diff --git a/api/features/versioning/tasks.py b/api/features/versioning/tasks.py
index e44f99237ca5..57c8f2c3b932 100644
--- a/api/features/versioning/tasks.py
+++ b/api/features/versioning/tasks.py
@@ -36,7 +36,7 @@ def enable_v2_versioning(environment_id: int):
 
 
 def _create_initial_feature_versions(environment: "Environment"):
-    from features.models import Feature
+    from features.models import Feature, FeatureSegment
 
     now = timezone.now()
 
@@ -47,9 +47,16 @@ def _create_initial_feature_versions(environment: "Environment"):
             published_at=now,
             live_from=now,
         )
-        get_environment_flags_queryset(environment=environment).filter(
-            identity__isnull=True, feature=feature
-        ).update(environment_feature_version=ef_version)
+
+        latest_feature_states = get_environment_flags_queryset(
+            environment=environment
+        ).filter(identity__isnull=True, feature=feature)
+        related_feature_segments = FeatureSegment.objects.filter(
+            feature_states__in=latest_feature_states
+        )
+
+        latest_feature_states.update(environment_feature_version=ef_version)
+        related_feature_segments.update(environment_feature_version=ef_version)
 
 
 @register_task_handler()
diff --git a/api/tests/integration/features/versioning/test_integration_v2_versioning.py b/api/tests/integration/features/versioning/test_integration_v2_versioning.py
index 91c1f0f325de..c1f512f7e956 100644
--- a/api/tests/integration/features/versioning/test_integration_v2_versioning.py
+++ b/api/tests/integration/features/versioning/test_integration_v2_versioning.py
@@ -514,3 +514,62 @@ def test_v2_versioning_multiple_segment_overrides(
         second_create_environment_feature_version_response.status_code
         == status.HTTP_201_CREATED
     )
+
+
+def test_v2_versioning_carries_existing_segment_overrides_across(
+    environment: int,
+    environment_api_key: str,
+    admin_client: "APIClient",
+    segment: int,
+    feature: int,
+    feature_segment: int,
+    segment_featurestate: int,
+) -> None:
+    """
+    This is a specific test to reproduce an issue found in testing where, after
+    enabling v2 versioning, feature segments were not being returned via the
+    API.
+    """
+    # Given
+    feature_segments_list_url = "%s?feature=%d&environment=%d" % (
+        reverse("api-v1:features:feature-segment-list"),
+        feature,
+        environment,
+    )
+
+    # Firstly, let's check the response to the feature segments list endpoint
+    # before we enable v2 versioning.
+    feature_segment_list_pre_migrate_response = admin_client.get(
+        feature_segments_list_url
+    )
+    feature_segments_list_response_pre_migrate_json = (
+        feature_segment_list_pre_migrate_response.json()
+    )
+    assert feature_segments_list_response_pre_migrate_json["count"] == 1
+    assert (
+        feature_segments_list_response_pre_migrate_json["results"][0]["id"]
+        == feature_segment
+    )
+
+    # Now, let's enable v2 versioning.
+    enable_v2_versioning_url = reverse(
+        "api-v1:environments:environment-enable-v2-versioning",
+        args=[environment_api_key],
+    )
+    assert (
+        admin_client.post(enable_v2_versioning_url).status_code
+        == status.HTTP_202_ACCEPTED
+    )
+
+    # and let's check the response to the feature segments endpoint after enabling v2 versioning
+    feature_segment_list_post_migrate_response = admin_client.get(
+        feature_segments_list_url
+    )
+    feature_segment_list_post_migrate_response_json = (
+        feature_segment_list_post_migrate_response.json()
+    )
+    assert feature_segment_list_post_migrate_response_json["count"] == 1
+    assert (
+        feature_segment_list_post_migrate_response_json["results"][0]["id"]
+        == feature_segment
+    )