diff --git a/packages/fastify-app/src/test/subscriptionTimestampTieBreak.test.ts b/packages/fastify-app/src/test/subscriptionTimestampTieBreak.test.ts
new file mode 100644
index 000000000..bde8bf885
--- /dev/null
+++ b/packages/fastify-app/src/test/subscriptionTimestampTieBreak.test.ts
@@ -0,0 +1,93 @@
+import type Stripe from 'stripe'
+import { StripeSync, runMigrations } from '@supabase/stripe-sync-engine'
+import { afterAll, afterEach, beforeAll, describe, expect, test, vitest } from 'vitest'
+import { getConfig } from '../utils/config'
+import { mockStripe } from './helpers/mockStripe'
+import { logger } from '../logger'
+
+let stripeSync: StripeSync
+let schema: string
+
+beforeAll(async () => {
+  process.env.REVALIDATE_OBJECTS_VIA_STRIPE_API = ''
+  process.env.BACKFILL_RELATED_ENTITIES = 'false'
+
+  const config = getConfig()
+  schema = config.schema
+
+  await runMigrations({
+    databaseUrl: config.databaseUrl,
+    schema: config.schema,
+    logger,
+  })
+
+  stripeSync = new StripeSync({
+    ...config,
+    poolConfig: {
+      connectionString: config.databaseUrl,
+    },
+  })
+  const stripe = Object.assign(stripeSync.stripe, mockStripe)
+  vitest.spyOn(stripeSync, 'stripe', 'get').mockReturnValue(stripe)
+})
+
+afterEach(() => {
+  vitest.clearAllMocks()
+})
+
+afterAll(async () => {
+  if (stripeSync) {
+    await stripeSync.close()
+  }
+})
+
+describe('subscription tie-break on same timestamp', () => {
+  test('refetches subscription when same-second event would otherwise be skipped', async () => {
+    const baseEvent = await import('./stripe/subscription_created.json').then(
+      ({ default: data }) => data
+    )
+    const sameTimestamp = Math.floor(Date.now() / 1000)
+    const subscriptionId = baseEvent.data.object.id
+
+    await stripeSync.postgresClient.query(
+      `delete from "${schema}"."subscription_items" where subscription = $1`,
+      [subscriptionId]
+    )
+    await stripeSync.postgresClient.query(`delete from "${schema}"."subscriptions" where id = $1`, [
+      subscriptionId,
+    ])
+
+    const trialEvent = structuredClone(baseEvent)
+    trialEvent.id = 'evt_tie_trial'
+    trialEvent.type = 'customer.subscription.trial_will_end'
+    trialEvent.created = sameTimestamp
+    trialEvent.data.object.status = 'trialing'
+    trialEvent.data.object.billing_cycle_anchor = 100
+
+    const updatedEvent = structuredClone(baseEvent)
+    updatedEvent.id = 'evt_tie_updated'
+    updatedEvent.type = 'customer.subscription.updated'
+    updatedEvent.created = sameTimestamp
+    updatedEvent.data.object.status = 'active'
+    updatedEvent.data.object.billing_cycle_anchor = 200
+
+    mockStripe.subscriptions.retrieve.mockResolvedValueOnce({
+      ...updatedEvent.data.object,
+      billing_cycle_anchor: 300,
+      status: 'active',
+    })
+
+    await stripeSync.processEvent(trialEvent as Stripe.Event)
+    await stripeSync.processEvent(updatedEvent as Stripe.Event)
+
+    const result = await stripeSync.postgresClient.query(
+      `select id, status, billing_cycle_anchor from "${schema}"."subscriptions" where id = $1`,
+      [subscriptionId]
+    )
+
+    expect(result.rows.length).toBe(1)
+    expect(result.rows[0].status).toBe('active')
+    expect(result.rows[0].billing_cycle_anchor).toBe(300)
+    expect(mockStripe.subscriptions.retrieve).toHaveBeenCalledTimes(1)
+  })
+})
diff --git a/packages/sync-engine/src/stripeSync.ts b/packages/sync-engine/src/stripeSync.ts
index 441bc90d4..e33e1da00 100644
--- a/packages/sync-engine/src/stripeSync.ts
+++ b/packages/sync-engine/src/stripeSync.ts
@@ -189,15 +189,22 @@ export class StripeSync {
           (subscription) =>
             subscription.status === 'canceled' || subscription.status === 'incomplete_expired'
         )
+        const syncTimestamp = this.getSyncTimestamp(event, refetched)
 
         this.config.logger?.info(
           `Received webhook ${event.id}: ${event.type} for subscription ${subscription.id}`
         )
 
-        await this.upsertSubscriptions(
+        const upsertedSubscriptions = await this.upsertSubscriptions(
           [subscription],
           false,
-          this.getSyncTimestamp(event, refetched)
+          syncTimestamp
+        )
+        await this.resolveEqualTimestampSubscriptionConflict(
+          subscription.id,
+          upsertedSubscriptions,
+          refetched,
+          syncTimestamp
         )
         break
       }
@@ -581,6 +588,32 @@ export class StripeSync {
     return refetched ? new Date().toISOString() : new Date(event.created * 1000).toISOString()
   }
 
+  private async resolveEqualTimestampSubscriptionConflict(
+    subscriptionId: string,
+    upsertedSubscriptions: Stripe.Subscription[],
+    refetched: boolean,
+    syncTimestamp: string
+  ) {
+    if (refetched || upsertedSubscriptions.length > 0) return
+
+    const query = `
+      select 1
+      from "${this.config.schema}"."subscriptions"
+      where id = $1
+        and last_synced_at = $2::timestamptz
+      limit 1
+    `
+    const result = await this.postgresClient.query(query, [subscriptionId, syncTimestamp])
+    if (!result.rows.length) return
+
+    this.config.logger?.warn(
+      `Equal timestamp detected for subscription ${subscriptionId}. Refetching from Stripe for deterministic state.`
+    )
+
+    const latestSubscription = await this.stripe.subscriptions.retrieve(subscriptionId)
+    await this.upsertSubscriptions([latestSubscription], false, new Date().toISOString())
+  }
+
   private shouldRefetchEntity(entity: { object: string }) {
     return this.config.revalidateObjectsViaStripeApi?.includes(entity.object as RevalidateEntity)
   }