diff --git a/packages/twenty-website/.env.example b/packages/twenty-website/.env.example
index 473f15f729..8d0f6619ec 100644
--- a/packages/twenty-website/.env.example
+++ b/packages/twenty-website/.env.example
@@ -36,6 +36,10 @@ ENTERPRISE_JWT_PUBLIC_KEY=
 # Optional: short-lived validity token length in days (default 30)
 # ENTERPRISE_VALIDITY_TOKEN_DURATION_DAYS=
 
+# Shared secret guarding the internal enterprise key reissue support endpoint,
+# used to regenerate an enterprise key
+ENTERPRISE_ADMIN_API_SECRET=
+
 # Twenty workspace the partners marketplace reads partner data from
 # (server-side only) via the /s/partners REST endpoint.
 TWENTY_PARTNERS_API_URL=
diff --git a/packages/twenty-website/src/app/api/enterprise/activate/route.ts b/packages/twenty-website/src/app/api/enterprise/activate/route.ts
index 1ad37aac67..353017b54f 100644
--- a/packages/twenty-website/src/app/api/enterprise/activate/route.ts
+++ b/packages/twenty-website/src/app/api/enterprise/activate/route.ts
@@ -1,4 +1,5 @@
 import { signEnterpriseKey } from '@/lib/enterprise/enterprise-jwt';
+import { getLicenseeFromStripeCustomer } from '@/lib/enterprise/stripe-customer-helpers';
 import { getStripeClient } from '@/lib/enterprise/stripe-client';
 import { NextResponse } from 'next/server';
 
@@ -59,11 +60,7 @@ export async function GET(request: Request) {
       );
     }
 
-    const customer = session.customer;
-    const licensee =
-      customer && typeof customer !== 'string' && !customer.deleted
-        ? (customer.name ?? customer.email ?? 'Unknown')
-        : 'Unknown';
+    const licensee = getLicenseeFromStripeCustomer(session.customer);
 
     const enterpriseKey = signEnterpriseKey(subscription.id, licensee);
 
diff --git a/packages/twenty-website/src/app/api/enterprise/reissue/route.ts b/packages/twenty-website/src/app/api/enterprise/reissue/route.ts
new file mode 100644
index 0000000000..7e5c339453
--- /dev/null
+++ b/packages/twenty-website/src/app/api/enterprise/reissue/route.ts
@@ -0,0 +1,83 @@
+import * as crypto from 'crypto';
+
+import { signEnterpriseKey } from '@/lib/enterprise/enterprise-jwt';
+import { getStripeClient } from '@/lib/enterprise/stripe-client';
+import { getLicenseeFromStripeCustomer } from '@/lib/enterprise/stripe-customer-helpers';
+import { NextResponse } from 'next/server';
+
+export const dynamic = 'force-dynamic';
+
+const isSecretValid = (providedSecret: string): boolean => {
+  const expectedSecret = process.env.ENTERPRISE_ADMIN_API_SECRET;
+
+  if (!expectedSecret || !providedSecret) {
+    return false;
+  }
+
+  const comparisonKey = crypto.randomBytes(32);
+  const expectedDigest = crypto
+    .createHmac('sha256', comparisonKey)
+    .update(expectedSecret)
+    .digest();
+  const providedDigest = crypto
+    .createHmac('sha256', comparisonKey)
+    .update(providedSecret)
+    .digest();
+
+  return crypto.timingSafeEqual(expectedDigest, providedDigest);
+};
+
+export async function POST(request: Request) {
+  try {
+    let body: { subscriptionId?: unknown; secret?: unknown } = {};
+
+    try {
+      body = await request.json();
+    } catch {
+      body = {};
+    }
+
+    const secret = typeof body.secret === 'string' ? body.secret : '';
+
+    if (!isSecretValid(secret)) {
+      return NextResponse.json({ error: 'Unauthorized' }, { status: 401 });
+    }
+
+    const subscriptionId =
+      typeof body.subscriptionId === 'string' ? body.subscriptionId : '';
+
+    if (!subscriptionId) {
+      return NextResponse.json(
+        { error: 'Missing subscriptionId' },
+        { status: 400 },
+      );
+    }
+
+    const stripe = getStripeClient();
+
+    const subscription = await stripe.subscriptions.retrieve(subscriptionId, {
+      expand: ['customer'],
+    });
+
+    const licensee = getLicenseeFromStripeCustomer(subscription.customer);
+    const enterpriseKey = signEnterpriseKey(subscription.id, licensee);
+
+    const response = NextResponse.json({
+      enterpriseKey,
+      licensee,
+      subscriptionId: subscription.id,
+      subscriptionStatus: subscription.status,
+    });
+
+    response.headers.set('Cache-Control', 'no-store');
+
+    return response;
+  } catch (error: unknown) {
+    console.error('Enterprise key reissue failed', error);
+
+    return NextResponse.json(
+      { error: 'Internal server error' },
+      { status: 500 },
+    );
+  }
+}
diff --git a/packages/twenty-website/src/lib/enterprise/stripe-customer-helpers.ts b/packages/twenty-website/src/lib/enterprise/stripe-customer-helpers.ts
new file mode 100644
index 0000000000..40592e9455
--- /dev/null
+++ b/packages/twenty-website/src/lib/enterprise/stripe-customer-helpers.ts
@@ -0,0 +1,17 @@
+import type Stripe from 'stripe';
+
+type StripeCustomerField =
+  | string
+  | Stripe.Customer
+  | Stripe.DeletedCustomer
+  | null;
+
+export const getLicenseeFromStripeCustomer = (
+  customer: StripeCustomerField,
+): string => {
+  if (customer && typeof customer !== 'string' && !customer.deleted) {
+    return customer.name ?? customer.email ?? 'Unknown';
+  }
+
+  return 'Unknown';
+};