diff --git a/src/task_processor/models.py b/src/task_processor/models.py
index e7782fe..6d198a5 100644
--- a/src/task_processor/models.py
+++ b/src/task_processor/models.py
@@ -180,7 +180,23 @@ def should_execute(self) -> bool:
             # If we have never run this task, then we should execute it only if
             # the time has passed after which we want to ensure this task runs.
             # This allows us to control when intensive tasks should be run.
-            return not (self.first_run_time and self.first_run_time > now.time())
+            if not self.first_run_time:
+                return True
+            first_run_today = now.replace(
+                hour=self.first_run_time.hour,
+                minute=self.first_run_time.minute,
+                second=self.first_run_time.second,
+                microsecond=self.first_run_time.microsecond,
+            )
+            # Handle midnight boundary using 12-hour window heuristic.
+            time_difference = (now - first_run_today).total_seconds()
+            if time_difference > 12 * 3600:
+                # first_run_today appears far in the past; it refers to tomorrow.
+                return False
+            if time_difference < -12 * 3600:
+                # first_run_today appears far in the future; it refers to yesterday.
+                return True
+            return now >= first_run_today
 
         # if the last run was at t- run_every, then we should execute it
         if (timezone.now() - last_task_run.started_at) >= self.run_every:
diff --git a/tests/unit/task_processor/test_unit_task_processor_models.py b/tests/unit/task_processor/test_unit_task_processor_models.py
index 0adc96b..0fb6a0c 100644
--- a/tests/unit/task_processor/test_unit_task_processor_models.py
+++ b/tests/unit/task_processor/test_unit_task_processor_models.py
@@ -3,6 +3,7 @@
 
 import pytest
 from django.utils import timezone
+from freezegun import freeze_time
 from pytest_mock import MockerFixture
 
 from task_processor.decorators import register_task_handler
@@ -80,3 +81,31 @@ def test_recurring_task_run_should_execute_first_run_at(
         ).should_execute
         == expected
     )
+
+
+@freeze_time("2026-01-15 23:05:23")
+def test_recurring_task_should_execute__first_run_time_after_midnight__returns_false() -> (
+    None
+):
+    # Given
+    task = RecurringTask(
+        first_run_time=time(0, 5, 23),
+        run_every=timedelta(days=1),
+    )
+
+    # When & Then
+    assert task.should_execute is False
+
+
+@freeze_time("2026-01-16 00:30:00")
+def test_recurring_task_should_execute__first_run_time_before_midnight__returns_true() -> (
+    None
+):
+    # Given
+    task = RecurringTask(
+        first_run_time=time(23, 0, 0),
+        run_every=timedelta(days=1),
+    )
+
+    # When & Then
+    assert task.should_execute is True