diff --git a/packages/server/src/routes/index/stripe.test.ts b/packages/server/src/routes/index/stripe.test.ts
index c646f9292e..718ef7588a 100644
--- a/packages/server/src/routes/index/stripe.test.ts
+++ b/packages/server/src/routes/index/stripe.test.ts
@@ -7,7 +7,7 @@ import { AppContext } from '../../utils/types';
 import uuidgen from '../../utils/uuidgen';
 import { postHandlers } from './stripe';
 
-function mockStripe() {
+function mockStripe(overrides: any = null) {
 	return {
 		customers: {
 			retrieve: jest.fn(),
@@ -15,6 +15,7 @@ function mockStripe() {
 		subscriptions: {
 			del: jest.fn(),
 		},
+		...overrides,
 	};
 }
 
@@ -22,6 +23,7 @@ interface WebhookOptions {
 	stripe?: any;
 	eventId?: string;
 	subscriptionId?: string;
+	customerId?: string;
 	sessionId?: string;
 }
 
@@ -44,6 +46,7 @@ async function simulateWebhook(ctx: AppContext, type: string, object: any, optio
 async function createUserViaSubscription(ctx: AppContext, userEmail: string, options: WebhookOptions = {}) {
 	options = {
 		subscriptionId: `sub_${uuidgen()}`,
+		customerId: `cus_${uuidgen()}`,
 		...options,
 	};
 
@@ -53,7 +56,7 @@ async function createUserViaSubscription(ctx: AppContext, userEmail: string, opt
 
 	await simulateWebhook(ctx, 'checkout.session.completed', {
 		id: stripeSessionId,
-		customer: `cus_${uuidgen()}`,
+		customer: options.customerId,
 		subscription: options.subscriptionId,
 		customer_details: {
 			email: userEmail,
@@ -214,4 +217,92 @@ describe('index/stripe', function() {
 		expect(user.can_upload).toBe(1);
 	});
 
+	test('should attach new sub to existing user', async function() {
+		// Simulates:
+		// - User subscribes
+		// - Later the subscription is cancelled, either automatically by Stripe or manually
+		// - Then a new subscription is attached to the user on Stripe
+		// => In that case, the sub should be attached to the user on Joplin Server
+
+		const stripe = mockStripe({
+			customers: {
+				retrieve: async () => {
+					return {
+						name: 'Toto',
+						email: 'toto@example.com',
+					};
+				},
+			},
+		});
+
+		const ctx = await koaAppContext();
+
+		await createUserViaSubscription(ctx, 'toto@example.com', {
+			stripe,
+			subscriptionId: 'sub_1',
+			customerId: 'cus_toto',
+		});
+		await simulateWebhook(ctx, 'customer.subscription.deleted', { id: 'sub_1' });
+
+		const stripePrice = findPrice(stripeConfig().prices, { accountType: 1, period: PricePeriod.Monthly });
+
+		await simulateWebhook(ctx, 'customer.subscription.created', {
+			id: 'sub_new',
+			customer: 'cus_toto',
+			items: { data: [{ price: { id: stripePrice.id } }] },
+		}, { stripe });
+
+		const user = (await models().user().all())[0];
+		const sub = await models().subscription().byUserId(user.id);
+
+		expect(sub.stripe_user_id).toBe('cus_toto');
+		expect(sub.stripe_subscription_id).toBe('sub_new');
+	});
+
+	test('should not cancel a subscription as duplicate if it is already associated with a user', async function() {
+		// When user goes through a Stripe checkout, we get the following
+		// events:
+		//
+		// - checkout.session.completed
+		// - customer.subscription.created
+		//
+		// However we create the subscription as soon as we get
+		// "checkout.session.completed", because by then we already have all the
+		// necessary information. The problem is that Stripe is then going to
+		// send "customer.subscription.created", even though the sub is already
+		// created. Also we have some code to cancel duplicate subscriptions
+		// (when a user accidentally subscribe multiple times), and we don't
+		// want that newly, valid, subscription to be cancelled as a duplicate.
+
+		const stripe = mockStripe({
+			customers: {
+				retrieve: async () => {
+					return {
+						name: 'Toto',
+						email: 'toto@example.com',
+					};
+				},
+			},
+		});
+
+		const ctx = await koaAppContext();
+
+		await createUserViaSubscription(ctx, 'toto@example.com', {
+			stripe,
+			subscriptionId: 'sub_1',
+			customerId: 'cus_toto',
+		});
+
+		const stripePrice = findPrice(stripeConfig().prices, { accountType: 1, period: PricePeriod.Monthly });
+
+		await simulateWebhook(ctx, 'customer.subscription.created', {
+			id: 'sub_1',
+			customer: 'cus_toto',
+			items: { data: [{ price: { id: stripePrice.id } }] },
+		}, { stripe });
+
+		// Verify that we didn't try to delete that new subscription
+		expect(stripe.subscriptions.del).toHaveBeenCalledTimes(0);
+	});
+
 });
diff --git a/packages/server/src/routes/index/stripe.ts b/packages/server/src/routes/index/stripe.ts
index 1d357e70c1..5514066126 100644
--- a/packages/server/src/routes/index/stripe.ts
+++ b/packages/server/src/routes/index/stripe.ts
@@ -12,6 +12,7 @@ import { AccountType } from '../../models/UserModel';
 import { betaUserTrialPeriodDays, cancelSubscription, initStripe, isBetaUser, priceIdToAccountType, stripeConfig } from '../../utils/stripe';
 import { Subscription, UserFlagType } from '../../services/database/types';
 import { findPrice, PricePeriod } from '@joplin/lib/utils/joplinCloud';
+import { Models } from '../../models/factory';
 
 const logger = Logger.create('/stripe');
 
@@ -56,6 +57,64 @@ async function getSubscriptionInfo(event: Stripe.Event, ctx: AppContext): Promis
 	return { sub, stripeSub };
 }
 
+export const handleSubscriptionCreated = async (stripe: Stripe, models: Models, customerName: string, userEmail: string, accountType: AccountType, stripeUserId: string, stripeSubscriptionId: string) => {
+	const existingUser = await models.user().loadByEmail(userEmail);
+
+	if (existingUser) {
+		const sub = await models.subscription().byUserId(existingUser.id);
+
+		if (!sub) {
+			logger.info(`Setting up subscription for existing user: ${existingUser.email}`);
+
+			// First set the account type correctly (in case the
+			// user also upgraded or downgraded their account).
+			await models.user().save({
+				id: existingUser.id,
+				account_type: accountType,
+			});
+
+			// Also clear any payment and subscription related flags
+			// since if we're here it means payment was successful
+			await models.userFlag().removeMulti(existingUser.id, [
+				UserFlagType.FailedPaymentWarning,
+				UserFlagType.FailedPaymentFinal,
+				UserFlagType.SubscriptionCancelled,
+				UserFlagType.AccountWithoutSubscription,
+			]);
+
+			// Then save the subscription
+			await models.subscription().save({
+				user_id: existingUser.id,
+				stripe_user_id: stripeUserId,
+				stripe_subscription_id: stripeSubscriptionId,
+				last_payment_time: Date.now(),
+			});
+		} else {
+			if (sub.stripe_subscription_id === stripeSubscriptionId) {
+				// Stripe probably dispatched a "customer.subscription.created"
+				// event after "checkout.session.completed", so we already have
+				// save the subscription and can skip processing.
+			} else {
+				// The user already has a subscription. Most likely
+				// they accidentally created a second one, so cancel
+				// it.
+				logger.info(`User ${existingUser.email} already has a subscription: ${sub.stripe_subscription_id} - cancelling duplicate`);
+				await cancelSubscription(stripe, stripeSubscriptionId);
+			}
+		}
+	} else {
+		logger.info(`Creating subscription for new user: ${userEmail}`);
+
+		await models.subscription().saveUserAndSubscription(
+			userEmail,
+			customerName,
+			accountType,
+			stripeUserId,
+			stripeSubscriptionId
+		);
+	}
+};
+
 export const postHandlers: PostHandlers = {
 
 	createCheckoutSession: async (stripe: Stripe, __path: SubPath, ctx: AppContext) => {
@@ -172,51 +231,6 @@ export const postHandlers: PostHandlers = {
 				// For testing: `stripe trigger checkout.session.completed`
 				// Or use /checkoutTest URL.
 
-				// {
-				//   "object": {
-				//     "id": "cs_test_xxxxxxxxxxxxxxxxxx",
-				//     "object": "checkout.session",
-				//     "allow_promotion_codes": null,
-				//     "amount_subtotal": 499,
-				//     "amount_total": 499,
-				//     "billing_address_collection": null,
-				//     "cancel_url": "http://joplincloud.local:22300/stripe/cancel",
-				//     "client_reference_id": null,
-				//     "currency": "gbp",
-				//     "customer": "cus_xxxxxxxxxxxx",
-				//     "customer_details": {
-				//       "email": "toto@example.com",
-				//       "tax_exempt": "none",
-				//       "tax_ids": [
-				//       ]
-				//     },
-				//     "customer_email": null,
-				//     "livemode": false,
-				//     "locale": null,
-				//     "metadata": {
-				//     },
-				//     "mode": "subscription",
-				//     "payment_intent": null,
-				//     "payment_method_options": {
-				//     },
-				//     "payment_method_types": [
-				//       "card"
-				//     ],
-				//     "payment_status": "paid",
-				//     "setup_intent": null,
-				//     "shipping": null,
-				//     "shipping_address_collection": null,
-				//     "submit_type": null,
-				//     "subscription": "sub_xxxxxxxxxxxxxxxx",
-				//     "success_url": "http://joplincloud.local:22300/stripe/success?session_id={CHECKOUT_SESSION_ID}",
-				//     "total_details": {
-				//       "amount_discount": 0,
-				//       "amount_shipping": 0,
-				//       "amount_tax": 0
-				//     }
-				//   }
-				// }
-
 				const checkoutSession: Stripe.Checkout.Session = event.data.object as Stripe.Checkout.Session;
 				const userEmail = checkoutSession.customer_details.email || checkoutSession.customer_email;
 
@@ -252,55 +266,41 @@ export const postHandlers: PostHandlers = {
 				const stripeUserId = checkoutSession.customer as string;
 				const stripeSubscriptionId = checkoutSession.subscription as string;
 
-				const existingUser = await models.user().loadByEmail(userEmail);
+				await handleSubscriptionCreated(
+					stripe,
+					models,
+					customerName,
+					userEmail,
+					accountType,
+					stripeUserId,
+					stripeSubscriptionId
+				);
+			},
 
-				if (existingUser) {
-					const sub = await models.subscription().byUserId(existingUser.id);
+			'customer.subscription.created': async () => {
+				const stripeSub: Stripe.Subscription = event.data.object as Stripe.Subscription;
+				const stripeUserId = stripeSub.customer as string;
+				const stripeSubscriptionId = stripeSub.id;
+				const customer = await stripe.customers.retrieve(stripeUserId) as Stripe.Customer;
 
-					if (!sub) {
-						logger.info(`Setting up subscription for existing user: ${existingUser.email}`);
-
-						// First set the account type correctly (in case the
-						// user also upgraded or downgraded their account).
-						await models.user().save({
-							id: existingUser.id,
-							account_type: accountType,
-						});
-
-						// Also clear any payment and subscription related flags
-						// since if we're here it means payment was successful
-						await models.userFlag().removeMulti(existingUser.id, [
-							UserFlagType.FailedPaymentWarning,
-							UserFlagType.FailedPaymentFinal,
-							UserFlagType.SubscriptionCancelled,
-							UserFlagType.AccountWithoutSubscription,
-						]);
-
-						// Then save the subscription
-						await models.subscription().save({
-							user_id: existingUser.id,
-							stripe_user_id: stripeUserId,
-							stripe_subscription_id: stripeSubscriptionId,
-							last_payment_time: Date.now(),
-						});
-					} else {
-						// The user already has a subscription. Most likely
-						// they accidentally created a second one, so cancel
-						// it.
-						logger.info(`User ${existingUser.email} already has a subscription: ${sub.stripe_subscription_id} - cancelling duplicate`);
-						await cancelSubscription(stripe, stripeSubscriptionId);
-					}
-				} else {
-					logger.info(`Creating subscription for new user: ${userEmail}`);
-
-					await models.subscription().saveUserAndSubscription(
-						userEmail,
-						customerName,
-						accountType,
-						stripeUserId,
-						stripeSubscriptionId
-					);
+				let accountType = AccountType.Basic;
+				try {
+					// Really have to dig out the price ID
+					const priceId = stripeSub.items.data[0].price.id;
+					accountType = priceIdToAccountType(priceId);
+				} catch (error) {
+					logger.error('Could not determine account type from price ID - defaulting to "Basic"', error);
 				}
+
+				await handleSubscriptionCreated(
+					stripe,
+					models,
+					customer.name,
+					customer.email,
+					accountType,
+					stripeUserId,
+					stripeSubscriptionId
+				);
 			},
 
 			'invoice.paid': async () => {
diff --git a/packages/server/src/routes/index/users.ts b/packages/server/src/routes/index/users.ts
index c85e62b667..eb73a182a1 100644
--- a/packages/server/src/routes/index/users.ts
+++ b/packages/server/src/routes/index/users.ts
@@ -146,11 +146,11 @@ router.get('users/:id', async (path: SubPath, ctx: AppContext, user: User = null
 		postUrl = `${config().baseUrl}/users/${user.id}`;
 	}
 
-	let userFlags: string[] = isNew ? null : (await models.userFlag().allByUserId(user.id)).map(f => {
+	let userFlags: string[] = isNew ? [] : (await models.userFlag().allByUserId(user.id)).map(f => {
 		return userFlagToString(f);
 	});
 
-	if (!userFlags || !userFlags.length || !owner.is_admin) userFlags = null;
+	if (!owner.is_admin) userFlags = [];
 
 	const subscription = !isNew ? await ctx.joplin.models.subscription().byUserId(userId) : null;
 
@@ -179,6 +179,7 @@ router.get('users/:id', async (path: SubPath, ctx: AppContext, user: User = null
 	view.content.showResetPasswordButton = !isNew && owner.is_admin && user.enabled;
 	view.content.canShareFolderOptions = yesNoDefaultOptions(user, 'can_share_folder');
 	view.content.canUploadOptions = yesNoOptions(user, 'can_upload');
+	view.content.hasFlags = !!userFlags.length;
 	view.content.userFlags = userFlags;
 	view.content.stripePortalUrl = stripePortalUrl();
 
diff --git a/packages/server/src/tools/debugTools.ts b/packages/server/src/tools/debugTools.ts
index b2de24b27f..c0c7855aeb 100644
--- a/packages/server/src/tools/debugTools.ts
+++ b/packages/server/src/tools/debugTools.ts
@@ -93,6 +93,7 @@ export async function createTestUsers(db: DbConnection, config: Config, options:
 			});
 
 			await models.userFlag().add(user.id, UserFlagType.AccountOverLimit);
+			await models.userFlag().add(user.id, UserFlagType.FailedPaymentWarning);
 		}
 	}
 }
diff --git a/packages/server/src/views/index/user.mustache b/packages/server/src/views/index/user.mustache
index d3435aff24..bcf88b5e7d 100644
--- a/packages/server/src/views/index/user.mustache
+++ b/packages/server/src/views/index/user.mustache
@@ -140,16 +140,16 @@
 		</div>
 	{{/subscription}}
 
-	{{#userFlags}}
-		<h1 class="title">Flags</h1>
-	{{/userFlags}}
-	
-	{{#userFlags}}
-		<ul>
-			<li>{{.}}</li>
-		</ul>
-	{{/userFlags}}
-	
+	{{#hasFlags}}
+		<div class="content">
+			<h1 class="title">Flags</h1>
+			{{#userFlags}}
+				<ul>
+					<li>{{.}}</li>
+				</ul>
+			{{/userFlags}}
+		</div>
+	{{/hasFlags}}	
 
 </form>