diff --git a/apps/node-fastify/src/test/webhooks.test.ts b/apps/node-fastify/src/test/webhooks.test.ts
index 1a307d6..ca1ee39 100644
--- a/apps/node-fastify/src/test/webhooks.test.ts
+++ b/apps/node-fastify/src/test/webhooks.test.ts
@@ -1,4 +1,4 @@
-import { describe, it, expect, beforeAll, afterAll } from 'vitest';
+import { describe, it, expect, beforeAll, afterAll, vi, afterEach } from 'vitest';
 import { FastifyInstance } from 'fastify';
 import path from 'node:path';
 import pino from 'pino';
@@ -18,6 +18,7 @@ describe('POST /webhooks', () => {
   let orbSync: OrbSync;
 
   beforeAll(async () => {
+    process.env.TZ = 'UTC'; // Ensure consistent timezone for tests
     const logger = pino({ level: 'silent' });
 
     // Create a OrbSync instance for integration testing
@@ -45,6 +46,10 @@ describe('POST /webhooks', () => {
     }
   });
 
+  afterEach(() => {
+    vi.restoreAllMocks();
+  });
+
   function loadWebhookPayload(eventName: string): string {
     const fixturePath = path.join(__dirname, 'orb', `${eventName}.json`);
     return fs.readFileSync(fixturePath, 'utf-8');
@@ -171,6 +176,86 @@ describe('POST /webhooks', () => {
     );
   });
 
+  it('should handle invoice.issued webhook and resync subscription if billing cycle outdated', async () => {
+    let payload = loadWebhookPayload('invoice');
+
+    // Parse the payload and update billing cycle dates to sensible values
+    const webhookData = JSON.parse(payload);
+    const invoiceId = webhookData.invoice.id;
+    const subscriptionId = webhookData.invoice.subscription?.id;
+    const customerId = webhookData.invoice.customer.id;
+
+    // As preparation, we delete the existing invoice and subscription if they exist
+    await deleteTestData(orbSync.postgresClient, 'invoices', [invoiceId]);
+    await deleteTestData(orbSync.postgresClient, 'subscriptions', [subscriptionId]);
+
+    webhookData.type = 'invoice.issued';
+
+    const now = new Date();
+    const oneDayAgo = new Date(now.getTime() - 24 * 60 * 60 * 1000); // 1 day ago
+    const thirtyOneDaysAgo = new Date(now.getTime() - 31 * 24 * 60 * 60 * 1000); // 31 days ago
+    const thirtyDaysInFuture = new Date(now.getTime() + 30 * 24 * 60 * 60 * 1000); // 30 days in future
+
+    // Find and update the plan and change to in_arrear
+    const planLineItem = webhookData.invoice.line_items.find(
+      (item: Invoice.LineItem) =>
+        item.price?.price_type === 'fixed_price' && item.price.billable_metric === null && item.name.endsWith('Plan')
+    );
+    planLineItem.price.billing_mode = 'in_arrear';
+
+    // Update the payload with the modified data
+    payload = JSON.stringify(webhookData);
+
+    // For an outdated billing cycle, the webhook handler resyncs the subscription from the Orb API
+    // to get the new billing cycle. We mock that fetch to return the subscription with the
+    // updated billing period dates.
+    const testSubscription = {
+      id: subscriptionId,
+      customer: { id: customerId },
+      status: 'active',
+      current_billing_period_start_date: thirtyOneDaysAgo.toISOString(),
+      // Billing cycle end date in past
+      current_billing_period_end_date: oneDayAgo.toISOString(),
+      billing_cycle_day: 8,
+      net_terms: 0,
+      metadata: {},
+      created_at: new Date().toISOString(),
+      start_date: new Date().toISOString(),
+    } as Subscription;
+
+    syncSubscriptions(orbSync.postgresClient, [testSubscription]);
+
+    // Mock the Orb SDK call that fetches the subscription during the in-arrears resync
+    const orb = (orbSync as unknown as { orb: { subscriptions: { fetch: (id: string) => Promise<Subscription> } } })
+      .orb;
+
+    const latestSubscription = {
+      ...testSubscription,
+      current_billing_period_start_date: oneDayAgo.toISOString(),
+      current_billing_period_end_date: thirtyDaysInFuture.toISOString(),
+    };
+    const fetchSpy = vi.spyOn(orb.subscriptions, 'fetch').mockResolvedValue(latestSubscription);
+
+    const response = await sendWebhookRequest(payload);
+    expect(fetchSpy).toHaveBeenCalledWith(subscriptionId);
+    expect(response.statusCode).toBe(200);
+
+    // Verify that the invoice was created in the database
+    const [invoice] = await fetchInvoicesFromDatabase(orbSync.postgresClient, [invoiceId]);
+    expect(invoice).toBeDefined();
+
+    // Verify that billing cycle was updated if subscription exists and has a plan line item
+    const billingCycles = await fetchBillingCyclesFromDatabase(orbSync.postgresClient, subscriptionId);
+    expect(billingCycles).toHaveLength(1);
+    const billingCycle = billingCycles[0];
+
+    // The billing cycle should reflect the resynced subscription's billing period (startDate/endDate),
+    // proving the in-arrears branch fetched the subscription from the Orb API rather than deriving the
+    // cycle from the invoice line item.
+    expect(new Date(billingCycle.current_billing_period_start_date).toISOString()).toBe(oneDayAgo.toISOString());
+    expect(new Date(billingCycle.current_billing_period_end_date).toISOString()).toBe(thirtyDaysInFuture.toISOString());
+  });
+
   it.each([
     'invoice.edited',
     'invoice.manually_marked_as_void',
diff --git a/packages/orb-sync-lib/src/database/postgres.ts b/packages/orb-sync-lib/src/database/postgres.ts
index 7c33c0a..afa2767 100644
--- a/packages/orb-sync-lib/src/database/postgres.ts
+++ b/packages/orb-sync-lib/src/database/postgres.ts
@@ -178,6 +178,22 @@ export class PostgresClient {
     return result.rows;
   }
 
+  async getBillingCycleEndDate(subscriptionId: string): Promise<string | null> {
+    const query = `
+      select  current_billing_period_end_date
+      from "${this.config.schema}"."subscriptions"
+      where id = $1 and status = 'active'
+    `;
+
+    const result = await this.pool.query(query, [subscriptionId]);
+
+    if (!result.rows.length) {
+      return null;
+    }
+
+    return result.rows[0].current_billing_period_end_date;
+  }
+
   async query(text: string, params?: string[]): Promise<QueryResult> {
     return this.pool.query(text, params);
   }
diff --git a/packages/orb-sync-lib/src/invoice-utils.ts b/packages/orb-sync-lib/src/invoice-utils.ts
index 911b050..ec64f1b 100644
--- a/packages/orb-sync-lib/src/invoice-utils.ts
+++ b/packages/orb-sync-lib/src/invoice-utils.ts
@@ -6,7 +6,9 @@ const PLAN_LINE_ITEM_NAME_ENDS_IN = 'Plan';
  * Returns the billing cycle the given invoice's plan line item applies to.
  * If no plan line item is present, null is returned.
  */
-export function getBillingCycleFromInvoice(invoice: Invoice): { start: string; end: string } | null {
+export function getBillingCycleFromInvoice(
+  invoice: Invoice
+): { start: string; end: string; inArrears: boolean } | null {
   const planLineItem = findPlanLineItem(invoice.line_items);
 
   // No plan line item found.
@@ -19,6 +21,7 @@ export function getBillingCycleFromInvoice(invoice: Invoice): { start: string; e
   return {
     start: planLineItem.start_date,
     end: planLineItem.end_date,
+    inArrears: planLineItem.price?.billing_mode === 'in_arrear',
   };
 }
 
diff --git a/packages/orb-sync-lib/src/orb-sync.ts b/packages/orb-sync-lib/src/orb-sync.ts
index ac9936c..2f90fce 100644
--- a/packages/orb-sync-lib/src/orb-sync.ts
+++ b/packages/orb-sync-lib/src/orb-sync.ts
@@ -18,6 +18,7 @@ import type {
 import { PostgresClient } from './database/postgres';
 import { fetchAndSyncCustomer, fetchAndSyncCustomers, syncCustomers } from './sync/customers';
 import {
+  checkIfCurrentBillingCycleIsOutdated,
   fetchAndSyncSubscription,
   fetchAndSyncSubscriptions,
   syncSubscriptions,
@@ -226,12 +227,23 @@ export class OrbSync {
         await syncInvoices(this.postgresClient, [invoice], webhook.created_at);
 
         const billingCycle = getBillingCycleFromInvoice(invoice);
-        if (billingCycle && invoice.subscription) {
+        if (billingCycle && invoice.subscription && !billingCycle.inArrears) {
           await updateBillingCycle(this.postgresClient, {
             subscriptionId: invoice.subscription.id,
             billingCycleStart: billingCycle.start,
             billingCycleEnd: billingCycle.end,
           });
+        } else if ((billingCycle?.inArrears || !billingCycle) && invoice.subscription) {
+          // In case no plan item is present, we still want to do a check to see if there is an outdated billing cycle and potentially trigger an update
+          const isOutdated = await checkIfCurrentBillingCycleIsOutdated(this.postgresClient, invoice.subscription.id);
+
+          if (isOutdated) {
+            this.config.logger?.info(
+              `Billing cycle of subscription ${invoice.subscription.id} is outdated, fetching latest subscription data from Orb API to update it`
+            );
+            const subscription = await this.orb.subscriptions.fetch(invoice.subscription.id);
+            await syncSubscriptions(this.postgresClient, [subscription]);
+          }
         }
 
         break;
diff --git a/packages/orb-sync-lib/src/sync/subscriptions.ts b/packages/orb-sync-lib/src/sync/subscriptions.ts
index 182a165..ea0642e 100644
--- a/packages/orb-sync-lib/src/sync/subscriptions.ts
+++ b/packages/orb-sync-lib/src/sync/subscriptions.ts
@@ -83,3 +83,17 @@ export async function updateBillingCycle(
 
   return postgresClient.updateSubscriptionBillingCycle({ subscriptionId, billingCycleStart, billingCycleEnd });
 }
+
+export async function checkIfCurrentBillingCycleIsOutdated(
+  postgresClient: PostgresClient,
+  subscriptionId: string
+): Promise<boolean> {
+  const billingCycleEndDate = await postgresClient.getBillingCycleEndDate(subscriptionId);
+
+  if (!billingCycleEndDate) {
+    // If none is found, no need to update it, perhaps already deleted sub
+    return false;
+  }
+
+  return new Date(billingCycleEndDate).getTime() < new Date().getTime();
+}