diff --git a/test/api/v3/unit/libs/stripePayments.test.js b/test/api/v3/unit/libs/stripePayments.test.js
index 62d010202c..5ccc4afaf3 100644
--- a/test/api/v3/unit/libs/stripePayments.test.js
+++ b/test/api/v3/unit/libs/stripePayments.test.js
@@ -12,6 +12,7 @@ import payments from '../../../../../website/server/libs/payments';
 import common from '../../../../../website/common';
 import logger from '../../../../../website/server/libs/logger';
 import { v4 as uuid } from 'uuid';
+import moment from 'moment';
 
 const i18n = common.i18n;
 
@@ -878,6 +879,7 @@ describe('Stripe Payments', () => {
           let cancelSubscriptionOpts = payments.cancelSubscription.lastCall.args[0];
           expect(cancelSubscriptionOpts.user._id).to.equal(subscriber._id);
           expect(cancelSubscriptionOpts.paymentMethod).to.equal('Stripe');
+          expect(Math.round(moment(cancelSubscriptionOpts.nextBill).diff(new Date(), 'days', true))).to.equal(3);
           expect(cancelSubscriptionOpts.groupId).to.be.undefined;
 
           stripe.events.retrieve.restore();
@@ -988,6 +990,7 @@ describe('Stripe Payments', () => {
           let cancelSubscriptionOpts = payments.cancelSubscription.lastCall.args[0];
           expect(cancelSubscriptionOpts.user._id).to.equal(leader._id);
           expect(cancelSubscriptionOpts.paymentMethod).to.equal('Stripe');
+          expect(Math.round(moment(cancelSubscriptionOpts.nextBill).diff(new Date(), 'days', true))).to.equal(3);
           expect(cancelSubscriptionOpts.groupId).to.equal(subscriber._id);
 
           stripe.events.retrieve.restore();
diff --git a/website/server/libs/payments.js b/website/server/libs/payments.js
index 4f2d6df15a..0eb94790a0 100644
--- a/website/server/libs/payments.js
+++ b/website/server/libs/payments.js
@@ -424,7 +424,7 @@ api.cancelSubscription = async function cancelSubscription (data) {
     defaultRemainingDays = 2;
   }
 
-  let remaining = data.nextBill ? moment(data.nextBill).diff(new Date(), 'days') : defaultRemainingDays;
+  let remaining = data.nextBill ? moment(data.nextBill).diff(new Date(), 'days', true) : defaultRemainingDays;
   if (plan.extraMonths < 0) plan.extraMonths = 0;
   let extraDays = Math.ceil(30.5 * plan.extraMonths);
   let nowStr = `${now.format('MM')}/${moment(plan.dateUpdated).format('DD')}/${now.format('YYYY')}`;
diff --git a/website/server/libs/stripePayments.js b/website/server/libs/stripePayments.js
index eacd2f143b..d00bcaea0f 100644
--- a/website/server/libs/stripePayments.js
+++ b/website/server/libs/stripePayments.js
@@ -328,6 +328,8 @@ api.handleWebhooks = async function handleWebhooks (options, stripeInc) {
         user,
         groupId,
         paymentMethod: this.constants.PAYMENT_METHOD,
+        // Give three extra days to allow the user to resubscribe without losing benefits
+        nextBill: moment().add({days: 3}).toDate(),
       });
 
       break;