diff --git a/apps/backend/src/api/routes/billing.controller.ts b/apps/backend/src/api/routes/billing.controller.ts
index 039513fb..2ba8eb1f 100644
--- a/apps/backend/src/api/routes/billing.controller.ts
+++ b/apps/backend/src/api/routes/billing.controller.ts
@@ -9,6 +9,7 @@ import { GetUserFromRequest } from '@gitroom/nestjs-libraries/user/user.from.req
 import { NotificationService } from '@gitroom/nestjs-libraries/database/prisma/notifications/notification.service';
 import { Request } from 'express';
 import { Nowpayments } from '@gitroom/nestjs-libraries/crypto/nowpayments';
+import { AuthService } from '@gitroom/helpers/auth/auth.service';
 
 @ApiTags('Billing')
 @Controller('/billing')
@@ -30,6 +31,20 @@ export class BillingController {
     };
   }
 
+  @Get('/check-discount')
+  async checkDiscount(@GetOrgFromRequest() org: Organization) {
+    return {
+      offerCoupon: !(await this._stripeService.checkDiscount(org.paymentId))
+        ? false
+        : AuthService.signJWT({ discount: true }),
+    };
+  }
+
+  @Post('/apply-discount')
+  async applyDiscount(@GetOrgFromRequest() org: Organization) {
+    await this._stripeService.applyDiscount(org.paymentId);
+  }
+
   @Post('/finish-trial')
   async finishTrial(@GetOrgFromRequest() org: Organization) {
     try {
diff --git a/apps/frontend/src/components/billing/main.billing.component.tsx b/apps/frontend/src/components/billing/main.billing.component.tsx
index 3485012a..a52b6e63 100644
--- a/apps/frontend/src/components/billing/main.billing.component.tsx
+++ b/apps/frontend/src/components/billing/main.billing.component.tsx
@@ -135,6 +135,38 @@ export const Features: FC<{
     </div>
   );
 };
+
+const Accept: FC<{ resolve: (res: boolean) => void }> = ({ resolve }) => {
+  const [loading, setLoading] = useState(false);
+  const fetch = useFetch();
+  const toaster = useToaster();
+
+  const apply = useCallback(async () => {
+    setLoading(true);
+    await fetch('/billing/apply-discount', {
+      method: 'POST',
+    });
+
+    resolve(true);
+    toaster.show('50% discount applied successfully');
+  }, []);
+
+  return (
+    <div>
+      <div className="mb-[20px]">
+        Would you accept 50% discount for 3 months instead? 🙏🏻
+      </div>
+      <div className="flex gap-[10px]">
+        <Button loading={loading} onClick={apply}>
+          Apply 50% discount for 3 months
+        </Button>
+        <Button onClick={() => resolve(false)} className="!bg-red-800">
+          Cancel my subscription
+        </Button>
+      </div>
+    </div>
+  );
+};
 const Info: FC<{
   proceed: (feedback: string) => void;
 }> = (props) => {
@@ -277,13 +309,34 @@ export const MainBillingComponent: FC<{
           if (
             subscription?.cancelAt ||
             (await deleteDialog(
-              `Are you sure you want to cancel your subscription? ${messages.join(
-                ', '
-              )}`,
+              `Are you sure you want to cancel your subscription?
+              ${messages.join(', ')}`,
               'Yes, cancel',
               'Cancel Subscription'
             ))
           ) {
+            const checkDiscount = await (
+              await fetch('/billing/check-discount')
+            ).json();
+            if (checkDiscount.offerCoupon) {
+              const info = await new Promise((res) => {
+                modal.openModal({
+                  title: 'Before you cancel',
+                  withCloseButton: true,
+                  classNames: {
+                    modal: 'bg-transparent text-textColor',
+                  },
+                  children: <Accept resolve={res} />,
+                });
+              });
+
+              modal.closeAll();
+
+              if (info) {
+                return;
+              }
+            }
+
             const info = await new Promise((res) => {
               modal.openModal({
                 title: t(
@@ -297,6 +350,7 @@ export const MainBillingComponent: FC<{
                 children: <Info proceed={(e) => res(e)} />,
               });
             });
+
             setLoading(true);
             const { cancel_at } = await (
               await fetch('/billing/cancel', {
diff --git a/libraries/nestjs-libraries/src/services/stripe.service.ts b/libraries/nestjs-libraries/src/services/stripe.service.ts
index 5a7f5949..e27e0a8b 100644
--- a/libraries/nestjs-libraries/src/services/stripe.service.ts
+++ b/libraries/nestjs-libraries/src/services/stripe.service.ts
@@ -475,6 +475,72 @@ export class StripeService {
     });
   }
 
+  async checkDiscount(customer: string) {
+    if (!process.env.STRIPE_DISCOUNT_ID) {
+      return false;
+    }
+
+    const list = await stripe.charges.list({
+      customer,
+      limit: 1,
+    });
+
+    if (!list.data.filter(f => f.amount > 1000).length) {
+      return false;
+    }
+
+    const currentUserSubscription = {
+      data: (
+        await stripe.subscriptions.list({
+          customer,
+          status: 'all',
+          expand: ['data.discounts'],
+        })
+      ).data.find((f) => f.status === 'active' || f.status === 'trialing'),
+    };
+
+    if (!currentUserSubscription) {
+      return false;
+    }
+
+    if (
+      currentUserSubscription.data?.items.data[0]?.price.recurring?.interval ===
+        'year' ||
+      currentUserSubscription.data?.discounts.length
+    ) {
+      return false;
+    }
+
+    return true;
+  }
+
+  async applyDiscount(customer: string) {
+    const check = this.checkDiscount(customer);
+    if (!check) {
+      return false;
+    }
+
+    const currentUserSubscription = {
+      data: (
+        await stripe.subscriptions.list({
+          customer,
+          status: 'all',
+          expand: ['data.discounts'],
+        })
+      ).data.find((f) => f.status === 'active' || f.status === 'trialing'),
+    };
+
+    await stripe.subscriptions.update(currentUserSubscription.data.id, {
+      discounts: [
+        {
+          coupon: process.env.STRIPE_DISCOUNT_ID!,
+        },
+      ],
+    });
+
+    return true;
+  }
+
   async checkSubscription(organizationId: string, subscriptionId: string) {
     const orgValue = await this._subscriptionService.checkSubscription(
       organizationId,