diff --git a/api/tacticalrmm/winupdate/migrations/0008_auto_20200911_0415.py b/api/tacticalrmm/winupdate/migrations/0008_auto_20200911_0415.py
new file mode 100644
index 00000000..f99b078f
--- /dev/null
+++ b/api/tacticalrmm/winupdate/migrations/0008_auto_20200911_0415.py
@@ -0,0 +1,18 @@
+# Generated by Django 3.1.1 on 2020-09-11 04:15
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('winupdate', '0007_winupdatepolicy_run_time_day'),
+    ]
+
+    operations = [
+        migrations.AlterField(
+            model_name='winupdatepolicy',
+            name='run_time_day',
+            field=models.IntegerField(choices=[(1, 1), (2, 2), (3, 3), (4, 4), (5, 5), (6, 6), (7, 7), (8, 8), (9, 9), (10, 10), (11, 11), (12, 12), (13, 13), (14, 14), (15, 15), (16, 16), (17, 17), (18, 18), (19, 19), (20, 20), (21, 21), (22, 22), (23, 23), (24, 24), (25, 25), (26, 26), (27, 27), (28, 28), (29, 29), (30, 30), (31, 31)], default=1),
+        ),
+    ]
diff --git a/api/tacticalrmm/winupdate/models.py b/api/tacticalrmm/winupdate/models.py
index 4a5841a5..be48fd42 100644
--- a/api/tacticalrmm/winupdate/models.py
+++ b/api/tacticalrmm/winupdate/models.py
@@ -21,7 +21,7 @@ AUTO_APPROVAL_CHOICES = [
 
 RUN_TIME_HOUR_CHOICES = [(i, dt.time(i).strftime("%I %p")) for i in range(24)]
 
-RUN_TIME_DAY_CHOICES = [(i, dt.date(1970, 1, 1).strftime("%-d")) for i in range(31)]
+RUN_TIME_DAY_CHOICES = [(i + 1, i + 1) for i in range(31)]
 
 REBOOT_AFTER_INSTALL_CHOICES = [
     ("never", "Never"),
diff --git a/api/tacticalrmm/winupdate/tasks.py b/api/tacticalrmm/winupdate/tasks.py
index 9b147b97..e7c3e7c2 100644
--- a/api/tacticalrmm/winupdate/tasks.py
+++ b/api/tacticalrmm/winupdate/tasks.py
@@ -60,41 +60,41 @@ def check_agent_update_schedule_task():
             hour = int(agent_localtime_now.strftime("%-H"))
             day = int(agent_localtime_now.strftime("%-d"))
 
-            # get agent last installed time in local time zone
-            last_installed = agent.patches_last_installed.astimezone(timezone)
+            if agent.patches_last_installed:
+                # get agent last installed time in local time zone
+                last_installed = agent.patches_last_installed.astimezone(timezone)
 
-            # check if patches were already run for this cycle and exit if so
-            if last_installed and last_installed.strftime(
-                "%d/%m/%Y"
-            ) == agent_localtime_now.strftime("%d/%m/%Y"):
-                return
+                # check if patches were already run for this cycle and exit if so
+                if last_installed.strftime("%d/%m/%Y") == agent_localtime_now.strftime(
+                    "%d/%m/%Y"
+                ):
+                    return
 
-            # check if schedule is set to daily/weekly
-            if patch_policy.run_time_frequency == "weekly":
-
-                # check if patches were scheduled to run today
-                if weekday in patch_policy.run_time_days:
-
-                    # check if patches are past due
-                    if patch_policy.run_time_hour < hour:
-                        install = True
+            # check if schedule is set to daily/weekly and if now is the time to run
+            if (
+                patch_policy.run_time_frequency == "daily"
+                and weekday in patch_policy.run_time_days
+                and patch_policy.run_time_hour == hour
+            ):
+                install = True
 
             elif patch_policy.run_time_frequency == "monthly":
 
                 if patch_policy.run_time_day > 28:
                     months_with_30_days = [3, 6, 9, 11]
-                    current_month = agent_localtime_now.strftime("%-m")
+                    current_month = int(agent_localtime_now.strftime("%-m"))
 
                     if current_month == 2:
                         patch_policy.run_time_day = 28
                     elif current_month in months_with_30_days:
                         patch_policy.run_time_day = 30
 
-                # check if patches were scheduled to run today
-                if day == patch_policy.run_time_day:
-                    # check if patches are past due
-                    if patch_policy.run_time_hour < hour:
-                        install = True
+                # check if patches were scheduled to run today and now
+                if (
+                    day == patch_policy.run_time_day
+                    and patch_policy.run_time_hour == hour
+                ):
+                    install = True
 
             if install:
                 # initiate update on agent asynchronously and don't worry about ret code