diff --git a/.github/workflows/release-drafter.yml b/.github/workflows/release-drafter.yml
index ca45aa1..e71bc75 100644
--- a/.github/workflows/release-drafter.yml
+++ b/.github/workflows/release-drafter.yml
@@ -1,5 +1,8 @@
 name: Release Drafter
 
+permissions:
+  contents: read
+
 on:
   push:
     branches:
@@ -9,6 +12,9 @@ on:
 
 jobs:
   update_release_draft:
+    permissions:
+      contents: write
+      pull-requests: write
     name: Update release draft
     runs-on: ubuntu-latest
     steps:
@@ -19,6 +25,6 @@ jobs:
       - name: Create Release
         uses: release-drafter/release-drafter@v6
         with:
-          disable-releaser: github.ref != 'refs/heads/main'
+          commitish: refs/heads/main
         env:
           GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
diff --git a/custom_components/state_webhook/__init__.py b/custom_components/state_webhook/__init__.py
index 48698e2..3378285 100644
--- a/custom_components/state_webhook/__init__.py
+++ b/custom_components/state_webhook/__init__.py
@@ -1,3 +1,4 @@
+import asyncio
 import fnmatch
 import logging
 from collections.abc import Mapping
@@ -19,14 +20,18 @@
     CONF_FILTER_MODE,
     CONF_PAYLOAD_ATTRIBUTES,
     CONF_PAYLOAD_OLD_STATE,
+    CONF_RETRY_LIMIT,
     CONF_WEBHOOK_AUTH_HEADER,
     CONF_WEBHOOK_HEADERS,
     CONF_WEBHOOK_URL,
+    DEFAULT_RETRY_LIMIT,
     FilterMode,
 )
 
 _LOGGER = logging.getLogger(__name__)
 
+RETRY_DELAY = 5
+
 
 async def async_setup_entry(hass: HomeAssistant, entry: ConfigEntry) -> bool:
     async def _register_webhook(_: Any) -> None:  # noqa ANN401
@@ -47,6 +52,7 @@ async def register_webhook(hass: HomeAssistant, entry: ConfigEntry) -> None:
 
     webhook_url = str(entry.options.get(CONF_WEBHOOK_URL))
     headers = prepare_headers(entry.options)
+    retry_limit = int(entry.options.get(CONF_RETRY_LIMIT, DEFAULT_RETRY_LIMIT))
 
     _LOGGER.debug("Start webhook tracking using URL: %s", webhook_url)
     _LOGGER.debug("Tracking the following entities: %s", entities_to_track)
@@ -76,12 +82,17 @@ async def handle_state_change(event: Event[EventStateChangedData]) -> None:
             new_state.state,
         )
 
-        await call_webhook(
-            session,
-            webhook_url,
-            headers,
-            build_payload(entry.options, entity_id, old_state, new_state),
-        )
+        result = False
+        retry_count = 0
+        while not result and retry_count < retry_limit:
+            result = await call_webhook(
+                session,
+                webhook_url,
+                headers,
+                build_payload(entry.options, entity_id, old_state, new_state),
+            )
+            retry_count += 1
+            await asyncio.sleep(RETRY_DELAY)
 
     async_track_state_change_event(hass, entities_to_track, handle_state_change)
 
diff --git a/custom_components/state_webhook/config_flow.py b/custom_components/state_webhook/config_flow.py
index 04ddb72..b4b7e10 100644
--- a/custom_components/state_webhook/config_flow.py
+++ b/custom_components/state_webhook/config_flow.py
@@ -20,6 +20,9 @@
     EntitySelectorConfig,
     LabelSelector,
     LabelSelectorConfig,
+    NumberSelector,
+    NumberSelectorConfig,
+    NumberSelectorMode,
     ObjectSelector,
     SelectSelector,
     SelectSelectorConfig,
@@ -35,9 +38,11 @@
     CONF_ENTITY_LABELS,
     CONF_PAYLOAD_ATTRIBUTES,
     CONF_PAYLOAD_OLD_STATE,
+    CONF_RETRY_LIMIT,
     CONF_WEBHOOK_AUTH_HEADER,
     CONF_WEBHOOK_HEADERS,
     CONF_WEBHOOK_URL,
+    DEFAULT_RETRY_LIMIT,
     DOMAIN,
     FilterMode,
 )
@@ -47,6 +52,7 @@
         vol.Required(CONF_WEBHOOK_URL): TextSelector(),
         vol.Optional(CONF_WEBHOOK_AUTH_HEADER): TextSelector(),
         vol.Optional(CONF_WEBHOOK_HEADERS): ObjectSelector(),
+        vol.Optional(CONF_RETRY_LIMIT, default=DEFAULT_RETRY_LIMIT): NumberSelector(NumberSelectorConfig(mode=NumberSelectorMode.BOX)),
     },
 )
 
diff --git a/custom_components/state_webhook/const.py b/custom_components/state_webhook/const.py
index 17ee22f..851bd9c 100644
--- a/custom_components/state_webhook/const.py
+++ b/custom_components/state_webhook/const.py
@@ -9,10 +9,13 @@
 CONF_FILTER_MODE = "filter_mode"
 CONF_PAYLOAD_ATTRIBUTES = "payload_attributes"
 CONF_PAYLOAD_OLD_STATE = "payload_old_state"
+CONF_RETRY_LIMIT = "retry_limit"
 CONF_WEBHOOK_URL = "webhook_url"
 CONF_WEBHOOK_HEADERS = "webhook_headers"
 CONF_WEBHOOK_AUTH_HEADER = "webhook_auth_header"
 
+DEFAULT_RETRY_LIMIT = 3
+
 class FilterMode(StrEnum):
     OR = "or"
     AND = "and"
diff --git a/custom_components/state_webhook/translations/en.json b/custom_components/state_webhook/translations/en.json
index 2ad077f..cf21a7c 100644
--- a/custom_components/state_webhook/translations/en.json
+++ b/custom_components/state_webhook/translations/en.json
@@ -4,11 +4,13 @@
       "user": {
         "data": {
           "name": "Name",
+          "retry_limit": "Retry limit",
           "webhook_url": "Webhook URL",
           "webhook_auth_header": "Authorization header",
           "webhook_headers": "Additional headers"
         },
         "data_description": {
+          "retry_limit": "Number of times to retry sending the webhook, with a delay of 5 seconds between each retry",
           "webhook_url": "URL where state changes will be sent to using POST request",
           "webhook_auth_header": "Authorization header to be sent with the request",
           "webhook_headers": "Additional headers to be sent. Format: key1: value1 on each line"
@@ -48,11 +50,13 @@
       "webhook": {
         "data": {
           "name": "Name",
+          "retry_limit": "Retry limit",
           "webhook_url": "Webhook URL",
           "webhook_auth_header": "Authorization header",
           "webhook_headers": "Additional headers"
         },
         "data_description": {
+          "retry_limit": "Number of times to retry sending the webhook, with a delay of 5 seconds between each retry",
           "webhook_url": "URL where state changes will be sent to using POST request",
           "webhook_auth_header": "Authorization header to be sent with the request",
           "webhook_headers": "Additional headers to be sent. Format: key1: value1 on each line"
diff --git a/tests/conftest.py b/tests/conftest.py
index 1ca4d8c..c35705e 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -1,5 +1,6 @@
 import asyncio
 from collections.abc import Generator
+from unittest.mock import patch
 
 import pytest
 from homeassistant import loader
@@ -50,3 +51,9 @@ def device_reg(hass: HomeAssistant) -> DeviceRegistry:
 def entity_reg(hass: HomeAssistant) -> EntityRegistry:
     """Return an empty, loaded, registry."""
     return mock_registry(hass)
+
+
+@pytest.fixture(autouse=True)
+def patch_retry_delay() -> Generator:
+    with patch("custom_components.state_webhook.RETRY_DELAY", 0):
+        yield
diff --git a/tests/test_config_flow.py b/tests/test_config_flow.py
index e4decb1..9379c0a 100644
--- a/tests/test_config_flow.py
+++ b/tests/test_config_flow.py
@@ -11,9 +11,16 @@
 from homeassistant.helpers.schema_config_entry_flow import SchemaFlowError
 from pytest_homeassistant_custom_component.common import MockConfigEntry
 
-from custom_components.state_webhook import CONF_ENTITY_DOMAIN, CONF_ENTITY_ID, CONF_FILTER_MODE, CONF_PAYLOAD_OLD_STATE, CONF_WEBHOOK_URL
+from custom_components.state_webhook import (
+    CONF_ENTITY_DOMAIN,
+    CONF_ENTITY_ID,
+    CONF_FILTER_MODE,
+    CONF_PAYLOAD_OLD_STATE,
+    CONF_RETRY_LIMIT,
+    CONF_WEBHOOK_URL,
+)
 from custom_components.state_webhook.config_flow import validate_webhook
-from custom_components.state_webhook.const import CONF_PAYLOAD_ATTRIBUTES, DOMAIN, FilterMode
+from custom_components.state_webhook.const import CONF_PAYLOAD_ATTRIBUTES, DEFAULT_RETRY_LIMIT, DOMAIN, FilterMode
 
 
 async def test_validate_url() -> None:
@@ -85,6 +92,7 @@ async def test_config_flow(hass: HomeAssistant) -> None:
         assert result["options"] == {
             CONF_PAYLOAD_ATTRIBUTES: True,
             CONF_PAYLOAD_OLD_STATE: True,
+            CONF_RETRY_LIMIT: DEFAULT_RETRY_LIMIT,
             CONF_NAME: "Test",
             CONF_WEBHOOK_URL: "http://example.com",
             CONF_FILTER_MODE: FilterMode.OR,
diff --git a/tests/test_init.py b/tests/test_init.py
index 0c38d2f..a2c53cb 100644
--- a/tests/test_init.py
+++ b/tests/test_init.py
@@ -9,7 +9,7 @@
 from homeassistant.helpers.entity_registry import RegistryEntry
 from pytest_homeassistant_custom_component.common import MockConfigEntry, mock_registry
 
-from custom_components.state_webhook import CONF_ENTITY_DOMAIN, CONF_WEBHOOK_URL, async_setup_entry, build_payload
+from custom_components.state_webhook import CONF_ENTITY_DOMAIN, CONF_ENTITY_ID, CONF_WEBHOOK_URL, async_setup_entry, build_payload
 from custom_components.state_webhook.const import CONF_PAYLOAD_ATTRIBUTES, CONF_PAYLOAD_OLD_STATE, DOMAIN
 
 DEFAULT_WEBHOOK_URL = "https://example.com/webhook"
@@ -59,6 +59,30 @@ async def test_state_webhook_triggered_successfully(hass: HomeAssistant) -> None
             headers={},
         )
 
+async def test_retry_when_webhook_unavailable(hass: HomeAssistant) -> None:
+    hass.states.async_set("input_boolean.test", "off")
+    await hass.async_block_till_done()
+
+    entry = MockConfigEntry(
+        domain=DOMAIN,
+        options={
+            CONF_WEBHOOK_URL: DEFAULT_WEBHOOK_URL,
+            CONF_ENTITY_ID: ["input_boolean.test"],
+        },
+    )
+
+    await async_setup_entry(hass, entry)
+
+    with aioresponses() as http_mock:
+        http_mock.post(DEFAULT_WEBHOOK_URL, status=500, repeat=2)
+        http_mock.post(DEFAULT_WEBHOOK_URL, status=200)
+
+        hass.states.async_set("input_boolean.test", "on")
+        await hass.async_block_till_done()
+
+        total_calls = sum(len(calls) for calls in http_mock.requests.values())
+        assert total_calls == 3
+
 
 @pytest.mark.parametrize(
     "options,expected_payload",