diff --git a/homeassistant/components/automation/__init__.py b/homeassistant/components/automation/__init__.py
index 373a45b4103..a2ee5083ea5 100644
--- a/homeassistant/components/automation/__init__.py
+++ b/homeassistant/components/automation/__init__.py
@@ -14,6 +14,7 @@ import voluptuous as vol
 
 from homeassistant.components import labs, websocket_api
 from homeassistant.components.blueprint import CONF_USE_BLUEPRINT
+from homeassistant.components.labs import async_listen as async_labs_listen
 from homeassistant.const import (
     ATTR_ENTITY_ID,
     ATTR_MODE,
@@ -345,6 +346,20 @@ async def async_setup(hass: HomeAssistant, config: ConfigType) -> bool:
         schema=vol.Schema({vol.Optional(CONF_ID): str}),
     )
 
+    @callback
+    def new_triggers_conditions_listener() -> None:
+        """Handle new_triggers_conditions flag change."""
+        hass.async_create_task(
+            reload_helper.execute_service(ServiceCall(hass, DOMAIN, SERVICE_RELOAD))
+        )
+
+    async_labs_listen(
+        hass,
+        DOMAIN,
+        NEW_TRIGGERS_CONDITIONS_FEATURE_FLAG,
+        new_triggers_conditions_listener,
+    )
+
     websocket_api.async_register_command(hass, websocket_config)
 
     return True
diff --git a/tests/components/automation/test_init.py b/tests/components/automation/test_init.py
index 243e132dae2..0b5f8e109ce 100644
--- a/tests/components/automation/test_init.py
+++ b/tests/components/automation/test_init.py
@@ -8,7 +8,7 @@ from unittest.mock import ANY, Mock, patch
 
 import pytest
 
-from homeassistant.components import automation, input_boolean, script
+from homeassistant.components import automation, input_boolean, labs, script
 from homeassistant.components.automation import (
     ATTR_SOURCE,
     DOMAIN,
@@ -3493,3 +3493,92 @@ async def test_valid_configuration(
         },
     )
     await hass.async_block_till_done()
+
+
+async def test_reload_when_labs_flag_changes(
+    hass: HomeAssistant,
+    hass_ws_client: WebSocketGenerator,
+    calls: list[ServiceCall],
+    hass_admin_user: MockUser,
+    hass_read_only_user: MockUser,
+) -> None:
+    """Test automations are reloaded when labs flag changes."""
+    ws_client = await hass_ws_client(hass)
+
+    assert await async_setup_component(
+        hass,
+        automation.DOMAIN,
+        {
+            automation.DOMAIN: {
+                "alias": "hello",
+                "trigger": {"platform": "event", "event_type": "test_event"},
+                "action": {
+                    "action": "test.automation",
+                    "data_template": {"event": "{{ trigger.event.event_type }}"},
+                },
+            }
+        },
+    )
+    assert await async_setup_component(hass, labs.DOMAIN, {})
+    assert hass.states.get("automation.hello") is not None
+    assert hass.states.get("automation.bye") is None
+    listeners = hass.bus.async_listeners()
+    assert listeners.get("test_event") == 1
+    assert listeners.get("test_event2") is None
+
+    hass.bus.async_fire("test_event")
+    await hass.async_block_till_done()
+
+    assert len(calls) == 1
+    assert calls[0].data.get("event") == "test_event"
+
+    test_reload_event = async_capture_events(hass, EVENT_AUTOMATION_RELOADED)
+
+    # Check we reload whenever the labs flag is set, even if it's already enabled
+    for enabled in (True, True, False, False):
+        test_reload_event.clear()
+        calls.clear()
+
+        with patch(
+            "homeassistant.config.load_yaml_config_file",
+            autospec=True,
+            return_value={
+                automation.DOMAIN: {
+                    "alias": "bye",
+                    "trigger": {"platform": "event", "event_type": "test_event2"},
+                    "action": {
+                        "action": "test.automation",
+                        "data_template": {"event": "{{ trigger.event.event_type }}"},
+                    },
+                }
+            },
+        ):
+            await ws_client.send_json_auto_id(
+                {
+                    "type": "labs/update",
+                    "domain": "automation",
+                    "preview_feature": "new_triggers_conditions",
+                    "enabled": enabled,
+                }
+            )
+
+            msg = await ws_client.receive_json()
+            assert msg["success"]
+            await hass.async_block_till_done()
+
+        assert len(test_reload_event) == 1
+
+        assert hass.states.get("automation.hello") is None
+        assert hass.states.get("automation.bye") is not None
+        listeners = hass.bus.async_listeners()
+        assert listeners.get("test_event") is None
+        assert listeners.get("test_event2") == 1
+
+        hass.bus.async_fire("test_event")
+        await hass.async_block_till_done()
+        assert len(calls) == 0
+
+        hass.bus.async_fire("test_event2")
+        await hass.async_block_till_done()
+        assert len(calls) == 1
+        assert calls[-1].data.get("event") == "test_event2"