diff --git a/apps/sim/lib/billing/webhooks/stripe-invoice-webhooks.ts b/apps/sim/lib/billing/webhooks/stripe-invoice-webhooks.ts
index 94ffaac234..7cf1b46c4a 100644
--- a/apps/sim/lib/billing/webhooks/stripe-invoice-webhooks.ts
+++ b/apps/sim/lib/billing/webhooks/stripe-invoice-webhooks.ts
@@ -18,27 +18,75 @@ export async function handleInvoicePaymentSucceeded(event: Stripe.Event) {
   try {
     const invoice = event.data.object as Stripe.Invoice
 
-    // Check if this is an overage billing invoice
-    if (invoice.metadata?.type !== 'overage_billing') {
-      logger.info('Ignoring non-overage billing invoice', { invoiceId: invoice.id })
+    // Case 1: Overage invoices (metadata.type === 'overage_billing')
+    if (invoice.metadata?.type === 'overage_billing') {
+      const customerId = invoice.customer as string
+      const chargedAmount = invoice.amount_paid / 100
+      const billingPeriod = invoice.metadata?.billingPeriod || 'unknown'
+
+      logger.info('Overage billing invoice payment succeeded', {
+        invoiceId: invoice.id,
+        customerId,
+        chargedAmount,
+        billingPeriod,
+        customerEmail: invoice.customer_email,
+        hostedInvoiceUrl: invoice.hosted_invoice_url,
+      })
+
       return
     }
 
-    const customerId = invoice.customer as string
-    const chargedAmount = invoice.amount_paid / 100 // Convert from cents to dollars
-    const billingPeriod = invoice.metadata?.billingPeriod || 'unknown'
+    // Case 2: Subscription renewal invoice paid (primary period rollover)
+    // Only reset on successful payment to avoid granting a new period while in dunning
+    if (invoice.subscription) {
+      // Filter to subscription-cycle renewals; ignore updates/off-cycle charges
+      const reason = invoice.billing_reason
+      const isCycle = reason === 'subscription_cycle'
+      if (!isCycle) {
+        logger.info('Ignoring non-cycle subscription invoice on payment_succeeded', {
+          invoiceId: invoice.id,
+          billingReason: reason,
+        })
+        return
+      }
 
-    logger.info('Overage billing invoice payment succeeded', {
-      invoiceId: invoice.id,
-      customerId,
-      chargedAmount,
-      billingPeriod,
-      customerEmail: invoice.customer_email,
-      hostedInvoiceUrl: invoice.hosted_invoice_url,
-    })
+      const stripeSubscriptionId = String(invoice.subscription)
+      const records = await db
+        .select()
+        .from(subscriptionTable)
+        .where(eq(subscriptionTable.stripeSubscriptionId, stripeSubscriptionId))
+        .limit(1)
 
-    // Additional payment success logic can be added here
-    // For example: update internal billing status, trigger analytics events, etc.
+      if (records.length === 0) {
+        logger.warn('No matching internal subscription for paid Stripe invoice', {
+          invoiceId: invoice.id,
+          stripeSubscriptionId,
+        })
+        return
+      }
+
+      const sub = records[0]
+
+      if (sub.plan === 'team' || sub.plan === 'enterprise') {
+        await resetOrganizationBillingPeriod(sub.referenceId)
+        logger.info('Reset organization billing period on subscription invoice payment', {
+          invoiceId: invoice.id,
+          organizationId: sub.referenceId,
+          plan: sub.plan,
+        })
+      } else {
+        await resetUserBillingPeriod(sub.referenceId)
+        logger.info('Reset user billing period on subscription invoice payment', {
+          invoiceId: invoice.id,
+          userId: sub.referenceId,
+          plan: sub.plan,
+        })
+      }
+
+      return
+    }
+
+    logger.info('Ignoring non-subscription invoice payment', { invoiceId: invoice.id })
   } catch (error) {
     logger.error('Failed to handle invoice payment succeeded', {
       eventId: event.id,
@@ -105,67 +153,20 @@ export async function handleInvoicePaymentFailed(event: Stripe.Event) {
 export async function handleInvoiceFinalized(event: Stripe.Event) {
   try {
     const invoice = event.data.object as Stripe.Invoice
-
-    // Case 1: Overage invoices (metadata.type === 'overage_billing')
+    // Do not reset usage on finalized; wait for payment success to avoid granting new period during dunning
     if (invoice.metadata?.type === 'overage_billing') {
       const customerId = invoice.customer as string
       const invoiceAmount = invoice.amount_due / 100
       const billingPeriod = invoice.metadata?.billingPeriod || 'unknown'
-
       logger.info('Overage billing invoice finalized', {
         invoiceId: invoice.id,
         customerId,
         invoiceAmount,
         billingPeriod,
-        customerEmail: invoice.customer_email,
-        hostedInvoiceUrl: invoice.hosted_invoice_url,
       })
-
       return
     }
-
-    // Case 2: Subscription cycle invoices (primary period rollover)
-    // When an invoice is finalized for a subscription cycle, align our usage reset to this boundary
-    if (invoice.subscription) {
-      const stripeSubscriptionId = String(invoice.subscription)
-
-      const records = await db
-        .select()
-        .from(subscriptionTable)
-        .where(eq(subscriptionTable.stripeSubscriptionId, stripeSubscriptionId))
-        .limit(1)
-
-      if (records.length === 0) {
-        logger.warn('No matching internal subscription for Stripe invoice subscription', {
-          invoiceId: invoice.id,
-          stripeSubscriptionId,
-        })
-        return
-      }
-
-      const sub = records[0]
-
-      // Idempotent reset aligned to the subscription’s new cycle
-      if (sub.plan === 'team' || sub.plan === 'enterprise') {
-        await resetOrganizationBillingPeriod(sub.referenceId)
-        logger.info('Reset organization billing period on subscription invoice finalization', {
-          invoiceId: invoice.id,
-          organizationId: sub.referenceId,
-          plan: sub.plan,
-        })
-      } else {
-        await resetUserBillingPeriod(sub.referenceId)
-        logger.info('Reset user billing period on subscription invoice finalization', {
-          invoiceId: invoice.id,
-          userId: sub.referenceId,
-          plan: sub.plan,
-        })
-      }
-
-      return
-    }
-
-    logger.info('Ignoring non-subscription invoice finalization', {
+    logger.info('Ignoring subscription invoice finalization; will act on payment_succeeded', {
       invoiceId: invoice.id,
       billingReason: invoice.billing_reason,
     })