diff --git a/backend/src/features/subscriptions/api/subscriptions.controller.ts b/backend/src/features/subscriptions/api/subscriptions.controller.ts
index 719eba3..36616c1 100644
--- a/backend/src/features/subscriptions/api/subscriptions.controller.ts
+++ b/backend/src/features/subscriptions/api/subscriptions.controller.ts
@@ -49,6 +49,28 @@ export class SubscriptionsController {
     }
   }
 
+  /**
+   * GET /api/subscriptions/needs-vehicle-selection - Check if user needs vehicle selection
+   */
+  async checkNeedsVehicleSelection(request: FastifyRequest, reply: FastifyReply): Promise<void> {
+    try {
+      const userId = (request as any).user.sub;
+
+      const result = await this.service.checkNeedsVehicleSelection(userId);
+
+      reply.status(200).send(result);
+    } catch (error: any) {
+      logger.error('Failed to check needs vehicle selection', {
+        userId: (request as any).user?.sub,
+        error: error.message,
+      });
+      reply.status(500).send({
+        error: 'Failed to check needs vehicle selection',
+        message: error.message,
+      });
+    }
+  }
+
   /**
    * POST /api/subscriptions/checkout - Create Stripe checkout session
    */
diff --git a/backend/src/features/subscriptions/api/subscriptions.routes.ts b/backend/src/features/subscriptions/api/subscriptions.routes.ts
index cca8439..7ef9595 100644
--- a/backend/src/features/subscriptions/api/subscriptions.routes.ts
+++ b/backend/src/features/subscriptions/api/subscriptions.routes.ts
@@ -19,6 +19,12 @@ export const subscriptionsRoutes: FastifyPluginAsync = async (
     handler: subscriptionsController.getSubscription.bind(subscriptionsController)
   });
 
+  // GET /api/subscriptions/needs-vehicle-selection - Check if user needs vehicle selection
+  fastify.get('/subscriptions/needs-vehicle-selection', {
+    preHandler: [fastify.authenticate],
+    handler: subscriptionsController.checkNeedsVehicleSelection.bind(subscriptionsController)
+  });
+
   // POST /api/subscriptions/checkout - Create Stripe checkout session
   fastify.post('/subscriptions/checkout', {
     preHandler: [fastify.authenticate],
diff --git a/backend/src/features/subscriptions/domain/subscriptions.service.ts b/backend/src/features/subscriptions/domain/subscriptions.service.ts
index e760f0f..4a2665e 100644
--- a/backend/src/features/subscriptions/domain/subscriptions.service.ts
+++ b/backend/src/features/subscriptions/domain/subscriptions.service.ts
@@ -15,7 +15,9 @@ import {
   BillingCycle,
   SubscriptionStatus,
   UpdateSubscriptionData,
+  NeedsVehicleSelectionResponse,
 } from './subscriptions.types';
+import { VehiclesRepository } from '../../vehicles/data/vehicles.repository';
 
 interface StripeWebhookEvent {
   id: string;
@@ -27,6 +29,7 @@ interface StripeWebhookEvent {
 
 export class SubscriptionsService {
   private userProfileRepository: UserProfileRepository;
+  private vehiclesRepository: VehiclesRepository;
 
   constructor(
     private repository: SubscriptionsRepository,
@@ -34,6 +37,7 @@ export class SubscriptionsService {
     pool: Pool
   ) {
     this.userProfileRepository = new UserProfileRepository(pool);
+    this.vehiclesRepository = new VehiclesRepository(pool);
   }
 
   /**
@@ -57,6 +61,65 @@ export class SubscriptionsService {
     }
   }
 
+  /**
+   * Check if user needs to make a vehicle selection after auto-downgrade
+   * Returns true if: user is on free tier, has >2 vehicles, and hasn't made selections
+   */
+  async checkNeedsVehicleSelection(userId: string): Promise<NeedsVehicleSelectionResponse> {
+    const FREE_TIER_VEHICLE_LIMIT = 2;
+
+    try {
+      // Get current subscription
+      const subscription = await this.repository.findByUserId(userId);
+
+      // No subscription or not on free tier = no selection needed
+      if (!subscription || subscription.tier !== 'free') {
+        return {
+          needsSelection: false,
+          vehicleCount: 0,
+          maxAllowed: FREE_TIER_VEHICLE_LIMIT,
+        };
+      }
+
+      // Count user's active vehicles
+      const vehicleCount = await this.vehiclesRepository.countByUserId(userId);
+
+      // If within limit, no selection needed
+      if (vehicleCount <= FREE_TIER_VEHICLE_LIMIT) {
+        return {
+          needsSelection: false,
+          vehicleCount,
+          maxAllowed: FREE_TIER_VEHICLE_LIMIT,
+        };
+      }
+
+      // Check if user already has vehicle selections
+      const existingSelections = await this.repository.findVehicleSelectionsByUserId(userId);
+
+      // If user already made selections, no selection needed
+      if (existingSelections.length > 0) {
+        return {
+          needsSelection: false,
+          vehicleCount,
+          maxAllowed: FREE_TIER_VEHICLE_LIMIT,
+        };
+      }
+
+      // User is on free tier, has >2 vehicles, and hasn't made selections
+      return {
+        needsSelection: true,
+        vehicleCount,
+        maxAllowed: FREE_TIER_VEHICLE_LIMIT,
+      };
+    } catch (error: any) {
+      logger.error('Failed to check needs vehicle selection', {
+        userId,
+        error: error.message,
+      });
+      throw error;
+    }
+  }
+
   /**
    * Create new subscription (Stripe customer + initial free tier record)
    */
diff --git a/backend/src/features/subscriptions/domain/subscriptions.types.ts b/backend/src/features/subscriptions/domain/subscriptions.types.ts
index 2bcab80..1d6ca83 100644
--- a/backend/src/features/subscriptions/domain/subscriptions.types.ts
+++ b/backend/src/features/subscriptions/domain/subscriptions.types.ts
@@ -131,3 +131,10 @@ export interface UpdateSubscriptionData {
 export interface UpdateDonationData {
   status?: DonationStatus;
 }
+
+// Needs vehicle selection check response
+export interface NeedsVehicleSelectionResponse {
+  needsSelection: boolean;
+  vehicleCount: number;
+  maxAllowed: number;
+}