diff --git a/homeassistant/components/template/trigger.py b/homeassistant/components/template/trigger.py
index 80ad585486b..9e6ee086c73 100644
--- a/homeassistant/components/template/trigger.py
+++ b/homeassistant/components/template/trigger.py
@@ -37,21 +37,49 @@ async def async_attach_trigger(
     template.attach(hass, time_delta)
     delay_cancel = None
     job = HassJob(action)
+    armed = False
+
+    # Arm at setup if the template is already false.
+    try:
+        if not result_as_boolean(value_template.async_render()):
+            armed = True
+    except exceptions.TemplateError as ex:
+        _LOGGER.warning(
+            "Error initializing 'template' trigger for '%s': %s",
+            automation_info["name"],
+            ex,
+        )
 
     @callback
     def template_listener(event, updates):
         """Listen for state changes and calls action."""
-        nonlocal delay_cancel
+        nonlocal delay_cancel, armed
         result = updates.pop().result
 
+        if isinstance(result, exceptions.TemplateError):
+            _LOGGER.warning(
+                "Error evaluating 'template' trigger for '%s': %s",
+                automation_info["name"],
+                result,
+            )
+            return
+
         if delay_cancel:
             # pylint: disable=not-callable
             delay_cancel()
             delay_cancel = None
 
         if not result_as_boolean(result):
+            armed = True
             return
 
+        # Only fire when previously armed.
+        if not armed:
+            return
+
+        # Fire!
+        armed = False
+
         entity_id = event and event.data.get("entity_id")
         from_s = event and event.data.get("old_state")
         to_s = event and event.data.get("new_state")
diff --git a/tests/components/template/test_trigger.py b/tests/components/template/test_trigger.py
index de4974cb1b6..3ba79e85bf2 100644
--- a/tests/components/template/test_trigger.py
+++ b/tests/components/template/test_trigger.py
@@ -43,13 +43,15 @@ async def test_if_fires_on_change_bool(hass, calls):
             automation.DOMAIN: {
                 "trigger": {
                     "platform": "template",
-                    "value_template": "{{ states.test.entity.state and true }}",
+                    "value_template": '{{ states.test.entity.state == "world" and true }}',
                 },
                 "action": {"service": "test.automation"},
             }
         },
     )
 
+    assert len(calls) == 0
+
     hass.states.async_set("test.entity", "world")
     await hass.async_block_till_done()
     assert len(calls) == 1
@@ -75,13 +77,15 @@ async def test_if_fires_on_change_str(hass, calls):
             automation.DOMAIN: {
                 "trigger": {
                     "platform": "template",
-                    "value_template": '{{ states.test.entity.state and "true" }}',
+                    "value_template": '{{ states.test.entity.state == "world" and "true" }}',
                 },
                 "action": {"service": "test.automation"},
             }
         },
     )
 
+    assert len(calls) == 0
+
     hass.states.async_set("test.entity", "world")
     await hass.async_block_till_done()
     assert len(calls) == 1
@@ -96,7 +100,7 @@ async def test_if_fires_on_change_str_crazy(hass, calls):
             automation.DOMAIN: {
                 "trigger": {
                     "platform": "template",
-                    "value_template": '{{ states.test.entity.state and "TrUE" }}',
+                    "value_template": '{{ states.test.entity.state == "world" and "TrUE" }}',
                 },
                 "action": {"service": "test.automation"},
             }
@@ -108,6 +112,62 @@ async def test_if_fires_on_change_str_crazy(hass, calls):
     assert len(calls) == 1
 
 
+async def test_if_not_fires_when_true_at_setup(hass, calls):
+    """Test for not firing during startup."""
+    assert await async_setup_component(
+        hass,
+        automation.DOMAIN,
+        {
+            automation.DOMAIN: {
+                "trigger": {
+                    "platform": "template",
+                    "value_template": '{{ states.test.entity.state == "hello" }}',
+                },
+                "action": {"service": "test.automation"},
+            }
+        },
+    )
+
+    assert len(calls) == 0
+
+    hass.states.async_set("test.entity", "hello", force_update=True)
+    await hass.async_block_till_done()
+    assert len(calls) == 0
+
+
+async def test_if_not_fires_because_fail(hass, calls):
+    """Test for not firing after TemplateError."""
+    hass.states.async_set("test.number", "1")
+
+    assert await async_setup_component(
+        hass,
+        automation.DOMAIN,
+        {
+            automation.DOMAIN: {
+                "trigger": {
+                    "platform": "template",
+                    "value_template": "{{ 84 / states.test.number.state|int == 42 }}",
+                },
+                "action": {"service": "test.automation"},
+            }
+        },
+    )
+
+    assert len(calls) == 0
+
+    hass.states.async_set("test.number", "2")
+    await hass.async_block_till_done()
+    assert len(calls) == 1
+
+    hass.states.async_set("test.number", "0")
+    await hass.async_block_till_done()
+    assert len(calls) == 1
+
+    hass.states.async_set("test.number", "2")
+    await hass.async_block_till_done()
+    assert len(calls) == 1
+
+
 async def test_if_not_fires_on_change_bool(hass, calls):
     """Test for not firing on boolean change."""
     assert await async_setup_component(
@@ -117,7 +177,7 @@ async def test_if_not_fires_on_change_bool(hass, calls):
             automation.DOMAIN: {
                 "trigger": {
                     "platform": "template",
-                    "value_template": "{{ states.test.entity.state and false }}",
+                    "value_template": '{{ states.test.entity.state == "world" and false }}',
                 },
                 "action": {"service": "test.automation"},
             }
@@ -198,7 +258,7 @@ async def test_if_fires_on_two_change(hass, calls):
             automation.DOMAIN: {
                 "trigger": {
                     "platform": "template",
-                    "value_template": "{{ states.test.entity.state and true }}",
+                    "value_template": "{{ states.test.entity.state == 'world' }}",
                 },
                 "action": {"service": "test.automation"},
             }