diff --git a/api/integrations/gitlab/mappers.py b/api/integrations/gitlab/mappers.py
index 7846af55b487..1567e0f3ce08 100644
--- a/api/integrations/gitlab/mappers.py
+++ b/api/integrations/gitlab/mappers.py
@@ -56,6 +56,21 @@ def map_gitlab_resource_to_tag_label(
     return None
 
 
+def map_resource_url_to_filter_value(url: str) -> list[str]:
+    """Return a list of equivalent URL shapes for use as an ``__in`` filter
+    value when looking up a linked GitLab resource.
+
+    GitLab delivers issue webhooks with ``/-/work_items/<iid>`` URLs even when
+    the feature was linked via the legacy ``/-/issues/<iid>`` form, and vice
+    versa. Both shapes refer to the same issue.
+    """
+    if "/-/issues/" in url:
+        return [url, url.replace("/-/issues/", "/-/work_items/", 1)]
+    if "/-/work_items/" in url:
+        return [url, url.replace("/-/work_items/", "/-/issues/", 1)]
+    return [url]
+
+
 def map_gitlab_webhook_payload_to_tag_label(
     payload: GitLabWebhookPayload,
 ) -> GitLabTagLabel | None:
diff --git a/api/integrations/gitlab/services.py b/api/integrations/gitlab/services.py
index 76a51ea608c9..7e1d2353b3a6 100644
--- a/api/integrations/gitlab/services.py
+++ b/api/integrations/gitlab/services.py
@@ -27,6 +27,7 @@
 from integrations.gitlab.mappers import (
     map_gitlab_resource_to_tag_label,
     map_gitlab_webhook_payload_to_tag_label,
+    map_resource_url_to_filter_value,
 )
 from integrations.gitlab.models import GitLabConfiguration, GitLabWebhook
 from integrations.gitlab.types import GitLabWebhookPayload
@@ -215,7 +216,7 @@ def apply_tag_for_event(
     if not (
         feature := Feature.objects.filter(
             project=webhook.gitlab_configuration.project,
-            external_resources__url=resource_url,
+            external_resources__url__in=map_resource_url_to_filter_value(resource_url),
             external_resources__type__in=GITLAB_RESOURCE_TYPES,
         ).first()
     ):
diff --git a/api/tests/integration/features/test_gitlab_webhook.py b/api/tests/integration/features/test_gitlab_webhook.py
index 4bf29b55fceb..ff39417b21be 100644
--- a/api/tests/integration/features/test_gitlab_webhook.py
+++ b/api/tests/integration/features/test_gitlab_webhook.py
@@ -71,6 +71,50 @@ def _link(
     return _link
 
 
+@pytest.mark.parametrize(
+    "linked_url, payload_url",
+    [
+        (
+            "https://gitlab.example.com/testorg/testrepo/-/issues/42",
+            "https://gitlab.example.com/testorg/testrepo/-/work_items/42",
+        ),
+        (
+            "https://gitlab.example.com/testorg/testrepo/-/work_items/42",
+            "https://gitlab.example.com/testorg/testrepo/-/issues/42",
+        ),
+    ],
+)
+def test_gitlab_webhook__issue_url_variants__still_matches_feature(
+    api_client: APIClient,
+    feature: int,
+    webhook_url: str,
+    link_feature: LinkFeatureFixture,
+    linked_url: str,
+    payload_url: str,
+) -> None:
+    # Given — GitLab may deliver ``work_items`` URLs even when the link uses the
+    # legacy ``issues`` path (or vice versa). Both shapes refer to the same issue.
+    link_feature(linked_url, ResourceType.GITLAB_ISSUE, metadata={"state": "opened"})
+    payload = {
+        "object_kind": "issue",
+        "object_attributes": {"url": payload_url, "state": "closed"},
+    }
+
+    # When
+    response = api_client.post(
+        webhook_url,
+        data=payload,
+        format="json",
+        HTTP_X_GITLAB_TOKEN=WEBHOOK_SECRET,
+    )
+
+    # Then
+    assert response.status_code == status.HTTP_200_OK
+    labels = set(Feature.objects.get(id=feature).tags.values_list("label", flat=True))
+    assert GitLabTagLabel.ISSUE_CLOSED.value in labels
+    assert GitLabTagLabel.ISSUE_OPEN.value not in labels
+
+
 @pytest.mark.django_db()
 def test_gitlab_webhook__issue_close_event__switches_tag_to_issue_closed(
     api_client: APIClient,
diff --git a/docs/docs/deployment-self-hosting/observability/_events-catalogue.md b/docs/docs/deployment-self-hosting/observability/_events-catalogue.md
index 81eb31771b3e..3d827d1d4fb2 100644
--- a/docs/docs/deployment-self-hosting/observability/_events-catalogue.md
+++ b/docs/docs/deployment-self-hosting/observability/_events-catalogue.md
@@ -98,7 +98,7 @@ Attributes:
 ### `gitlab.feature.tagged`
 
 Logged at `info` from:
- - `api/integrations/gitlab/services.py:229`
+ - `api/integrations/gitlab/services.py:230`
 
 Attributes:
  - `action`
@@ -111,7 +111,7 @@ Attributes:
 ### `gitlab.webhook.deregistered`
 
 Logged at `info` from:
- - `api/integrations/gitlab/services.py:159`
+ - `api/integrations/gitlab/services.py:160`
 
 Attributes:
  - `gitlab.hook.id`
@@ -122,7 +122,7 @@ Attributes:
 ### `gitlab.webhook.deregistration_failed`
 
 Logged at `warning` from:
- - `api/integrations/gitlab/services.py:152`
+ - `api/integrations/gitlab/services.py:153`
 
 Attributes:
  - `exc_info`
@@ -134,7 +134,7 @@ Attributes:
 ### `gitlab.webhook.registered`
 
 Logged at `info` from:
- - `api/integrations/gitlab/services.py:112`
+ - `api/integrations/gitlab/services.py:113`
 
 Attributes:
  - `gitlab.hook.id`
@@ -146,7 +146,7 @@ Attributes:
 ### `gitlab.webhook.registration_failed`
 
 Logged at `error` from:
- - `api/integrations/gitlab/services.py:97`
+ - `api/integrations/gitlab/services.py:98`
 
 Attributes:
  - `exc_info`