diff --git a/api/tacticalrmm/autotasks/tasks.py b/api/tacticalrmm/autotasks/tasks.py
index d5583786..a2a33822 100644
--- a/api/tacticalrmm/autotasks/tasks.py
+++ b/api/tacticalrmm/autotasks/tasks.py
@@ -1,7 +1,8 @@
 from loguru import logger
 from tacticalrmm.celery import app
 from django.conf import settings
-from datetime import datetime as dt
+import pytz
+from django.utils import timezone as djangotime
 
 from .models import AutomatedTask
 from logs.models import PendingAction
@@ -46,6 +47,16 @@ def create_win_task_schedule(pk, pending_action=False):
 
     elif task.task_type == "runonce":
 
+        # check if scheduled time is in the past
+        agent_tz = pytz.timezone(task.agent.timezone)
+        task_time_utc = task.run_time_date.replace(tzinfo=agent_tz).astimezone(pytz.utc)
+        now = djangotime.now()
+        if task_time_utc < now:
+            task.run_time_date = now.astimezone(agent_tz).replace(
+                tzinfo=pytz.utc
+            ) + djangotime.timedelta(minutes=5)
+            task.save()
+
         r = task.agent.salt_api_cmd(
             timeout=20,
             func="task.create_task",
@@ -61,6 +72,7 @@ def create_win_task_schedule(pk, pending_action=False):
                 f'start_time="{task.run_time_date.strftime("%H:%M")}"',
                 "ac_only=False",
                 "stop_if_on_batteries=False",
+                "start_when_available=True",
             ],
         )
 
diff --git a/api/tacticalrmm/core/tasks.py b/api/tacticalrmm/core/tasks.py
index b8f2a4cf..54f03e16 100644
--- a/api/tacticalrmm/core/tasks.py
+++ b/api/tacticalrmm/core/tasks.py
@@ -25,8 +25,9 @@ def core_maintenance_tasks():
 
     # cleanup expired runonce tasks
     tasks = AutomatedTask.objects.filter(
-        task_type="runonce", remove_if_not_scheduled=True
-    )
+        task_type="runonce",
+        remove_if_not_scheduled=True,
+    ).exclude(last_run=None)
 
     for task in tasks:
         agent_tz = pytz.timezone(task.agent.timezone)