diff --git a/apps/portal/src/utils/helpers.js b/apps/portal/src/utils/helpers.js
index ad60585ed5..7135f3c41e 100644
--- a/apps/portal/src/utils/helpers.js
+++ b/apps/portal/src/utils/helpers.js
@@ -556,15 +556,7 @@ export function subscriptionHasFreeTrial({sub} = {}) {
 }
 
 export function isInThePast(date) {
-    const today = new Date();
-
-    // 👇️ OPTIONAL!
-    // This line sets the hour of the current date to midnight
-    // so the comparison only returns `true` if the passed in date
-    // is at least yesterday
-    today.setHours(0, 0, 0, 0);
-
-    return date < today;
+    return date < new Date();
 }
 
 export function getProductFromPrice({site, priceId}) {
diff --git a/apps/portal/src/utils/helpers.test.js b/apps/portal/src/utils/helpers.test.js
index 85cec013fe..adea069cdb 100644
--- a/apps/portal/src/utils/helpers.test.js
+++ b/apps/portal/src/utils/helpers.test.js
@@ -1,4 +1,4 @@
-import {getAllProductsForSite, getAvailableProducts, getCurrencySymbol, getFreeProduct, getMemberName, getMemberSubscription, getPriceFromSubscription, getPriceIdFromPageQuery, getSupportAddress, getUrlHistory, hasMultipleProducts, isActiveOffer, isInviteOnlySite, isPaidMember, isSameCurrency, transformApiTiersData, isSigninAllowed, isSignupAllowed, getCompExpiry} from './helpers';
+import {getAllProductsForSite, getAvailableProducts, getCurrencySymbol, getFreeProduct, getMemberName, getMemberSubscription, getPriceFromSubscription, getPriceIdFromPageQuery, getSupportAddress, getUrlHistory, hasMultipleProducts, isActiveOffer, isInviteOnlySite, isPaidMember, isSameCurrency, transformApiTiersData, isSigninAllowed, isSignupAllowed, getCompExpiry, isInThePast} from './helpers';
 import * as Fixtures from './fixtures-generator';
 import {site as FixturesSite, member as FixtureMember, offer as FixtureOffer, transformTierFixture as TransformFixtureTiers} from '../utils/test-fixtures';
 import {isComplimentaryMember} from '../utils/helpers';
@@ -448,4 +448,17 @@ describe('Helpers - ', () => {
             expect(getCompExpiry({member})).toEqual('');
         });
     });
+
+    describe('isInThePast', () => {
+        it('returns a boolean indicating if the provided date is in the past', () => {
+            const pastDate = new Date();
+            pastDate.setDate(pastDate.getDate() - 1);
+
+            const futureDate = new Date();
+            futureDate.setDate(futureDate.getDate() + 1);
+
+            expect(isInThePast(pastDate)).toEqual(true);
+            expect(isInThePast(futureDate)).toEqual(false);
+        });
+    });
 });
diff --git a/ghost/members-api/lib/repositories/MemberRepository.js b/ghost/members-api/lib/repositories/MemberRepository.js
index aa8d90797e..e79f1a3604 100644
--- a/ghost/members-api/lib/repositories/MemberRepository.js
+++ b/ghost/members-api/lib/repositories/MemberRepository.js
@@ -21,6 +21,8 @@ const messages = {
     invalidEmail: 'Invalid Email'
 };
 
+const SUBSCRIPTION_STATUS_TRIALING = 'trialing';
+
 /**
  * @typedef {object} ITokenService
  * @prop {(token: string) => Promise<import('jsonwebtoken').JwtPayload>} decodeToken
@@ -1367,6 +1369,10 @@ module.exports = class MemberRepository {
                     data.subscription.price
                 );
                 updatedSubscription = await this._stripeAPIService.removeCouponFromSubscription(subscription.id);
+
+                if (subscriptionModel.get('status') === SUBSCRIPTION_STATUS_TRIALING) {
+                    updatedSubscription = await this._stripeAPIService.cancelSubscriptionTrial(subscription.id);
+                }
             }
         }
 
diff --git a/ghost/stripe/lib/StripeAPI.js b/ghost/stripe/lib/StripeAPI.js
index b03a257c4c..8e0c58bcbd 100644
--- a/ghost/stripe/lib/StripeAPI.js
+++ b/ghost/stripe/lib/StripeAPI.js
@@ -759,4 +759,16 @@ module.exports = class StripeAPI {
             default_payment_method: paymentMethod
         });
     }
+
+    /**
+     * @param {string} id - The ID of the subscription to cancel the trial for
+     *
+     * @returns {Promise<import('stripe').Stripe.Subscription>}
+     */
+    async cancelSubscriptionTrial(id) {
+        await this._rateLimitBucket.throttle();
+        return this._stripe.subscriptions.update(id, {
+            trial_end: 'now'
+        });
+    }
 };
diff --git a/ghost/stripe/test/unit/lib/StripeAPI.test.js b/ghost/stripe/test/unit/lib/StripeAPI.test.js
index fb4e04c990..3382fd2814 100644
--- a/ghost/stripe/test/unit/lib/StripeAPI.test.js
+++ b/ghost/stripe/test/unit/lib/StripeAPI.test.js
@@ -250,4 +250,37 @@ describe('StripeAPI', function () {
             });
         });
     });
+
+    describe('cancelSubscriptionTrial', function () {
+        const mockSubscription = {
+            id: 'sub_123'
+        };
+        beforeEach(function () {
+            mockStripe = {
+                subscriptions: {
+                    update: sinon.stub().resolves(mockSubscription)
+                }
+            };
+            const mockStripeConstructor = sinon.stub().returns(mockStripe);
+            StripeAPI.__set__('Stripe', mockStripeConstructor);
+            api.configure({
+                secretKey: ''
+            });
+        });
+
+        afterEach(function () {
+            sinon.restore();
+        });
+
+        it('cancels a subscription trial', async function () {
+            const result = await api.cancelSubscriptionTrial(mockSubscription.id);
+
+            should.equal(mockStripe.subscriptions.update.callCount, 1);
+
+            should.equal(mockStripe.subscriptions.update.args[0][0], mockSubscription.id);
+            should.deepEqual(mockStripe.subscriptions.update.args[0][1], {trial_end: 'now'});
+
+            should.deepEqual(result, mockSubscription);
+        });
+    });
 });