diff --git a/test/e2e-api/members/webhooks.test.js b/test/e2e-api/members/webhooks.test.js
index 0f2e057af8..c393598868 100644
--- a/test/e2e-api/members/webhooks.test.js
+++ b/test/e2e-api/members/webhooks.test.js
@@ -1,7 +1,10 @@
+const assert = require('assert');
+const nock = require('nock');
 const stripe = require('stripe');
 const {agentProvider, mockManager, fixtureManager} = require('../../utils/e2e-framework');
 
-let agent;
+let membersAgent;
+let adminAgent;
 
 describe('Members API', function () {
     before(async function () {
@@ -11,8 +14,10 @@ describe('Members API', function () {
         // And it's initialised at boot - so mocking it before
         // Probably wanna replace this with a settinfs fixture mock or smth??
         mockManager.setupStripe();
-        agent = await agentProvider.getMembersAPIAgent();
+        membersAgent = await agentProvider.getMembersAPIAgent();
+        adminAgent = await agentProvider.getAdminAPIAgent();
         await fixtureManager.init('members');
+        await adminAgent.loginAsOwner();
     });
 
     beforeEach(function () {
@@ -26,13 +31,13 @@ describe('Members API', function () {
     });
 
     it('Can communicate with the frontend Members API', async function () {
-        await agent.get('/api/site/')
+        await membersAgent.get('/api/site/')
             .expectStatus(200);
     });
 
     describe('/webhooks/stripe/', function () {
         it('Responds with a 401 when the signature is invalid', async function () {
-            await agent.post('/webhooks/stripe/')
+            await membersAgent.post('/webhooks/stripe/')
                 .body({
                     fake: 'data'
                 })
@@ -52,10 +57,108 @@ describe('Members API', function () {
                 secret: process.env.WEBHOOK_SECRET
             });
 
-            await agent.post('/webhooks/stripe/')
+            await membersAgent.post('/webhooks/stripe/')
                 .body(webhookPayload)
                 .header('stripe-signature', webhookSignature)
                 .expectStatus(200);
         });
+
+        describe('checkout.session.completed', function () {
+            it('Will create a member if one does not exist', async function () {
+                const webhookPayload = JSON.stringify({
+                    type: 'checkout.session.completed',
+                    data: {
+                        object: {
+                            mode: 'subscription',
+                            customer: 'cus_123',
+                            subscription: 'sub_123',
+                            metadata: {}
+                        }
+                    }
+                });
+
+                const webhookSignature = stripe.webhooks.generateTestHeaderString({
+                    payload: webhookPayload,
+                    secret: process.env.WEBHOOK_SECRET
+                });
+
+                const subscription = {
+                    id: 'sub_123',
+                    customer: 'cus_123',
+                    status: 'active',
+                    items: {
+                        type: 'list',
+                        data: [{
+                            id: 'item_123',
+                            price: {
+                                id: 'price_123',
+                                product: 'product_123',
+                                active: true,
+                                nickname: 'Monthly',
+                                currency: 'USD',
+                                recurring: {
+                                    interval: 'month'
+                                },
+                                unit_amount: 500,
+                                type: 'recurring'
+                            }
+                        }]
+                    },
+                    start_date: Date.now() / 1000,
+                    current_period_end: Date.now() / 1000 + (60 * 60 * 24 * 31),
+                    cancel_at_period_end: false
+                };
+
+                const customer = {
+                    id: 'cus_123',
+                    name: 'Test Member',
+                    email: 'checkout-webhook-test@email.com',
+                    subscriptions: {
+                        type: 'list',
+                        data: [subscription]
+                    }
+                };
+
+                nock('https://api.stripe.com')
+                    .persist()
+                    .get(/v1\/.*/)
+                    .reply((uri, body) => {
+                        const [match, resource, id] = uri.match(/\/?v1\/(\w+)\/?(\w+)/) || [null];
+
+                        if (!match) {
+                            return [500];
+                        }
+
+                        if (resource === 'customers') {
+                            return [200, customer];
+                        }
+
+                        if (resource === 'subscriptions') {
+                            return [200, subscription];
+                        }
+                    });
+
+                { // ensure member didn't already exist
+                    const {body} = await adminAgent.get('/members/?search=checkout-webhook-test@email.com');
+                    assert.equal(body.members.length, 0, 'A member already existed');
+                }
+
+                await membersAgent.post('/webhooks/stripe/')
+                    .body(webhookPayload)
+                    .header('stripe-signature', webhookSignature);
+
+                const {body} = await adminAgent.get('/members/?search=checkout-webhook-test@email.com');
+                assert.equal(body.members.length, 1, 'The member was not created');
+                const member = body.members[0];
+
+                assert.equal(member.status, 'paid', 'The member should be "paid"');
+                assert.equal(member.subscriptions.length, 1, 'The member should have a single subscription');
+
+                mockManager.assert.sentEmail({
+                    subject: '🙌 Thank you for signing up to Ghost!',
+                    to: 'checkout-webhook-test@email.com'
+                });
+            });
+        });
     });
 });