:
 			logging.exception(
 				"An unhandled exception occurred while running tasks",
@@ -77,7 +77,7 @@ def _acquire_lock_exclusive(db: Session, table: str):
 		raise
 
 
-def _run_tasks(db_session_factory: scoped_session):
+def _run_tasks(db_session_factory: sessionmaker):
 	'''
 	Runs tasks, attempting to guarantee that a task is ran once and only once.
 	This uses postgres to lock the table containing our tasks at key points in
@@ -87,54 +87,53 @@ def _run_tasks(db_session_factory: scoped_session):
 	running task does not lock the entire table for its entire run, which would
 	for example, prevent any statistics about status from being gathered.
 	'''
+	db: Session = db_session_factory()
 
-	db: Session
-	with db_session_factory() as db:
+	with _acquire_lock_exclusive(db, RepeatableTask.__tablename__):
+		now: datetime = datetime.now(tz=timezone.utc)
+
+		tasks: list[RepeatableTask] = db.query(RepeatableTask).filter(
+			RepeatableTask.enabled == True,
+			RepeatableTask.frequency_day != int(DayOfWeek.NONE),
+			RepeatableTask.run_state != int(ScheduledTaskState.RUNNING),
+			(RepeatableTask.run_time_last <= now)
+				| (RepeatableTask.run_time_last == None),
+		).all()
+
+		# SQLA needs to query again for the inherited object info anyway
+		# so it's fine that objects in the list get expired on txn end.
+		# Prefer more queries to risk of task run duplication.
+		tasks_to_run: list[RepeatableTask] = list(filter(
+			lambda task: task.can_run(now),	tasks))
+
+	for task in tasks_to_run:
+		now = datetime.now(tz=timezone.utc)
 		with _acquire_lock_exclusive(db, RepeatableTask.__tablename__):
-			now: datetime = datetime.now(tz=timezone.utc)
+			# We need to check for runnability again because we don't mutex
+			# the RepeatableTask.run_state until now.
+			if not task.can_run(now):
+				continue
+			task.run_time_last = now
+			task.run_state_enum = ScheduledTaskState.RUNNING
 
-			tasks: list[RepeatableTask] = db.query(RepeatableTask).filter(
-				RepeatableTask.enabled == True,
-				RepeatableTask.frequency_day != int(DayOfWeek.NONE),
-				RepeatableTask.run_state != int(ScheduledTaskState.RUNNING),
-				(RepeatableTask.run_time_last <= now)
-					| (RepeatableTask.run_time_last == None),
-			).all()
+		# This *must* happen before we start doing db queries, including sqlalchemy db queries
+		db.begin()
+		task_debug_identifier = f"(ID {task.id}:{task.label})"
+		logging.info(f"Running task {task_debug_identifier}")
 
-			# SQLA needs to query again for the inherited object info anyway
-			# so it's fine that objects in the list get expired on txn end.
-			# Prefer more queries to risk of task run duplication.
-			tasks_to_run: list[RepeatableTask] = list(filter(
-				lambda task: task.can_run(now),	tasks))
+		run: RepeatableTaskRun = task.run(db, task.run_time_last_or_created_utc)
 
-		for task in tasks_to_run:
-			now = datetime.now(tz=timezone.utc)
-			with _acquire_lock_exclusive(db, RepeatableTask.__tablename__):
-				# We need to check for runnability again because we don't mutex
-				# the RepeatableTask.run_state until now.
-				if not task.can_run(now):
-					continue
-				task.run_time_last = now
-				task.run_state_enum = ScheduledTaskState.RUNNING
+		if run.exception:
+			# TODO: collect errors somewhere other than just here and in the 
+			# task run object itself (see #220).
+			logging.exception(
+				f"Exception running task {task_debug_identifier}", 
+				exc_info=run.exception
+			)
+			db.rollback()
+		else:
+			db.commit()
+			logging.info(f"Finished task {task_debug_identifier}")
 
-			# This *must* happen before we start doing db queries, including sqlalchemy db queries
-			db.begin()
-			task_debug_identifier = f"(ID {task.id}:{task.label})"
-			logging.info(f"Running task {task_debug_identifier}")
-			
-			run: RepeatableTaskRun = task.run(db, task.run_time_last_or_created_utc)
-
-			if run.exception:
-				# TODO: collect errors somewhere other than just here and in the 
-				# task run object itself (see #220).
-				logging.exception(
-					f"Exception running task {task_debug_identifier}", 
-					exc_info=run.exception
-				)
-				db.rollback()
-			else:
-				db.commit()
-				logging.info(f"Finished task {task_debug_identifier}")
-
-			with _acquire_lock_exclusive(db, RepeatableTask.__tablename__):
-				task.run_state_enum = ScheduledTaskState.WAITING
+		with _acquire_lock_exclusive(db, RepeatableTask.__tablename__):
+			task.run_state_enum = ScheduledTaskState.WAITING