diff --git a/api/conftest.py b/api/conftest.py
index ab0aa198e9e3..ff6732ee44d3 100644
--- a/api/conftest.py
+++ b/api/conftest.py
@@ -1018,14 +1018,20 @@ def flagsmith_environments_v2_table(dynamodb: DynamoDBServiceResource) -> Table:
 
 
 @pytest.fixture()
-def feature_external_resource(
-    feature: Feature, post_request_mock: MagicMock, mocker: MockerFixture
-) -> FeatureExternalResource:
-    mocker.patch(
+def mock_github_client_generate_token(mocker: MockerFixture) -> MagicMock:
+    return mocker.patch(
         "integrations.github.client.generate_token",
         return_value="mocked_token",
     )
 
+
+@pytest.fixture()
+def feature_external_resource(
+    feature: Feature,
+    post_request_mock: MagicMock,
+    mocker: MockerFixture,
+    mock_github_client_generate_token: MagicMock,
+) -> FeatureExternalResource:
     return FeatureExternalResource.objects.create(
         url="https://github.com/repositoryownertest/repositorynametest/issues/11",
         type="GITHUB_ISSUE",
@@ -1035,16 +1041,26 @@ def feature_external_resource(
 
 
 @pytest.fixture()
-def feature_with_value_external_resource(
-    feature_with_value: Feature,
+def feature_external_resource_gh_pr(
+    feature: Feature,
     post_request_mock: MagicMock,
     mocker: MockerFixture,
+    mock_github_client_generate_token: MagicMock,
 ) -> FeatureExternalResource:
-    mocker.patch(
-        "integrations.github.client.generate_token",
-        return_value="mocked_token",
+    return FeatureExternalResource.objects.create(
+        url="https://github.com/repositoryownertest/repositorynametest/pull/1",
+        type="GITHUB_PR",
+        feature=feature,
+        metadata='{"status": "open"}',
     )
 
+
+@pytest.fixture()
+def feature_with_value_external_resource(
+    feature_with_value: Feature,
+    post_request_mock: MagicMock,
+    mock_github_client_generate_token: MagicMock,
+) -> FeatureExternalResource:
     return FeatureExternalResource.objects.create(
         url="https://github.com/repositoryownertest/repositorynametest/issues/11",
         type="GITHUB_ISSUE",
@@ -1069,6 +1085,7 @@ def github_repository(
         repository_owner="repositoryownertest",
         repository_name="repositorynametest",
         project=project,
+        tagging_enabled=True,
     )
 
 
@@ -1120,3 +1137,10 @@ def handle(self, record: logging.LogRecord) -> None:
             self.messages.append(self.format(record))
 
     return InspectingHandler()
+
+
+@pytest.fixture
+def set_github_webhook_secret() -> None:
+    from django.conf import settings
+
+    settings.GITHUB_WEBHOOK_SECRET = "secret-key"
diff --git a/api/features/feature_external_resources/models.py b/api/features/feature_external_resources/models.py
index 6dcfc4d99a7f..8df2428e3158 100644
--- a/api/features/feature_external_resources/models.py
+++ b/api/features/feature_external_resources/models.py
@@ -1,3 +1,4 @@
+import json
 import logging
 
 from django.db import models
@@ -11,9 +12,11 @@
 
 from environments.models import Environment
 from features.models import Feature, FeatureState
+from integrations.github.constants import GitHubEventType, GitHubTag
 from integrations.github.github import call_github_task
+from integrations.github.models import GithubRepository
 from organisations.models import Organisation
-from webhooks.webhooks import WebhookEventType
+from projects.tags.models import Tag, TagType
 
 logger = logging.getLogger(__name__)
 
@@ -24,6 +27,20 @@ class ResourceType(models.TextChoices):
     GITHUB_PR = "GITHUB_PR", "GitHub PR"
 
 
+tag_by_type_and_state = {
+    ResourceType.GITHUB_ISSUE.value: {
+        "open": GitHubTag.ISSUE_OPEN.value,
+        "closed": GitHubTag.ISSUE_CLOSED.value,
+    },
+    ResourceType.GITHUB_PR.value: {
+        "open": GitHubTag.PR_OPEN.value,
+        "closed": GitHubTag.PR_CLOSED.value,
+        "merged": GitHubTag.PR_MERGED.value,
+        "draft": GitHubTag.PR_DRAFT.value,
+    },
+}
+
+
 class FeatureExternalResource(LifecycleModelMixin, models.Model):
     url = models.URLField()
     type = models.CharField(max_length=20, choices=ResourceType.choices)
@@ -49,12 +66,33 @@ class Meta:
 
     @hook(AFTER_SAVE)
     def execute_after_save_actions(self):
+        # Tag the feature with the external resource type
+        metadata = json.loads(self.metadata) if self.metadata else {}
+        state = metadata.get("state", "open")
+
         # Add a comment to GitHub Issue/PR when feature is linked to the GH external resource
+        # and tag the feature with the corresponding tag if tagging is enabled
         if (
-            Organisation.objects.prefetch_related("github_config")
+            github_configuration := Organisation.objects.prefetch_related(
+                "github_config"
+            )
             .get(id=self.feature.project.organisation_id)
             .github_config.first()
         ):
+            github_repo = GithubRepository.objects.get(
+                github_configuration=github_configuration.id,
+                project=self.feature.project,
+            )
+            if github_repo.tagging_enabled:
+                github_tag = Tag.objects.get(
+                    label=tag_by_type_and_state[self.type][state],
+                    project=self.feature.project,
+                    is_system_tag=True,
+                    type=TagType.GITHUB.value,
+                )
+                self.feature.tags.add(github_tag)
+                self.feature.save()
+
             feature_states: list[FeatureState] = []
 
             environments = Environment.objects.filter(
@@ -74,7 +112,7 @@ def execute_after_save_actions(self):
 
             call_github_task(
                 organisation_id=self.feature.project.organisation_id,
-                type=WebhookEventType.FEATURE_EXTERNAL_RESOURCE_ADDED.value,
+                type=GitHubEventType.FEATURE_EXTERNAL_RESOURCE_ADDED.value,
                 feature=self.feature,
                 segment_name=None,
                 url=None,
@@ -92,7 +130,7 @@ def execute_before_save_actions(self) -> None:
 
             call_github_task(
                 organisation_id=self.feature.project.organisation_id,
-                type=WebhookEventType.FEATURE_EXTERNAL_RESOURCE_REMOVED.value,
+                type=GitHubEventType.FEATURE_EXTERNAL_RESOURCE_REMOVED.value,
                 feature=self.feature,
                 segment_name=None,
                 url=self.url,
diff --git a/api/features/feature_external_resources/views.py b/api/features/feature_external_resources/views.py
index c9636bba1132..641074215fe6 100644
--- a/api/features/feature_external_resources/views.py
+++ b/api/features/feature_external_resources/views.py
@@ -1,10 +1,16 @@
+import re
+
 from django.shortcuts import get_object_or_404
 from rest_framework import status, viewsets
 from rest_framework.response import Response
 
 from features.models import Feature
 from features.permissions import FeatureExternalResourcePermissions
-from integrations.github.client import get_github_issue_pr_title_and_state
+from integrations.github.client import (
+    get_github_issue_pr_title_and_state,
+    label_github_issue_pr,
+)
+from integrations.github.models import GithubRepository
 from organisations.models import Organisation
 
 from .models import FeatureExternalResource
@@ -48,14 +54,13 @@ def create(self, request, *args, **kwargs):
             ),
         )
 
-        if not (
-            (
-                Organisation.objects.prefetch_related("github_config")
-                .get(id=feature.project.organisation_id)
-                .github_config.first()
-            )
-            or not hasattr(feature.project, "github_project")
-        ):
+        github_configuration = (
+            Organisation.objects.prefetch_related("github_config")
+            .get(id=feature.project.organisation_id)
+            .github_config.first()
+        )
+
+        if not github_configuration or not hasattr(feature.project, "github_project"):
             return Response(
                 data={
                     "detail": "This Project doesn't have a valid GitHub integration configuration"
@@ -63,7 +68,42 @@ def create(self, request, *args, **kwargs):
                 content_type="application/json",
                 status=status.HTTP_400_BAD_REQUEST,
             )
-        return super().create(request, *args, **kwargs)
+
+        # Get repository owner and name, and issue/PR number from the external resource URL
+        url = request.data.get("url")
+        if request.data.get("type") == "GITHUB_PR":
+            pattern = r"github.com/([^/]+)/([^/]+)/pull/(\d+)$"
+        elif request.data.get("type") == "GITHUB_ISSUE":
+            pattern = r"github.com/([^/]+)/([^/]+)/issues/(\d+)$"
+        else:
+            return Response(
+                data={"detail": "Incorrect GitHub type"},
+                content_type="application/json",
+                status=status.HTTP_400_BAD_REQUEST,
+            )
+
+        match = re.search(pattern, url)
+        if match:
+            owner, repo, issue = match.groups()
+            if GithubRepository.objects.get(
+                github_configuration=github_configuration,
+                repository_owner=owner,
+                repository_name=repo,
+            ).tagging_enabled:
+                label_github_issue_pr(
+                    installation_id=github_configuration.installation_id,
+                    owner=owner,
+                    repo=repo,
+                    issue=issue,
+                )
+            response = super().create(request, *args, **kwargs)
+            return response
+        else:
+            return Response(
+                data={"detail": "Invalid GitHub Issue/PR URL"},
+                content_type="application/json",
+                status=status.HTTP_400_BAD_REQUEST,
+            )
 
     def perform_update(self, serializer):
         external_resource_id = int(self.kwargs["pk"])
diff --git a/api/features/models.py b/api/features/models.py
index 6a80c5c90251..1493a54c4849 100644
--- a/api/features/models.py
+++ b/api/features/models.py
@@ -74,6 +74,7 @@
     STRING,
 )
 from features.versioning.models import EnvironmentFeatureVersion
+from integrations.github.constants import GitHubEventType
 from metadata.models import Metadata
 from projects.models import Project
 from projects.tags.models import Tag
@@ -139,7 +140,6 @@ class Meta:
     @hook(AFTER_SAVE)
     def create_github_comment(self) -> None:
         from integrations.github.github import call_github_task
-        from webhooks.webhooks import WebhookEventType
 
         if (
             self.external_resources.exists()
@@ -150,7 +150,7 @@ def create_github_comment(self) -> None:
 
             call_github_task(
                 organisation_id=self.project.organisation_id,
-                type=WebhookEventType.FLAG_DELETED.value,
+                type=GitHubEventType.FLAG_DELETED.value,
                 feature=self,
                 segment_name=None,
                 url=None,
@@ -406,7 +406,6 @@ def _get_environment(self) -> "Environment":
     @hook(AFTER_DELETE)
     def create_github_comment(self) -> None:
         from integrations.github.github import call_github_task
-        from webhooks.webhooks import WebhookEventType
 
         if (
             self.feature.external_resources.exists()
@@ -416,7 +415,7 @@ def create_github_comment(self) -> None:
 
             call_github_task(
                 self.feature.project.organisation_id,
-                WebhookEventType.SEGMENT_OVERRIDE_DELETED.value,
+                GitHubEventType.SEGMENT_OVERRIDE_DELETED.value,
                 self.feature,
                 self.segment.name,
                 None,
diff --git a/api/features/serializers.py b/api/features/serializers.py
index a2a297238637..5d4de0005517 100644
--- a/api/features/serializers.py
+++ b/api/features/serializers.py
@@ -19,6 +19,7 @@
 from environments.sdk.serializers_mixins import (
     HideSensitiveFieldsSerializerMixin,
 )
+from integrations.github.constants import GitHubEventType
 from integrations.github.github import call_github_task
 from metadata.serializers import MetadataSerializer, SerializerWithMetadata
 from projects.models import Project
@@ -30,7 +31,6 @@
 from util.drf_writable_nested.serializers import (
     DeleteBeforeUpdateWritableNestedModelSerializer,
 )
-from webhooks.webhooks import WebhookEventType
 
 from .constants import INTERSECTION, UNION
 from .feature_segments.serializers import (
@@ -478,7 +478,7 @@ def save(self, **kwargs):
 
                 call_github_task(
                     organisation_id=feature_state.feature.project.organisation_id,
-                    type=WebhookEventType.FLAG_UPDATED.value,
+                    type=GitHubEventType.FLAG_UPDATED.value,
                     feature=feature_state.feature,
                     segment_name=None,
                     url=None,
diff --git a/api/features/versioning/serializers.py b/api/features/versioning/serializers.py
index ec21cdfae5ae..90295f222b8a 100644
--- a/api/features/versioning/serializers.py
+++ b/api/features/versioning/serializers.py
@@ -8,10 +8,10 @@
     CustomCreateSegmentOverrideFeatureStateSerializer,
 )
 from features.versioning.models import EnvironmentFeatureVersion
+from integrations.github.constants import GitHubEventType
 from integrations.github.github import call_github_task
 from segments.models import Segment
 from users.models import FFAdminUser
-from webhooks.webhooks import WebhookEventType
 
 
 class CustomEnvironmentFeatureVersionFeatureStateSerializer(
@@ -36,7 +36,7 @@ def save(self, **kwargs):
 
             call_github_task(
                 organisation_id=feature_state.environment.project.organisation_id,
-                type=WebhookEventType.FLAG_UPDATED.value,
+                type=GitHubEventType.FLAG_UPDATED.value,
                 feature=feature_state.feature,
                 segment_name=None,
                 url=None,
diff --git a/api/integrations/github/client.py b/api/integrations/github/client.py
index b4307fd736f9..4d4293b30a48 100644
--- a/api/integrations/github/client.py
+++ b/api/integrations/github/client.py
@@ -1,3 +1,4 @@
+import json
 import logging
 from enum import Enum
 from typing import Any
@@ -5,11 +6,15 @@
 import requests
 from django.conf import settings
 from github import Auth, Github
+from requests.exceptions import HTTPError
 
 from integrations.github.constants import (
     GITHUB_API_CALLS_TIMEOUT,
     GITHUB_API_URL,
     GITHUB_API_VERSION,
+    GITHUB_FLAGSMITH_LABEL,
+    GITHUB_FLAGSMITH_LABEL_COLOR,
+    GITHUB_FLAGSMITH_LABEL_DESCRIPTION,
 )
 from integrations.github.dataclasses import (
     IssueQueryParams,
@@ -159,6 +164,9 @@ def fetch_search_github_resource(
             "id": i["id"],
             "title": i["title"],
             "number": i["number"],
+            "state": i["state"],
+            "merged": i.get("merged", False),
+            "draft": i.get("draft", False),
         }
         for i in json_response["items"]
     ]
@@ -244,3 +252,45 @@ def fetch_github_repo_contributors(
     ]
 
     return build_paginated_response(results, response)
+
+
+def create_flagsmith_flag_label(
+    installation_id: str, owner: str, repo: str
+) -> dict[str, Any]:
+    # Create "Flagsmith Flag" label in linked repo
+    url = f"{GITHUB_API_URL}repos/{owner}/{repo}/labels"
+    headers = build_request_headers(installation_id)
+    payload = {
+        "name": GITHUB_FLAGSMITH_LABEL,
+        "color": GITHUB_FLAGSMITH_LABEL_COLOR,
+        "description": GITHUB_FLAGSMITH_LABEL_DESCRIPTION,
+    }
+    try:
+        response = requests.post(
+            url, json=payload, headers=headers, timeout=GITHUB_API_CALLS_TIMEOUT
+        )
+        response.raise_for_status()
+        return response.json()
+
+    except HTTPError:
+        response_content = response.content.decode("utf-8")
+        error_data = json.loads(response_content)
+        if any(
+            error["code"] == "already_exists" for error in error_data.get("errors", [])
+        ):
+            logger.warning("Label already exists")
+            return {"message": "Label already exists"}, 200
+
+
+def label_github_issue_pr(
+    installation_id: str, owner: str, repo: str, issue: str
+) -> dict[str, Any]:
+    # Label linked GitHub Issue or PR with the "Flagsmith Flag" label
+    url = f"{GITHUB_API_URL}repos/{owner}/{repo}/issues/{issue}/labels"
+    headers = build_request_headers(installation_id)
+    payload = [GITHUB_FLAGSMITH_LABEL]
+    response = requests.post(
+        url, json=payload, headers=headers, timeout=GITHUB_API_CALLS_TIMEOUT
+    )
+    response.raise_for_status()
+    return response.json()
diff --git a/api/integrations/github/constants.py b/api/integrations/github/constants.py
index 929ea690b87e..897b3a2c6725 100644
--- a/api/integrations/github/constants.py
+++ b/api/integrations/github/constants.py
@@ -1,3 +1,5 @@
+from enum import Enum
+
 GITHUB_API_URL = "https://api.github.com/"
 GITHUB_API_VERSION = "2022-11-28"
 
@@ -7,11 +9,49 @@
 | :--- | :----- | :------ | :------ |\n"""
 FEATURE_TABLE_ROW = "| [%s](%s) | %s | %s | %s |\n"
 LINK_SEGMENT_TITLE = "Segment `%s` values:\n"
-UNLINKED_FEATURE_TEXT = "### The feature flag `%s` was unlinked from the issue/PR"
-UPDATED_FEATURE_TEXT = "Flagsmith Feature `%s` has been updated:\n"
-DELETED_FEATURE_TEXT = "### The Feature Flag `%s` was deleted"
+UNLINKED_FEATURE_TEXT = "**The feature flag `%s` was unlinked from the issue/PR**"
+UPDATED_FEATURE_TEXT = "**Flagsmith Feature `%s` has been updated:**\n"
+FEATURE_UPDATED_FROM_GHA_TEXT = (
+    "**Flagsmith Feature `%s` has been updated from GHA:**\n"
+)
+DELETED_FEATURE_TEXT = "**The Feature Flag `%s` was deleted**"
 DELETED_SEGMENT_OVERRIDE_TEXT = (
-    "### The Segment Override `%s` for Feature Flag `%s` was deleted"
+    "**The Segment Override `%s` for Feature Flag `%s` was deleted**"
 )
 FEATURE_ENVIRONMENT_URL = "%s/project/%s/environment/%s/features?feature=%s&tab=%s"
 GITHUB_API_CALLS_TIMEOUT = 10
+
+GITHUB_TAG_COLOR = "#838992"
+GITHUB_FLAGSMITH_LABEL = "Flagsmith Flag"
+GITHUB_FLAGSMITH_LABEL_DESCRIPTION = (
+    "This GitHub Issue/PR is linked to a Flagsmith Feature Flag"
+)
+GITHUB_FLAGSMITH_LABEL_COLOR = "6633FF"
+
+
+class GitHubEventType(Enum):
+    FLAG_UPDATED = "FLAG_UPDATED"
+    FLAG_DELETED = "FLAG_DELETED"
+    FLAG_UPDATED_FROM_GHA = "FLAG_UPDATED_FROM_GHA"
+    FEATURE_EXTERNAL_RESOURCE_ADDED = "FEATURE_EXTERNAL_RESOURCE_ADDED"
+    FEATURE_EXTERNAL_RESOURCE_REMOVED = "FEATURE_EXTERNAL_RESOURCE_REMOVED"
+    SEGMENT_OVERRIDE_DELETED = "SEGMENT_OVERRIDE_DELETED"
+
+
+class GitHubTag(Enum):
+    PR_OPEN = "PR Open"
+    PR_MERGED = "PR Merged"
+    PR_CLOSED = "PR Closed"
+    PR_DRAFT = "PR Draft"
+    ISSUE_OPEN = "Issue Open"
+    ISSUE_CLOSED = "Issue Closed"
+
+
+github_tag_description = {
+    GitHubTag.PR_OPEN.value: "This feature has a linked PR open",
+    GitHubTag.PR_MERGED.value: "This feature has a linked PR merged",
+    GitHubTag.PR_CLOSED.value: "This feature has a linked PR closed",
+    GitHubTag.PR_DRAFT.value: "This feature has a linked PR draft",
+    GitHubTag.ISSUE_OPEN.value: "This feature has a linked issue open",
+    GitHubTag.ISSUE_CLOSED.value: "This feature has a linked issue closed",
+}
diff --git a/api/integrations/github/github.py b/api/integrations/github/github.py
index ddbbdcc04698..6b3573903dde 100644
--- a/api/integrations/github/github.py
+++ b/api/integrations/github/github.py
@@ -4,6 +4,7 @@
 from typing import Any
 
 from core.helpers import get_current_site_url
+from django.db.models import Q
 from django.utils.formats import get_format
 
 from features.models import Feature, FeatureState, FeatureStateValue
@@ -17,14 +18,69 @@
     LINK_SEGMENT_TITLE,
     UNLINKED_FEATURE_TEXT,
     UPDATED_FEATURE_TEXT,
+    GitHubEventType,
+    GitHubTag,
 )
 from integrations.github.dataclasses import GithubData
 from integrations.github.models import GithubConfiguration
 from integrations.github.tasks import call_github_app_webhook_for_feature_state
-from webhooks.webhooks import WebhookEventType
+from projects.tags.models import Tag, TagType
 
 logger = logging.getLogger(__name__)
 
+tag_by_event_type = {
+    "pull_request": {
+        "closed": GitHubTag.PR_CLOSED.value,
+        "converted_to_draft": GitHubTag.PR_DRAFT.value,
+        "opened": GitHubTag.PR_OPEN.value,
+        "reopened": GitHubTag.PR_OPEN.value,
+        "ready_for_review": GitHubTag.PR_OPEN.value,
+        "merged": GitHubTag.PR_MERGED.value,
+    },
+    "issues": {
+        "closed": GitHubTag.ISSUE_CLOSED.value,
+        "opened": GitHubTag.ISSUE_OPEN.value,
+        "reopened": GitHubTag.ISSUE_OPEN.value,
+    },
+}
+
+
+def tag_feature_per_github_event(
+    event_type: str, action: str, metadata: dict[str, Any]
+) -> None:
+
+    # Get Feature with external resource of type GITHUB and url matching the resource URL
+    feature = Feature.objects.filter(
+        Q(external_resources__type="GITHUB_PR")
+        | Q(external_resources__type="GITHUB_ISSUE"),
+        external_resources__url=metadata.get("html_url"),
+    ).first()
+
+    if feature:
+        if (
+            event_type == "pull_request"
+            and action == "closed"
+            and metadata.get("merged")
+        ):
+            action = "merged"
+        # Get corresponding project Tag to tag the feature
+        github_tag = Tag.objects.get(
+            label=tag_by_event_type[event_type][action],
+            project=feature.project_id,
+            is_system_tag=True,
+            type=TagType.GITHUB.value,
+        )
+        tag_label_pattern = "Issue" if event_type == "issues" else "PR"
+        # Remove all GITHUB tags from the feature which label starts with issue or pr depending on event_type
+        feature.tags.remove(
+            *feature.tags.filter(
+                Q(type=TagType.GITHUB.value) & Q(label__startswith=tag_label_pattern)
+            )
+        )
+
+        feature.tags.add(github_tag)
+        feature.save()
+
 
 def handle_installation_deleted(payload: dict[str, Any]) -> None:
     installation_id = payload.get("installation", {}).get("id")
@@ -42,6 +98,10 @@ def handle_installation_deleted(payload: dict[str, Any]) -> None:
 def handle_github_webhook_event(event_type: str, payload: dict[str, Any]) -> None:
     if event_type == "installation" and payload.get("action") == "deleted":
         handle_installation_deleted(payload)
+    elif event_type in tag_by_event_type:
+        action = str(payload.get("action"))
+        metadata = payload.get("issue", {}) or payload.get("pull_request", {})
+        tag_feature_per_github_event(event_type, action, metadata)
 
 
 def generate_body_comment(
@@ -53,13 +113,12 @@ def generate_body_comment(
     segment_name: str | None = None,
 ) -> str:
 
-    is_update = event_type == WebhookEventType.FLAG_UPDATED.value
-    is_removed = event_type == WebhookEventType.FEATURE_EXTERNAL_RESOURCE_REMOVED.value
+    is_removed = event_type == GitHubEventType.FEATURE_EXTERNAL_RESOURCE_REMOVED.value
     is_segment_override_deleted = (
-        event_type == WebhookEventType.SEGMENT_OVERRIDE_DELETED.value
+        event_type == GitHubEventType.SEGMENT_OVERRIDE_DELETED.value
     )
 
-    if event_type == WebhookEventType.FLAG_DELETED.value:
+    if event_type == GitHubEventType.FLAG_DELETED.value:
         return DELETED_FEATURE_TEXT % (name)
 
     if is_removed:
@@ -68,7 +127,12 @@ def generate_body_comment(
     if is_segment_override_deleted and segment_name is not None:
         return DELETED_SEGMENT_OVERRIDE_TEXT % (segment_name, name)
 
-    result = UPDATED_FEATURE_TEXT % (name) if is_update else LINK_FEATURE_TITLE % (name)
+    result = ""
+    if event_type == GitHubEventType.FLAG_UPDATED.value:
+        result = UPDATED_FEATURE_TEXT % (name)
+    else:
+        result = LINK_FEATURE_TITLE % (name)
+
     last_segment_name = ""
     if len(feature_states) > 0 and not feature_states[0].get("segment_name"):
         result += FEATURE_TABLE_HEADER
@@ -125,7 +189,7 @@ def generate_data(
             if check_not_none(feature_state_value):
                 feature_env_data["feature_state_value"] = feature_state_value
 
-            if type is not WebhookEventType.FEATURE_EXTERNAL_RESOURCE_REMOVED.value:
+            if type is not GitHubEventType.FEATURE_EXTERNAL_RESOURCE_REMOVED.value:
                 feature_env_data["environment_name"] = feature_state.environment.name
                 feature_env_data["enabled"] = feature_state.enabled
                 feature_env_data["last_updated"] = feature_state.updated_at.strftime(
@@ -150,7 +214,7 @@ def generate_data(
         type=type,
         url=(
             url
-            if type == WebhookEventType.FEATURE_EXTERNAL_RESOURCE_REMOVED.value
+            if type == GitHubEventType.FEATURE_EXTERNAL_RESOURCE_REMOVED.value
             else None
         ),
         feature_states=feature_states_list if feature_states else None,
diff --git a/api/integrations/github/migrations/0004_githubrepository_tagging_enabled.py b/api/integrations/github/migrations/0004_githubrepository_tagging_enabled.py
new file mode 100644
index 000000000000..a3ded07330d2
--- /dev/null
+++ b/api/integrations/github/migrations/0004_githubrepository_tagging_enabled.py
@@ -0,0 +1,18 @@
+# Generated by Django 3.2.25 on 2024-08-07 17:47
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('github', '0003_auto_20240528_0640'),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name='githubrepository',
+            name='tagging_enabled',
+            field=models.BooleanField(default=False),
+        ),
+    ]
diff --git a/api/integrations/github/models.py b/api/integrations/github/models.py
index 532e0760b9ff..546b009d601e 100644
--- a/api/integrations/github/models.py
+++ b/api/integrations/github/models.py
@@ -3,8 +3,14 @@
 
 from core.models import SoftDeleteExportableModel
 from django.db import models
-from django_lifecycle import BEFORE_DELETE, LifecycleModelMixin, hook
+from django_lifecycle import (
+    AFTER_CREATE,
+    BEFORE_DELETE,
+    LifecycleModelMixin,
+    hook,
+)
 
+from integrations.github.constants import GITHUB_TAG_COLOR
 from organisations.models import Organisation
 
 logger: logging.Logger = logging.getLogger(name=__name__)
@@ -48,6 +54,7 @@ class GithubRepository(LifecycleModelMixin, SoftDeleteExportableModel):
         null=False,
         on_delete=models.CASCADE,
     )
+    tagging_enabled = models.BooleanField(default=False)
 
     class Meta:
         constraints = [
@@ -84,3 +91,23 @@ def delete_feature_external_resources(
             # Filter by url containing the repository owner and name
             url__regex=pattern,
         ).delete()
+
+    @hook(AFTER_CREATE)
+    def create_github_tags(
+        self,
+    ) -> None:
+        from integrations.github.constants import (
+            GitHubTag,
+            github_tag_description,
+        )
+        from projects.tags.models import Tag, TagType
+
+        for tag_label in GitHubTag:
+            tag, created = Tag.objects.get_or_create(
+                color=GITHUB_TAG_COLOR,
+                description=github_tag_description[tag_label.value],
+                label=tag_label.value,
+                project=self.project,
+                is_system_tag=True,
+                type=TagType.GITHUB.value,
+            )
diff --git a/api/integrations/github/serializers.py b/api/integrations/github/serializers.py
index b3dc96c5263e..9d1cf3a81635 100644
--- a/api/integrations/github/serializers.py
+++ b/api/integrations/github/serializers.py
@@ -27,6 +27,7 @@ class Meta:
             "project",
             "repository_owner",
             "repository_name",
+            "tagging_enabled",
         )
         read_only_fields = (
             "id",
diff --git a/api/integrations/github/tasks.py b/api/integrations/github/tasks.py
index 8e94c9007b5d..970067daf0c4 100644
--- a/api/integrations/github/tasks.py
+++ b/api/integrations/github/tasks.py
@@ -6,8 +6,8 @@
 
 from features.models import Feature
 from integrations.github.client import post_comment_to_github
+from integrations.github.constants import GitHubEventType
 from integrations.github.dataclasses import CallGithubData
-from webhooks.webhooks import WebhookEventType
 
 logger = logging.getLogger(__name__)
 
@@ -29,8 +29,9 @@ def send_post_request(data: CallGithubData) -> None:
     )
 
     if (
-        event_type == WebhookEventType.FLAG_UPDATED.value
-        or event_type == WebhookEventType.FLAG_DELETED.value
+        event_type == GitHubEventType.FLAG_UPDATED.value
+        or event_type == GitHubEventType.FLAG_DELETED.value
+        or event_type == GitHubEventType.FLAG_UPDATED_FROM_GHA.value
     ):
         for resource in data.feature_external_resources:
             url = resource.get("url")
@@ -40,7 +41,7 @@ def send_post_request(data: CallGithubData) -> None:
                 installation_id, split_url[1], split_url[2], split_url[4], body
             )
 
-    elif event_type == WebhookEventType.FEATURE_EXTERNAL_RESOURCE_REMOVED.value:
+    elif event_type == GitHubEventType.FEATURE_EXTERNAL_RESOURCE_REMOVED.value:
         url = data.github_data.url
         pathname = urlparse(url).path
         split_url = pathname.split("/")
@@ -80,8 +81,8 @@ def generate_feature_external_resources(
         ]
 
     if (
-        github_event_data.type == WebhookEventType.FLAG_DELETED.value
-        or github_event_data.type == WebhookEventType.SEGMENT_OVERRIDE_DELETED.value
+        github_event_data.type == GitHubEventType.FLAG_DELETED.value
+        or github_event_data.type == GitHubEventType.SEGMENT_OVERRIDE_DELETED.value
     ):
         feature_external_resources = generate_feature_external_resources(
             list(
@@ -100,7 +101,7 @@ def generate_feature_external_resources(
 
     if (
         github_event_data.type
-        == WebhookEventType.FEATURE_EXTERNAL_RESOURCE_REMOVED.value
+        == GitHubEventType.FEATURE_EXTERNAL_RESOURCE_REMOVED.value
     ):
         data = CallGithubData(
             event_type=github_event_data.type,
diff --git a/api/integrations/github/views.py b/api/integrations/github/views.py
index 4cc2f3efea57..8d48a17dfa84 100644
--- a/api/integrations/github/views.py
+++ b/api/integrations/github/views.py
@@ -15,13 +15,17 @@
 
 from integrations.github.client import (
     ResourceType,
+    create_flagsmith_flag_label,
     delete_github_installation,
     fetch_github_repo_contributors,
     fetch_github_repositories,
     fetch_search_github_resource,
 )
 from integrations.github.exceptions import DuplicateGitHubIntegration
-from integrations.github.github import handle_github_webhook_event
+from integrations.github.github import (
+    handle_github_webhook_event,
+    tag_by_event_type,
+)
 from integrations.github.helpers import github_webhook_payload_is_valid
 from integrations.github.models import GithubConfiguration, GithubRepository
 from integrations.github.permissions import HasPermissionToGithubConfiguration
@@ -136,10 +140,20 @@ def get_queryset(self):
         except ValueError:
             raise ValidationError({"github_pk": ["Must be an integer"]})
 
-    def create(self, request, *args, **kwargs):
+    def create(self, request, *args, **kwargs) -> Response | None:
 
         try:
-            return super().create(request, *args, **kwargs)
+            response: Response = super().create(request, *args, **kwargs)
+            github_configuration: GithubConfiguration = GithubConfiguration.objects.get(
+                id=self.kwargs["github_pk"]
+            )
+            if request.data.get("tagging_enabled", False):
+                create_flagsmith_flag_label(
+                    installation_id=github_configuration.installation_id,
+                    owner=request.data.get("repository_owner"),
+                    repo=request.data.get("repository_name"),
+                )
+            return response
 
         except IntegrityError as e:
             if re.search(
@@ -150,6 +164,19 @@ def create(self, request, *args, **kwargs):
                     detail="Duplication error. The GitHub repository already linked"
                 )
 
+    def update(self, request, *args, **kwargs) -> Response | None:
+        response: Response = super().update(request, *args, **kwargs)
+        github_configuration: GithubConfiguration = GithubConfiguration.objects.get(
+            id=self.kwargs["github_pk"]
+        )
+        if request.data.get("tagging_enabled", False):
+            create_flagsmith_flag_label(
+                installation_id=github_configuration.installation_id,
+                owner=request.data.get("repository_owner"),
+                repo=request.data.get("repository_name"),
+            )
+        return response
+
 
 @api_view(["GET"])
 @permission_classes([IsAuthenticated, HasPermissionToGithubConfiguration])
@@ -250,7 +277,7 @@ def github_webhook(request) -> Response:
         payload_body=payload, secret_token=secret, signature_header=signature
     ):
         data = json.loads(payload.decode("utf-8"))
-        if github_event == "installation":
+        if github_event == "installation" or github_event in tag_by_event_type:
             handle_github_webhook_event(event_type=github_event, payload=data)
             return Response({"detail": "Event processed"}, status=200)
         else:
diff --git a/api/projects/tags/migrations/0006_alter_tag_type.py b/api/projects/tags/migrations/0006_alter_tag_type.py
new file mode 100644
index 000000000000..84736c31bd3f
--- /dev/null
+++ b/api/projects/tags/migrations/0006_alter_tag_type.py
@@ -0,0 +1,18 @@
+# Generated by Django 3.2.25 on 2024-05-27 15:03
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        ('tags', '0005_add_tag_fields_for_stale_flags_logic'),
+    ]
+
+    operations = [
+        migrations.AlterField(
+            model_name='tag',
+            name='type',
+            field=models.CharField(choices=[('NONE', 'None'), ('STALE', 'Stale'), ('GITHUB', 'Github')], default='NONE', help_text='Field used to provide a consistent identifier for the FE and API to use for business logic.', max_length=100),
+        ),
+    ]
diff --git a/api/projects/tags/models.py b/api/projects/tags/models.py
index 597bebdd0d9a..35c75eecfb7e 100644
--- a/api/projects/tags/models.py
+++ b/api/projects/tags/models.py
@@ -7,6 +7,7 @@
 class TagType(models.Choices):
     NONE = "NONE"
     STALE = "STALE"
+    GITHUB = "GITHUB"
 
 
 class Tag(AbstractBaseExportableModel):
diff --git a/api/tests/unit/features/test_unit_feature_external_resources_views.py b/api/tests/unit/features/test_unit_feature_external_resources_views.py
index 901454b6add6..d69b05766c0e 100644
--- a/api/tests/unit/features/test_unit_feature_external_resources_views.py
+++ b/api/tests/unit/features/test_unit_feature_external_resources_views.py
@@ -75,17 +75,15 @@ def test_create_feature_external_resource(
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
     post_request_mock: MagicMock,
-    mocker: MockerFixture,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
     # Given
-    mocker.patch(
-        "integrations.github.client.generate_token",
-        return_value="mocked_token",
+    repository_owner_name = (
+        f"{github_repository.repository_owner}/{github_repository.repository_name}"
     )
-
     feature_external_resource_data = {
         "type": "GITHUB_ISSUE",
-        "url": "https://github.com/repoowner/repo-name/issues/35",
+        "url": f"https://github.com/{repository_owner_name}/issues/35",
         "feature": feature_with_value.id,
         "metadata": {"state": "open"},
     }
@@ -130,7 +128,7 @@ def test_create_feature_external_resource(
         )
     )
     post_request_mock.assert_called_with(
-        "https://api.github.com/repos/repoowner/repo-name/issues/35/comments",
+        f"https://api.github.com/repos/{repository_owner_name}/issues/35/comments",
         json={"body": f"{expected_comment_body}"},
         headers={
             "Accept": "application/vnd.github.v3+json",
@@ -157,7 +155,7 @@ def test_create_feature_external_resource(
     # And When
     responses.add(
         method="GET",
-        url=f"{GITHUB_API_URL}repos/repoowner/repo-name/issues/35",
+        url=f"{GITHUB_API_URL}repos/{repository_owner_name}/issues/35",
         status=200,
         json={"title": "resource name", "state": "open"},
     )
@@ -183,6 +181,66 @@ def test_create_feature_external_resource(
     )
 
 
+def test_cannot_create_feature_external_resource_with_an_invalid_gh_url(
+    admin_client_new: APIClient,
+    feature: Feature,
+    project: Project,
+    github_configuration: GithubConfiguration,
+    github_repository: GithubRepository,
+) -> None:
+    # Given
+    feature_external_resource_data = {
+        "type": "GITHUB_ISSUE",
+        "url": "https://github.com/repoowner/repo-name/pull/1",
+        "feature": feature.id,
+        "metadata": {"state": "open"},
+    }
+
+    url = reverse(
+        "api-v1:projects:feature-external-resources-list",
+        kwargs={"project_pk": project.id, "feature_pk": feature.id},
+    )
+
+    # When
+    response = admin_client_new.post(
+        url, data=feature_external_resource_data, format="json"
+    )
+
+    # Then
+    assert response.status_code == status.HTTP_400_BAD_REQUEST
+    assert response.json()["detail"] == "Invalid GitHub Issue/PR URL"
+
+
+def test_cannot_create_feature_external_resource_with_an_incorrect_gh_type(
+    admin_client_new: APIClient,
+    feature: Feature,
+    project: Project,
+    github_configuration: GithubConfiguration,
+    github_repository: GithubRepository,
+) -> None:
+    # Given
+    feature_external_resource_data = {
+        "type": "GITHUB_INCORRECT_TYPE",
+        "url": "https://github.com/repoowner/repo-name/pull/1",
+        "feature": feature.id,
+        "metadata": {"state": "open"},
+    }
+
+    url = reverse(
+        "api-v1:projects:feature-external-resources-list",
+        kwargs={"project_pk": project.id, "feature_pk": feature.id},
+    )
+
+    # When
+    response = admin_client_new.post(
+        url, data=feature_external_resource_data, format="json"
+    )
+
+    # Then
+    assert response.status_code == status.HTTP_400_BAD_REQUEST
+    assert response.json()["detail"] == "Incorrect GitHub type"
+
+
 def test_cannot_create_feature_external_resource_when_doesnt_have_a_valid_github_integration(
     admin_client_new: APIClient,
     feature: Feature,
@@ -297,11 +355,11 @@ def test_update_feature_external_resource(
         "integrations.github.client.generate_token",
     )
     mock_generate_token.return_value = "mocked_token"
-    mock_generate_token.return_value = "mocked_token"
     feature_external_resource_data = {
         "type": "GITHUB_ISSUE",
         "url": "https://github.com/userexample/example-project-repo/issues/12",
         "feature": feature.id,
+        "metadata": '{"state": "open"}',
     }
     url = reverse(
         "api-v1:projects:feature-external-resources-detail",
@@ -338,7 +396,7 @@ def test_delete_feature_external_resource(
     post_request_mock.assert_called_with(
         "https://api.github.com/repos/repositoryownertest/repositorynametest/issues/11/comments",
         json={
-            "body": "### The feature flag `Test Feature1` was unlinked from the issue/PR"
+            "body": "**The feature flag `Test Feature1` was unlinked from the issue/PR**"
         },
         headers={
             "Accept": "application/vnd.github.v3+json",
@@ -361,12 +419,9 @@ def test_get_feature_external_resources(
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
     feature_external_resource: FeatureExternalResource,
-    mocker: MockerFixture,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
     # Given
-    mocker.patch(
-        "integrations.github.client.generate_token",
-    )
     url = reverse(
         "api-v1:projects:feature-external-resources-list",
         kwargs={"project_pk": project.id, "feature_pk": feature.id},
@@ -446,7 +501,7 @@ def test_create_github_comment_on_feature_state_updated(
     ).updated_at.strftime(get_format("DATETIME_INPUT_FORMATS")[0])
 
     expected_body_comment = (
-        "Flagsmith Feature `Test Feature1` has been updated:\n"
+        "**Flagsmith Feature `Test Feature1` has been updated:**\n"
         + expected_default_body(
             project.id,
             environment.api_key,
@@ -480,14 +535,9 @@ def test_create_github_comment_on_feature_was_deleted(
     github_repository: GithubRepository,
     feature_external_resource: FeatureExternalResource,
     post_request_mock: MagicMock,
-    mocker: MockerFixture,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
     # Given
-    mocker.patch(
-        "integrations.github.client.generate_token",
-        return_value="mocked_token",
-    )
-
     url = reverse(
         viewname="api-v1:projects:project-features-detail",
         kwargs={"project_pk": project.id, "pk": feature.id},
@@ -501,7 +551,7 @@ def test_create_github_comment_on_feature_was_deleted(
 
     post_request_mock.assert_called_with(
         "https://api.github.com/repos/repositoryownertest/repositorynametest/issues/11/comments",
-        json={"body": "### The Feature Flag `Test Feature1` was deleted"},
+        json={"body": "**The Feature Flag `Test Feature1` was deleted**"},
         headers={
             "Accept": "application/vnd.github.v3+json",
             "X-GitHub-Api-Version": GITHUB_API_VERSION,
@@ -518,18 +568,13 @@ def test_create_github_comment_on_segment_override_updated(
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
     post_request_mock: MagicMock,
-    mocker: MockerFixture,
     environment: Environment,
     admin_client: APIClient,
     feature_with_value_external_resource: FeatureExternalResource,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
     # Given
     feature_state = segment_override_for_feature_with_value
-    mocker.patch(
-        "integrations.github.client.generate_token",
-        return_value="mocked_token",
-    )
-
     payload = dict(WritableNestedFeatureStateSerializer(instance=feature_state).data)
 
     payload["enabled"] = not feature_state.enabled
@@ -549,7 +594,7 @@ def test_create_github_comment_on_segment_override_updated(
     ).updated_at.strftime(get_format("DATETIME_INPUT_FORMATS")[0])
 
     expected_comment_body = (
-        "Flagsmith Feature `feature_with_value` has been updated:\n"
+        "**Flagsmith Feature `feature_with_value` has been updated:**\n"
         + "\n"
         + expected_segment_comment_body(
             project.id,
@@ -581,16 +626,11 @@ def test_create_github_comment_on_segment_override_deleted(
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
     post_request_mock: MagicMock,
-    mocker: MockerFixture,
     admin_client_new: APIClient,
     feature_with_value_external_resource: FeatureExternalResource,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
     # Given
-    mocker.patch(
-        "integrations.github.client.generate_token",
-        return_value="mocked_token",
-    )
-
     url = reverse(
         viewname="api-v1:features:feature-segment-detail",
         kwargs={"pk": feature_with_value_segment.id},
@@ -606,7 +646,7 @@ def test_create_github_comment_on_segment_override_deleted(
     post_request_mock.assert_called_with(
         "https://api.github.com/repos/repositoryownertest/repositorynametest/issues/11/comments",
         json={
-            "body": "### The Segment Override `segment` for Feature Flag `feature_with_value` was deleted"
+            "body": "**The Segment Override `segment` for Feature Flag `feature_with_value` was deleted**"
         },
         headers={
             "Accept": "application/vnd.github.v3+json",
@@ -664,7 +704,7 @@ def test_create_github_comment_using_v2(
         response_data["updated_at"], format
     ).strftime(get_format("DATETIME_INPUT_FORMATS")[0])
     expected_comment_body = (
-        "Flagsmith Feature `Test Feature1` has been updated:\n"
+        "**Flagsmith Feature `Test Feature1` has been updated:**\n"
         + "\n"
         + expected_segment_comment_body(
             project.id,
@@ -745,19 +785,17 @@ def test_create_feature_external_resource_on_environment_with_v2(
     segment_override_for_feature_with_value: FeatureState,
     environment_v2_versioning: Environment,
     post_request_mock: MagicMock,
-    mocker: MockerFixture,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
     # Given
     feature_id = segment_override_for_feature_with_value.feature_id
-
-    mocker.patch(
-        "integrations.github.client.generate_token",
-        return_value="mocked_token",
+    repository_owner_name = (
+        f"{github_repository.repository_owner}/{github_repository.repository_name}"
     )
 
     feature_external_resource_data = {
         "type": "GITHUB_ISSUE",
-        "url": "https://github.com/repoowner/repo-name/issues/35",
+        "url": f"https://github.com/{repository_owner_name}/issues/35",
         "feature": feature_id,
         "metadata": {"state": "open"},
     }
@@ -804,7 +842,7 @@ def test_create_feature_external_resource_on_environment_with_v2(
     assert response.status_code == status.HTTP_201_CREATED
 
     post_request_mock.assert_called_with(
-        "https://api.github.com/repos/repoowner/repo-name/issues/35/comments",
+        f"https://api.github.com/repos/{repository_owner_name}/issues/35/comments",
         json={"body": f"{expected_comment_body}"},
         headers={
             "Accept": "application/vnd.github.v3+json",
@@ -813,3 +851,37 @@ def test_create_feature_external_resource_on_environment_with_v2(
         },
         timeout=10,
     )
+
+
+def test_cannot_create_feature_external_resource_for_the_same_feature_and_resource_uri(
+    admin_client_new: APIClient,
+    feature: Feature,
+    project: Project,
+    github_configuration: GithubConfiguration,
+    github_repository: GithubRepository,
+    feature_external_resource_gh_pr: FeatureExternalResource,
+) -> None:
+    # Given
+    feature_external_resource_data = {
+        "type": "GITHUB_PR",
+        "url": "https://github.com/repositoryownertest/repositorynametest/pull/1",
+        "feature": feature.id,
+        "metadata": {"state": "open"},
+    }
+
+    url = reverse(
+        "api-v1:projects:feature-external-resources-list",
+        kwargs={"project_pk": project.id, "feature_pk": feature.id},
+    )
+
+    # When
+    response = admin_client_new.post(
+        url, data=feature_external_resource_data, format="json"
+    )
+
+    # Then
+    assert response.status_code == status.HTTP_400_BAD_REQUEST
+    assert (
+        response.json()["non_field_errors"][0]
+        == "The fields feature, url must make a unique set."
+    )
diff --git a/api/tests/unit/integrations/github/test_unit_github_views.py b/api/tests/unit/integrations/github/test_unit_github_views.py
index 07d3e9660f14..a1d9add23f36 100644
--- a/api/tests/unit/integrations/github/test_unit_github_views.py
+++ b/api/tests/unit/integrations/github/test_unit_github_views.py
@@ -1,10 +1,10 @@
 import json
 from typing import Any
+from unittest.mock import MagicMock
 
 import pytest
 import requests
 import responses
-from django.conf import settings
 from django.urls import reverse
 from pytest_lazyfixture import lazy_fixture
 from pytest_mock import MockerFixture
@@ -12,7 +12,9 @@
 from rest_framework.response import Response
 from rest_framework.test import APIClient
 
+from environments.models import Environment
 from features.feature_external_resources.models import FeatureExternalResource
+from features.models import Feature
 from integrations.github.constants import GITHUB_API_URL
 from integrations.github.models import GithubConfiguration, GithubRepository
 from integrations.github.views import (
@@ -29,6 +31,17 @@
 WEBHOOK_PAYLOAD_WITHOUT_INSTALLATION_ID = json.dumps(
     {"installation": {"test": 765432}, "action": "deleted"}
 )
+WEBHOOK_PAYLOAD_MERGED = json.dumps(
+    {
+        "pull_request": {
+            "id": 1234567,
+            "html_url": "https://github.com/repositoryownertest/repositorynametest/issues/11",
+            "merged": True,
+        },
+        "action": "closed",
+    }
+)
+
 WEBHOOK_SIGNATURE = "sha1=57a1426e19cdab55dd6d0c191743e2958e50ccaa"
 WEBHOOK_SIGNATURE_WITH_AN_INVALID_INSTALLATION_ID = (
     "sha1=081eef49d04df27552587d5df1c6b76e0fe20d21"
@@ -36,6 +49,7 @@
 WEBHOOK_SIGNATURE_WITHOUT_INSTALLATION_ID = (
     "sha1=f99796bd3cebb902864e87ed960c5cca8772ff67"
 )
+WEBHOOK_MERGED_ACTION_SIGNATURE = "sha1=712ec7a5db14aad99d900da40738ebb9508ecad2"
 WEBHOOK_SECRET = "secret-key"
 
 
@@ -246,11 +260,14 @@ def test_cannot_get_github_repository_when_github_pk_in_not_a_number(
     assert response.json() == {"github_pk": ["Must be an integer"]}
 
 
+@responses.activate
 def test_create_github_repository(
     admin_client_new: APIClient,
     organisation: Organisation,
     github_configuration: GithubConfiguration,
     project: Project,
+    mocker: MockerFixture,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
     # Given
     data = {
@@ -258,8 +275,16 @@ def test_create_github_repository(
         "repository_owner": "repositoryowner",
         "repository_name": "repositoryname",
         "project": project.id,
+        "tagging_enabled": True,
     }
 
+    responses.add(
+        method="POST",
+        url=f"{GITHUB_API_URL}repos/repositoryowner/repositoryname/labels",
+        status=status.HTTP_200_OK,
+        json={},
+    )
+
     url = reverse(
         "api-v1:organisations:repositories-list",
         args=[organisation.id, github_configuration.id],
@@ -272,6 +297,53 @@ def test_create_github_repository(
     assert GithubRepository.objects.filter(repository_owner="repositoryowner").exists()
 
 
+@responses.activate
+def test_create_github_repository_and_label_already_Existe(
+    admin_client_new: APIClient,
+    organisation: Organisation,
+    github_configuration: GithubConfiguration,
+    project: Project,
+    mocker: MockerFixture,
+    mock_github_client_generate_token: MagicMock,
+) -> None:
+    # Given
+    mocker_logger = mocker.patch("integrations.github.client.logger")
+
+    data = {
+        "github_configuration": github_configuration.id,
+        "repository_owner": "repositoryowner",
+        "repository_name": "repositoryname",
+        "project": project.id,
+        "tagging_enabled": True,
+    }
+
+    mock_response = {
+        "message": "Validation Failed",
+        "errors": [{"resource": "Label", "code": "already_exists", "field": "name"}],
+        "documentation_url": "https://docs.github.com/rest/issues/labels#create-a-label",
+        "status": "422",
+    }
+
+    responses.add(
+        method="POST",
+        url=f"{GITHUB_API_URL}repos/repositoryowner/repositoryname/labels",
+        status=status.HTTP_422_UNPROCESSABLE_ENTITY,
+        json=mock_response,
+    )
+
+    url = reverse(
+        "api-v1:organisations:repositories-list",
+        args=[organisation.id, github_configuration.id],
+    )
+    # When
+    response = admin_client_new.post(url, data)
+
+    # Then
+    mocker_logger.warning.assert_called_once_with("Label already exists")
+    assert response.status_code == status.HTTP_201_CREATED
+    assert GithubRepository.objects.filter(repository_owner="repositoryowner").exists()
+
+
 def test_cannot_create_github_repository_when_does_not_have_permissions(
     test_user_client: APIClient,
     organisation: Organisation,
@@ -334,13 +406,9 @@ def test_github_delete_repository(
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
     feature_external_resource: FeatureExternalResource,
-    mocker: MockerFixture,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
     # Given
-    mock_generate_token = mocker.patch(
-        "integrations.github.client.generate_token",
-    )
-    mock_generate_token.return_value = "mocked_token"
     url = reverse(
         "api-v1:organisations:repositories-detail",
         args=[organisation.id, github_configuration.id, github_repository.id],
@@ -409,14 +477,10 @@ def test_fetch_pull_requests(
     organisation: Organisation,
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
+    mock_github_client_generate_token: MagicMock,
     mocker: MockerFixture,
 ) -> None:
-
     # Given
-    mock_generate_token = mocker.patch(
-        "integrations.github.client.generate_token",
-    )
-    mock_generate_token.return_value = "mocked_token"
     github_request_mock = mocker.patch(
         "requests.get", side_effect=mocked_requests_get_issues_and_pull_requests
     )
@@ -448,13 +512,10 @@ def test_fetch_issues(
     organisation: Organisation,
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
+    mock_github_client_generate_token: MagicMock,
     mocker: MockerFixture,
 ) -> None:
     # Given
-    mock_generate_token = mocker.patch(
-        "integrations.github.client.generate_token",
-    )
-    mock_generate_token.return_value = "mocked_token"
     github_request_mock = mocker.patch(
         "requests.get", side_effect=mocked_requests_get_issues_and_pull_requests
     )
@@ -491,13 +552,10 @@ def test_fetch_issues_returns_error_on_bad_response_from_github(
     organisation: Organisation,
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
+    mock_github_client_generate_token: MagicMock,
     mocker: MockerFixture,
 ) -> None:
     # Given
-    mock_generate_token = mocker.patch(
-        "integrations.github.client.generate_token",
-    )
-    mock_generate_token.return_value = "mocked_token"
     mocker.patch("requests.get", side_effect=mocked_requests_get_error)
     url = reverse("api-v1:organisations:get-github-issues", args=[organisation.id])
     data = {"repo_owner": "owner", "repo_name": "repo"}
@@ -519,13 +577,9 @@ def test_fetch_repositories(
     organisation: Organisation,
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
-    mocker: MockerFixture,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
     # Given
-    mock_generate_token = mocker.patch(
-        "integrations.github.client.generate_token",
-    )
-    mock_generate_token.return_value = "mocked_token"
     responses.add(
         method="GET",
         url=f"{GITHUB_API_URL}installation/repositories",
@@ -573,13 +627,11 @@ def test_fetch_repositories(
     ],
 )
 def test_fetch_issues_and_pull_requests_fails_with_status_400_when_integration_not_configured(
-    client: APIClient, organisation: Organisation, reverse_url: str, mocker
+    client: APIClient,
+    organisation: Organisation,
+    reverse_url: str,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
-    # Given
-    mock_generate_token = mocker.patch(
-        "integrations.github.client.generate_token",
-    )
-    mock_generate_token.generate_token.return_value = "mocked_token"
     # When
     url = reverse(reverse_url, args=[organisation.id])
     response = client.get(url)
@@ -600,15 +652,9 @@ def test_cannot_fetch_issues_or_prs_when_does_not_have_permissions(
     organisation: Organisation,
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
-    mocker,
+    mock_github_client_generate_token: MagicMock,
     reverse_url: str,
 ) -> None:
-    # Given
-    mock_generate_token = mocker.patch(
-        "integrations.github.client.generate_token",
-    )
-    mock_generate_token.generate_token.return_value = "mocked_token"
-
     # When
     url = reverse(reverse_url, args=[organisation.id])
     response = test_user_client.get(url)
@@ -656,9 +702,9 @@ def test_verify_github_webhook_payload_returns_false_on_no_signature_header() ->
 def test_github_webhook_delete_installation(
     api_client: APIClient,
     github_configuration: GithubConfiguration,
+    set_github_webhook_secret,
 ) -> None:
     # Given
-    settings.GITHUB_WEBHOOK_SECRET = WEBHOOK_SECRET
     url = reverse("api-v1:github-webhook")
 
     # When
@@ -675,63 +721,88 @@ def test_github_webhook_delete_installation(
     assert not GithubConfiguration.objects.filter(installation_id=1234567).exists()
 
 
-def test_github_webhook_with_non_existing_installation(
+def test_github_webhook_merged_a_pull_request(
     api_client: APIClient,
+    feature: Feature,
     github_configuration: GithubConfiguration,
+    github_repository: GithubRepository,
+    feature_external_resource: FeatureExternalResource,
+    set_github_webhook_secret,
+) -> None:
+    # Given
+    url = reverse("api-v1:github-webhook")
+
+    # When
+    response = api_client.post(
+        path=url,
+        data=WEBHOOK_PAYLOAD_MERGED,
+        content_type="application/json",
+        HTTP_X_HUB_SIGNATURE=WEBHOOK_MERGED_ACTION_SIGNATURE,
+        HTTP_X_GITHUB_EVENT="pull_request",
+    )
+
+    # Then
+    feature.refresh_from_db()
+    assert response.status_code == status.HTTP_200_OK
+    assert feature.tags.first().label == "PR Merged"
+
+
+def test_github_webhook_without_installation_id(
+    api_client: APIClient,
     mocker: MockerFixture,
+    set_github_webhook_secret,
 ) -> None:
     # Given
-    settings.GITHUB_WEBHOOK_SECRET = WEBHOOK_SECRET
     url = reverse("api-v1:github-webhook")
     mocker_logger = mocker.patch("integrations.github.github.logger")
 
     # When
     response = api_client.post(
         path=url,
-        data=WEBHOOK_PAYLOAD_WITH_AN_INVALID_INSTALLATION_ID,
+        data=WEBHOOK_PAYLOAD_WITHOUT_INSTALLATION_ID,
         content_type="application/json",
-        HTTP_X_HUB_SIGNATURE=WEBHOOK_SIGNATURE_WITH_AN_INVALID_INSTALLATION_ID,
+        HTTP_X_HUB_SIGNATURE=WEBHOOK_SIGNATURE_WITHOUT_INSTALLATION_ID,
         HTTP_X_GITHUB_EVENT="installation",
     )
 
     # Then
     mocker_logger.error.assert_called_once_with(
-        "GitHub Configuration with installation_id 765432 does not exist"
+        "The installation_id is not present in the payload: {'installation': {'test': 765432}, 'action': 'deleted'}"
     )
     assert response.status_code == status.HTTP_200_OK
 
 
-def test_github_webhook_without_installation_id(
+def test_github_webhook_with_non_existing_installation(
     api_client: APIClient,
     github_configuration: GithubConfiguration,
     mocker: MockerFixture,
+    set_github_webhook_secret,
 ) -> None:
     # Given
-    settings.GITHUB_WEBHOOK_SECRET = WEBHOOK_SECRET
     url = reverse("api-v1:github-webhook")
     mocker_logger = mocker.patch("integrations.github.github.logger")
 
     # When
     response = api_client.post(
         path=url,
-        data=WEBHOOK_PAYLOAD_WITHOUT_INSTALLATION_ID,
+        data=WEBHOOK_PAYLOAD_WITH_AN_INVALID_INSTALLATION_ID,
         content_type="application/json",
-        HTTP_X_HUB_SIGNATURE=WEBHOOK_SIGNATURE_WITHOUT_INSTALLATION_ID,
+        HTTP_X_HUB_SIGNATURE=WEBHOOK_SIGNATURE_WITH_AN_INVALID_INSTALLATION_ID,
         HTTP_X_GITHUB_EVENT="installation",
     )
 
     # Then
     mocker_logger.error.assert_called_once_with(
-        "The installation_id is not present in the payload: {'installation': {'test': 765432}, 'action': 'deleted'}"
+        "GitHub Configuration with installation_id 765432 does not exist"
     )
     assert response.status_code == status.HTTP_200_OK
 
 
 def test_github_webhook_fails_on_signature_header_missing(
     github_configuration: GithubConfiguration,
+    set_github_webhook_secret,
 ) -> None:
     # Given
-    settings.GITHUB_WEBHOOK_SECRET = WEBHOOK_SECRET
     url = reverse("api-v1:github-webhook")
 
     # When
@@ -751,9 +822,9 @@ def test_github_webhook_fails_on_signature_header_missing(
 
 def test_github_webhook_fails_on_bad_signature_header_missing(
     github_configuration: GithubConfiguration,
+    set_github_webhook_secret,
 ) -> None:
     # Given
-    settings.GITHUB_WEBHOOK_SECRET = WEBHOOK_SECRET
     url = reverse("api-v1:github-webhook")
 
     # When
@@ -774,9 +845,9 @@ def test_github_webhook_fails_on_bad_signature_header_missing(
 
 def test_github_webhook_bypass_event(
     github_configuration: GithubConfiguration,
+    set_github_webhook_secret,
 ) -> None:
     # Given
-    settings.GITHUB_WEBHOOK_SECRET = WEBHOOK_SECRET
     url = reverse("api-v1:github-webhook")
 
     # When
@@ -800,15 +871,10 @@ def test_cannot_fetch_pull_requests_when_github_request_call_failed(
     organisation: Organisation,
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
-    mocker,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
-
     # Given
     data = {"repo_owner": "owner", "repo_name": "repo"}
-    mock_generate_token = mocker.patch(
-        "integrations.github.client.generate_token",
-    )
-    mock_generate_token.return_value = "mocked_token"
     responses.add(
         method="GET",
         url=f"{GITHUB_API_URL}repos/{data['repo_owner']}/{data['repo_name']}/pulls",
@@ -833,14 +899,10 @@ def test_cannot_fetch_pulls_when_the_github_response_was_invalid(
     organisation: Organisation,
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
-    mocker,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
     # Given
     data = {"repo_owner": "owner", "repo_name": "repo"}
-    mock_generate_token = mocker.patch(
-        "integrations.github.client.generate_token",
-    )
-    mock_generate_token.return_value = "mocked_token"
     responses.add(
         method="GET",
         url=f"{GITHUB_API_URL}repos/{data['repo_owner']}/{data['repo_name']}/pulls",
@@ -877,7 +939,7 @@ def test_fetch_github_repo_contributors(
     organisation: Organisation,
     github_configuration: GithubConfiguration,
     github_repository: GithubRepository,
-    mocker: MockerFixture,
+    mock_github_client_generate_token: MagicMock,
 ) -> None:
     # Given
     url = reverse(
@@ -905,11 +967,6 @@ def test_fetch_github_repo_contributors(
 
     expected_response = {"results": mocked_github_response}
 
-    mock_generate_token = mocker.patch(
-        "integrations.github.client.generate_token",
-    )
-    mock_generate_token.return_value = "mocked_token"
-
     # Add response for endpoint being tested
     responses.add(
         method=responses.GET,
@@ -1063,3 +1120,85 @@ def test_send_the_invalid_type_page_or_page_size_param_returns_400(
     assert response.status_code == status.HTTP_400_BAD_REQUEST
     response_json = response.json()
     assert response_json == error_response
+
+
+@responses.activate
+def test_label_and_tags_no_added_when_tagging_is_disabled(
+    admin_client_new: APIClient,
+    project: Project,
+    environment: Environment,
+    github_repository: GithubRepository,
+    feature_with_value: Feature,
+    mock_github_client_generate_token: MagicMock,
+    post_request_mock: MagicMock,
+) -> None:
+    # Given
+    github_repository.tagging_enabled = False
+    github_repository.save()
+    repository_owner_name = (
+        f"{github_repository.repository_owner}/{github_repository.repository_name}"
+    )
+
+    feature_external_resource_data = {
+        "type": "GITHUB_ISSUE",
+        "url": f"https://github.com/{repository_owner_name}/issues/35",
+        "feature": feature_with_value.id,
+        "metadata": {"state": "open"},
+    }
+
+    url = reverse(
+        "api-v1:projects:feature-external-resources-list",
+        kwargs={"project_pk": project.id, "feature_pk": feature_with_value.id},
+    )
+
+    # When
+    response = admin_client_new.post(
+        url, data=feature_external_resource_data, format="json"
+    )
+
+    # Then
+    assert response.status_code == status.HTTP_201_CREATED
+    assert feature_with_value.tags.count() == 0
+
+
+@responses.activate
+def test_update_github_repository(
+    admin_client_new: APIClient,
+    organisation: Organisation,
+    github_configuration: GithubConfiguration,
+    github_repository: GithubRepository,
+    project: Project,
+    mocker: MockerFixture,
+    mock_github_client_generate_token: MagicMock,
+) -> None:
+    # Given
+    github_repository.tagging_enabled = False
+    github_repository.save()
+    data = {
+        "github_configuration": github_configuration.id,
+        "repository_owner": "repositoryowner",
+        "repository_name": "repositoryname",
+        "project": project.id,
+        "tagging_enabled": True,
+    }
+
+    responses.add(
+        method="POST",
+        url=f"{GITHUB_API_URL}repos/repositoryowner/repositoryname/labels",
+        status=status.HTTP_200_OK,
+        json={},
+    )
+
+    url = reverse(
+        "api-v1:organisations:repositories-detail",
+        args=[organisation.id, github_configuration.id, github_repository.id],
+    )
+    # When
+    response = admin_client_new.put(url, data)
+
+    # Then
+    assert response.status_code == status.HTTP_200_OK
+    assert GithubRepository.objects.filter(repository_owner="repositoryowner").exists()
+    assert GithubRepository.objects.get(
+        repository_owner="repositoryowner"
+    ).tagging_enabled
diff --git a/api/webhooks/webhooks.py b/api/webhooks/webhooks.py
index 75684e886614..e314b5976f9f 100644
--- a/api/webhooks/webhooks.py
+++ b/api/webhooks/webhooks.py
@@ -39,9 +39,6 @@ class WebhookEventType(enum.Enum):
     FLAG_DELETED = "FLAG_DELETED"
     AUDIT_LOG_CREATED = "AUDIT_LOG_CREATED"
     NEW_VERSION_PUBLISHED = "NEW_VERSION_PUBLISHED"
-    FEATURE_EXTERNAL_RESOURCE_ADDED = "FEATURE_EXTERNAL_RESOURCE_ADDED"
-    FEATURE_EXTERNAL_RESOURCE_REMOVED = "FEATURE_EXTERNAL_RESOURCE_REMOVED"
-    SEGMENT_OVERRIDE_DELETED = "SEGMENT_OVERRIDE_DELETED"
 
 
 class WebhookType(enum.Enum):