diff --git a/backend/internal/server/middleware/api_key_auth_google.go b/backend/internal/server/middleware/api_key_auth_google.go
index 3ed71f71..596bed52 100644
--- a/backend/internal/server/middleware/api_key_auth_google.go
+++ b/backend/internal/server/middleware/api_key_auth_google.go
@@ -55,6 +55,7 @@ func APIKeyAuthWithSubscriptionGoogle(apiKeyService *service.APIKeyService, subs
 			return
 		}
 		if _, message, ok := validateAPIKeyGroupAvailable(apiKey); !ok {
+			service.MarkOpsClientBusinessLimited(c, service.OpsClientBusinessLimitedReasonAPIKeyGroupUnavailable)
 			abortWithGoogleError(c, 403, message)
 			return
 		}
diff --git a/backend/internal/server/middleware/api_key_auth_google_test.go b/backend/internal/server/middleware/api_key_auth_google_test.go
index f8e50fcd..feadd27d 100644
--- a/backend/internal/server/middleware/api_key_auth_google_test.go
+++ b/backend/internal/server/middleware/api_key_auth_google_test.go
@@ -373,6 +373,68 @@ func TestApiKeyAuthWithSubscriptionGoogle_InvalidKey(t *testing.T) {
 	require.Equal(t, "UNAUTHENTICATED", resp.Error.Status)
 }
 
+func TestApiKeyAuthWithSubscriptionGoogle_MarksUnavailableGroupBusinessLimited(t *testing.T) {
+	gin.SetMode(gin.TestMode)
+
+	groupID := int64(101)
+	user := &service.User{
+		ID:          7,
+		Role:        service.RoleUser,
+		Status:      service.StatusActive,
+		Balance:     10,
+		Concurrency: 3,
+	}
+	apiKey := &service.APIKey{
+		ID:      100,
+		UserID:  user.ID,
+		GroupID: &groupID,
+		Key:     "google-group-deleted",
+		Status:  service.StatusActive,
+		User:    user,
+		Group: &service.Group{
+			ID:       groupID,
+			Name:     "deleted",
+			Status:   "deleted",
+			Platform: service.PlatformGemini,
+			Hydrated: true,
+		},
+	}
+
+	r := gin.New()
+	var markedBusinessLimited bool
+	var businessLimitedReason string
+	r.Use(func(c *gin.Context) {
+		c.Next()
+		markedBusinessLimited = service.HasOpsClientBusinessLimited(c)
+		if v, ok := c.Get(service.OpsClientBusinessLimitedReasonKey); ok {
+			businessLimitedReason, _ = v.(string)
+		}
+	})
+	apiKeyService := newTestAPIKeyService(fakeAPIKeyRepo{
+		getByKey: func(ctx context.Context, key string) (*service.APIKey, error) {
+			if key != apiKey.Key {
+				return nil, service.ErrAPIKeyNotFound
+			}
+			clone := *apiKey
+			return &clone, nil
+		},
+	})
+	r.Use(APIKeyAuthWithSubscriptionGoogle(apiKeyService, nil, &config.Config{RunMode: config.RunModeSimple}))
+	r.GET("/v1beta/test", func(c *gin.Context) { c.JSON(200, gin.H{"ok": true}) })
+
+	req := httptest.NewRequest(http.MethodGet, "/v1beta/test", nil)
+	req.Header.Set("x-goog-api-key", apiKey.Key)
+	rec := httptest.NewRecorder()
+	r.ServeHTTP(rec, req)
+
+	require.Equal(t, http.StatusForbidden, rec.Code)
+	var resp googleErrorResponse
+	require.NoError(t, json.Unmarshal(rec.Body.Bytes(), &resp))
+	require.Equal(t, "API Key 所属分组已删除", resp.Error.Message)
+	require.True(t, markedBusinessLimited)
+	require.Equal(t, service.OpsClientBusinessLimitedReasonAPIKeyGroupUnavailable, businessLimitedReason)
+}
+
 func TestApiKeyAuthWithSubscriptionGoogle_RepoError(t *testing.T) {
 	gin.SetMode(gin.TestMode)