diff --git a/src/sentry/integrations/github/webhook.py b/src/sentry/integrations/github/webhook.py
index 7bee3f156b98..e955794f2579 100644
--- a/src/sentry/integrations/github/webhook.py
+++ b/src/sentry/integrations/github/webhook.py
@@ -14,6 +14,7 @@
 from django.views.decorators.csrf import csrf_exempt
 from django.views.generic import View
 from rest_framework.request import Request
+from sentry_sdk import configure_scope
 
 from sentry import options
 from sentry.constants import ObjectStatus
@@ -30,12 +31,26 @@
 from sentry.shared_integrations.exceptions import ApiError
 from sentry.utils import json
 from sentry.utils.json import JSONData
+from sentry.utils.sdk import report_tags_already_set
 
 from .repository import GitHubRepositoryProvider
 
 logger = logging.getLogger("sentry.webhooks")
 
 
+def clear_tags_and_context_if_already_set() -> None:
+    with configure_scope() as scope:
+        report_tags_already_set(scope)
+        for tag in ["organization", "organization.slug"]:
+            if tag in scope._tags:
+                del scope._tags[tag]
+
+        if "organization" in scope._contexts:
+            del scope._contexts["organization"]
+
+        logger.info("We've reset the context and tags.")
+
+
 class Webhook:
     provider = "github"
 
@@ -456,6 +471,7 @@ def get_secret(self) -> str | None:
         raise NotImplementedError
 
     def handle(self, request: Request) -> HttpResponse:
+        clear_tags_and_context_if_already_set()
         secret = self.get_secret()
 
         if secret is None:
diff --git a/src/sentry/utils/sdk.py b/src/sentry/utils/sdk.py
index 8bd776fe7039..3dd229933904 100644
--- a/src/sentry/utils/sdk.py
+++ b/src/sentry/utils/sdk.py
@@ -1,5 +1,6 @@
 import copy
 import inspect
+import logging
 import random
 
 import sentry_sdk
@@ -8,7 +9,13 @@
 
 # Reexport sentry_sdk just in case we ever have to write another shim like we
 # did for raven
-from sentry_sdk import capture_exception, capture_message, configure_scope, push_scope  # NOQA
+from sentry_sdk import (  # NOQA
+    Scope,
+    capture_exception,
+    capture_message,
+    configure_scope,
+    push_scope,
+)
 from sentry_sdk.client import get_options
 from sentry_sdk.transport import make_transport
 from sentry_sdk.utils import logger as sdk_logger
@@ -18,6 +25,8 @@
 from sentry.utils.db import DjangoAtomicIntegration
 from sentry.utils.rust import RustInfoIntegration
 
+logger = logging.getLogger(__name__)
+
 UNSAFE_FILES = (
     "sentry/event_manager.py",
     "sentry/tasks/process_buffer.py",
@@ -445,11 +454,27 @@ def _kwargs_into_scope(self, scope, extra=None, tags=None, fingerprint=None, req
             scope.fingerprint = fingerprint
 
 
+# We have some events being tagged with organization.slug even when we don't have such info
+def report_tags_already_set(scope: Scope):
+    """If the tags are already set, report them as a Sentry error."""
+    try:
+
+        if scope._tags != {}:
+            for tag in ["organization", "organization.slug"]:
+                if tag in scope._tags:
+                    logger.info(f"Tags already set: {scope._tags}")
+                    raise Exception("Tags are already set. Code execution will not be affected.")
+    except Exception as e:
+        logger.exception(e)
+
+
 def bind_organization_context(organization):
     helper = settings.SENTRY_ORGANIZATION_CONTEXT_HELPER
 
     # XXX(dcramer): this is duplicated in organizationContext.jsx on the frontend
     with sentry_sdk.configure_scope() as scope:
+        report_tags_already_set(scope)
+
         scope.set_tag("organization", organization.id)
         scope.set_tag("organization.slug", organization.slug)
         scope.set_context("organization", {"id": organization.id, "slug": organization.slug})