fix

src/stripe/stripe-webhook.controller.ts

@@ -97,19 +97,38 @@ export class StripeWebhookController {
       return;
     }
 
-    // Check if user already has an active subscription (prevent duplicates)
+    // Check if user already has an active subscription with this same Stripe ID
+    // (prevent true duplicates only — new Stripe subscriptions for same user are allowed
+    // because createCheckoutSession cleanup handles stale records)
     const existingActive = await this.subscriptionService.getActivePlan(userId);
-    if (existingActive) {
-      this.logger.log(`User ${userId} already has active subscription ${existingActive.id}, skipping duplicate`);
+    if (existingActive && existingActive.stripeSubscriptionId === stripeSubscriptionId) {
+      this.logger.log(`User ${userId} already has this exact active subscription, skipping duplicate`);
       return;
     }
 
+    // Fetch full subscription from Stripe to get period dates immediately
+    let currentPeriodStart: Date | undefined;
+    let currentPeriodEnd: Date | undefined;
+    try {
+      const stripeSub: any = await this.stripeService.getStripe().subscriptions.retrieve(stripeSubscriptionId);
+      if (stripeSub.current_period_start) {
+        currentPeriodStart = new Date(stripeSub.current_period_start * 1000);
+      }
+      if (stripeSub.current_period_end) {
+        currentPeriodEnd = new Date(stripeSub.current_period_end * 1000);
+      }
+    } catch (err: any) {
+      this.logger.warn(`Could not fetch Stripe subscription ${stripeSubscriptionId}: ${err.message}`);
+    }
+
     await this.subscriptionService.createSubscription({
       userId,
       planId,
       stripeCustomerId,
       stripeSubscriptionId,
       status: SubscriptionStatus.ACTIVE,
+      currentPeriodStart,
+      currentPeriodEnd,
     });
 
     this.logger.log(`Created subscription for user ${userId}, plan ${planId}`);

src/stripe/stripe.service.ts

@@ -24,7 +24,7 @@ export class StripeService {
     }
   }
 
-  private getStripe(): Stripe {
+  getStripe(): Stripe {
     if (!this.stripe) {
       throw new BadRequestException(
         'Stripe is not configured. Please set STRIPE_SECRET_KEY in environment.',
@@ -71,21 +71,31 @@ export class StripeService {
       throw new BadRequestException('Invalid or inactive plan');
     }
 
-    // Check if user already has an active subscription
-    const activeSubscription = await this.prisma.agentSubscription.findFirst({
-      where: { userId, status: 'ACTIVE' },
+    // Check if user has a VALID active subscription (ACTIVE with valid period end in the future)
+    const now = new Date();
+    const validActive = await this.prisma.agentSubscription.findFirst({
+      where: {
+        userId,
+        status: 'ACTIVE',
+        currentPeriodEnd: { gt: now },
+      },
     });
 
-    if (activeSubscription) {
+    if (validActive) {
       throw new BadRequestException('You already have an active subscription');
     }
 
-    // Clean up any incomplete/failed subscriptions to prevent duplicates
-    // when user retries payment after a previous failure
+    // Clean up stale subscriptions (failed states OR ACTIVE with no period / expired period)
+    // This handles the case where checkout completed but invoice.paid never fired,
+    // leaving an orphaned ACTIVE record without proper period dates
     const staleSubscriptions = await this.prisma.agentSubscription.findMany({
       where: {
         userId,
-        status: { in: ['INCOMPLETE', 'UNPAID', 'PAST_DUE'] },
+        OR: [
+          { status: { in: ['INCOMPLETE', 'UNPAID', 'PAST_DUE', 'CANCELED'] } },
+          { status: 'ACTIVE', currentPeriodEnd: null },
+          { status: 'ACTIVE', currentPeriodEnd: { lte: now } },
+        ],
       },
     });
 
@@ -101,8 +111,7 @@ export class StripeService {
       }
       await this.prisma.agentSubscription.deleteMany({
         where: {
-          userId,
-          status: { in: ['INCOMPLETE', 'UNPAID', 'PAST_DUE'] },
+          id: { in: staleSubscriptions.map((s) => s.id) },
         },
       });
       this.logger.log(`Cleaned up ${staleSubscriptions.length} stale subscription(s) for user ${userId}`);