diff --git a/packages/backend/src/controllers/paddle/webhooks.ee.ts b/packages/backend/src/controllers/paddle/webhooks.ee.ts
index 41ed90da..bd8ebb2d 100644
--- a/packages/backend/src/controllers/paddle/webhooks.ee.ts
+++ b/packages/backend/src/controllers/paddle/webhooks.ee.ts
@@ -12,6 +12,10 @@ export default async (request: IRequest, response: Response) => {
 
   if (request.body.alert_name === 'subscription_created') {
     await Billing.webhooks.handleSubscriptionCreated(request);
+  } else if (request.body.alert_name === 'subscription_updated') {
+    await Billing.webhooks.handleSubscriptionUpdated(request);
+  } else if (request.body.alert_name === 'subscription_cancelled') {
+    await Billing.webhooks.handleSubscriptionCancelled(request);
   } else if (request.body.alert_name === 'subscription_payment_succeeded') {
     await Billing.webhooks.handleSubscriptionPaymentSucceeded(request);
   }
diff --git a/packages/backend/src/db/migrations/20230402183738_add_subscription_id_in_usage_data.ts b/packages/backend/src/db/migrations/20230402183738_add_subscription_id_in_usage_data.ts
new file mode 100644
index 00000000..e2018caf
--- /dev/null
+++ b/packages/backend/src/db/migrations/20230402183738_add_subscription_id_in_usage_data.ts
@@ -0,0 +1,18 @@
+import { Knex } from 'knex';
+import appConfig from '../../config/app';
+
+export async function up(knex: Knex): Promise<void> {
+  if (!appConfig.isCloud) return;
+
+  return knex.schema.table('usage_data', (table) => {
+    table.uuid('subscription_id').references('id').inTable('subscriptions');
+  });
+}
+
+export async function down(knex: Knex): Promise<void> {
+  if (!appConfig.isCloud) return;
+
+  return knex.schema.table('usage_data', (table) => {
+    table.dropColumn('subscription_id');
+  });
+}
diff --git a/packages/backend/src/graphql/queries/get-billing-and-usage.ee.ts b/packages/backend/src/graphql/queries/get-billing-and-usage.ee.ts
index ae6ed957..7c786b96 100644
--- a/packages/backend/src/graphql/queries/get-billing-and-usage.ee.ts
+++ b/packages/backend/src/graphql/queries/get-billing-and-usage.ee.ts
@@ -13,7 +13,7 @@ const getBillingAndUsage = async (
   context: Context
 ) => {
   const persistedSubscription = await context.currentUser.$relatedQuery(
-    'subscription'
+    'currentSubscription'
   );
 
   const subscription = persistedSubscription
@@ -39,8 +39,8 @@ const paidSubscription = (subscription: Subscription): TSubscription => {
       title: currentPlan.limit,
       action: {
         type: 'link',
-        text: 'Change plan',
-        src: '/settings/billing/change-plan',
+        text: 'Cancel plan',
+        src: subscription.cancelUrl,
       },
     },
     nextBillAmount: {
diff --git a/packages/backend/src/graphql/queries/get-invoices.ee.ts b/packages/backend/src/graphql/queries/get-invoices.ee.ts
index c745a4c6..49bad7c5 100644
--- a/packages/backend/src/graphql/queries/get-invoices.ee.ts
+++ b/packages/backend/src/graphql/queries/get-invoices.ee.ts
@@ -6,7 +6,7 @@ const getInvoices = async (
   _params: unknown,
   context: Context
 ) => {
-  const subscription = await context.currentUser.$relatedQuery('subscription');
+  const subscription = await context.currentUser.$relatedQuery('currentSubscription');
 
   if (!subscription) {
     return;
diff --git a/packages/backend/src/graphql/queries/get-trial-status.ee.ts b/packages/backend/src/graphql/queries/get-trial-status.ee.ts
new file mode 100644
index 00000000..58a8f936
--- /dev/null
+++ b/packages/backend/src/graphql/queries/get-trial-status.ee.ts
@@ -0,0 +1,19 @@
+import appConfig from '../../config/app';
+import Context from '../../types/express/context';
+
+const getTrialStatus = async (
+  _parent: unknown,
+  _params: unknown,
+  context: Context
+) => {
+  if (!appConfig.isCloud) return;
+
+  const inTrial = await context.currentUser.inTrial();
+  if (!inTrial) return;
+
+  return {
+    expireAt: context.currentUser.trialExpiryDate,
+  };
+};
+
+export default getTrialStatus;
diff --git a/packages/backend/src/graphql/queries/get-usage-data.ee.ts b/packages/backend/src/graphql/queries/get-usage-data.ee.ts
index a5dfc69b..40f604a3 100644
--- a/packages/backend/src/graphql/queries/get-usage-data.ee.ts
+++ b/packages/backend/src/graphql/queries/get-usage-data.ee.ts
@@ -1,6 +1,7 @@
 import appConfig from '../../config/app';
 import Context from '../../types/express/context';
 
+// TODO: remove as getBillingAndUsageData query has been introduced
 const getUsageData = async (
   _parent: unknown,
   _params: unknown,
@@ -9,18 +10,20 @@ const getUsageData = async (
   if (!appConfig.isCloud) return;
 
   const usageData = await context.currentUser
-    .$relatedQuery('usageData')
+    .$relatedQuery('currentUsageData')
     .throwIfNotFound();
 
-  const paymentPlan = await context.currentUser
-    .$relatedQuery('paymentPlan')
+  const subscription = await usageData
+    .$relatedQuery('subscription')
     .throwIfNotFound();
 
+  const plan = subscription.plan;
+
   const computedUsageData = {
-    name: paymentPlan.name,
-    allowedTaskCount: paymentPlan.taskCount,
+    name: plan.name,
+    allowedTaskCount: plan.quota,
     consumedTaskCount: usageData.consumedTaskCount,
-    remainingTaskCount: paymentPlan.taskCount - usageData.consumedTaskCount,
+    remainingTaskCount: plan.quota - usageData.consumedTaskCount,
     nextResetAt: usageData.nextResetAt,
   };
 
diff --git a/packages/backend/src/graphql/query-resolvers.ts b/packages/backend/src/graphql/query-resolvers.ts
index b7263799..71e44020 100644
--- a/packages/backend/src/graphql/query-resolvers.ts
+++ b/packages/backend/src/graphql/query-resolvers.ts
@@ -17,6 +17,7 @@ import getPaddleInfo from './queries/get-paddle-info.ee';
 import getBillingAndUsage from './queries/get-billing-and-usage.ee';
 import getInvoices from './queries/get-invoices.ee';
 import getAutomatischInfo from './queries/get-automatisch-info';
+import getTrialStatus from './queries/get-trial-status.ee';
 import healthcheck from './queries/healthcheck';
 
 const queryResolvers = {
@@ -39,6 +40,7 @@ const queryResolvers = {
   getBillingAndUsage,
   getInvoices,
   getAutomatischInfo,
+  getTrialStatus,
   healthcheck,
 };
 
diff --git a/packages/backend/src/graphql/schema.graphql b/packages/backend/src/graphql/schema.graphql
index 458abe2e..2ffe0fcd 100644
--- a/packages/backend/src/graphql/schema.graphql
+++ b/packages/backend/src/graphql/schema.graphql
@@ -40,6 +40,7 @@ type Query {
   getBillingAndUsage: GetBillingAndUsage
   getInvoices: [Invoice]
   getAutomatischInfo: GetAutomatischInfo
+  getTrialStatus: GetTrialStatus
   healthcheck: AppHealth
 }
 
@@ -475,6 +476,10 @@ type GetAutomatischInfo {
   isCloud: Boolean
 }
 
+type GetTrialStatus {
+  expireAt: String
+}
+
 type GetBillingAndUsage {
   subscription: Subscription
   usage: Usage
diff --git a/packages/backend/src/helpers/billing/paddle.ee.ts b/packages/backend/src/helpers/billing/paddle.ee.ts
index 40594016..f558713d 100644
--- a/packages/backend/src/helpers/billing/paddle.ee.ts
+++ b/packages/backend/src/helpers/billing/paddle.ee.ts
@@ -24,6 +24,7 @@ const getSubscription = async (subscriptionId: number) => {
 };
 
 const getInvoices = async (subscriptionId: number) => {
+  // TODO: iterate over previous subscriptions and include their invoices
   const data = {
     vendor_id: appConfig.paddleVendorId,
     vendor_auth_code: appConfig.paddleVendorAuthCode,
diff --git a/packages/backend/src/helpers/billing/plans.ee.ts b/packages/backend/src/helpers/billing/plans.ee.ts
index 98bdcac9..45b2fea5 100644
--- a/packages/backend/src/helpers/billing/plans.ee.ts
+++ b/packages/backend/src/helpers/billing/plans.ee.ts
@@ -2,15 +2,14 @@ const plans = [
   {
     name: '10k - monthly',
     limit: '10,000',
+    quota: 10000,
     price: '€20',
     productId: '47384',
-  },
-  {
-    name: '30k - monthly',
-    limit: '30,000',
-    price: '€50',
-    productId: '47419',
-  },
+  }
 ];
 
+export function getPlanById(id: string) {
+  return plans.find((plan) => plan.productId === id);
+}
+
 export default plans;
diff --git a/packages/backend/src/helpers/billing/webhooks.ee.ts b/packages/backend/src/helpers/billing/webhooks.ee.ts
index 46930a8e..056c754f 100644
--- a/packages/backend/src/helpers/billing/webhooks.ee.ts
+++ b/packages/backend/src/helpers/billing/webhooks.ee.ts
@@ -3,7 +3,30 @@ import Subscription from '../../models/subscription.ee';
 import Billing from './index.ee';
 
 const handleSubscriptionCreated = async (request: IRequest) => {
-  await Subscription.query().insertAndFetch(formatSubscription(request));
+  const subscription = await Subscription.query().insertAndFetch(formatSubscription(request));
+  await subscription.$relatedQuery('usageData').insert(formatUsageData(request));
+};
+
+const handleSubscriptionUpdated = async (request: IRequest) => {
+  await Subscription
+    .query()
+    .findOne({
+      paddle_subscription_id: request.body.subscription_id,
+    })
+    .patch(formatSubscription(request));
+};
+
+const handleSubscriptionCancelled = async (request: IRequest) => {
+  const subscription = await Subscription
+    .query()
+    .findOne({
+      paddle_subscription_id: request.body.subscription_id,
+    })
+    .patchAndFetch(formatSubscription(request));
+
+  if (request.body.status === 'deleted') {
+    await subscription.$query().delete();
+  }
 };
 
 const handleSubscriptionPaymentSucceeded = async (request: IRequest) => {
@@ -22,6 +45,8 @@ const handleSubscriptionPaymentSucceeded = async (request: IRequest) => {
     nextBillDate: remoteSubscription.next_payment.date,
     lastBillDate: remoteSubscription.last_payment.date,
   });
+
+  await subscription.$relatedQuery('usageData').insert(formatUsageData(request));
 };
 
 const formatSubscription = (request: IRequest) => {
@@ -37,8 +62,18 @@ const formatSubscription = (request: IRequest) => {
   };
 };
 
+const formatUsageData = (request: IRequest) => {
+  return {
+    userId: JSON.parse(request.body.passthrough).id,
+    consumedTaskCount: 0,
+    nextResetAt: request.body.next_bill_date,
+  };
+};
+
 const webhooks = {
   handleSubscriptionCreated,
+  handleSubscriptionUpdated,
+  handleSubscriptionCancelled,
   handleSubscriptionPaymentSucceeded,
 };
 
diff --git a/packages/backend/src/models/execution-step.ts b/packages/backend/src/models/execution-step.ts
index 6b52d15d..b26a3766 100644
--- a/packages/backend/src/models/execution-step.ts
+++ b/packages/backend/src/models/execution-step.ts
@@ -67,7 +67,7 @@ class ExecutionStep extends Base {
       if (!execution.testRun && !this.isFailed) {
         const flow = await execution.$relatedQuery('flow');
         const user = await flow.$relatedQuery('user');
-        const usageData = await user.$relatedQuery('usageData');
+        const usageData = await user.$relatedQuery('currentUsageData');
 
         await usageData.increaseConsumedTaskCountByOne();
       }
diff --git a/packages/backend/src/models/flow.ts b/packages/backend/src/models/flow.ts
index 6eaab50f..ed57c1f3 100644
--- a/packages/backend/src/models/flow.ts
+++ b/packages/backend/src/models/flow.ts
@@ -136,7 +136,7 @@ class Flow extends Base {
     if (!appConfig.isCloud) return;
 
     const user = await this.$relatedQuery('user');
-    const usageData = await user.$relatedQuery('usageData');
+    const usageData = await user.$relatedQuery('currentUsageData');
 
     const hasExceeded = await usageData.checkIfLimitExceeded();
 
diff --git a/packages/backend/src/models/subscription.ee.ts b/packages/backend/src/models/subscription.ee.ts
index 5cadc24b..216e5e52 100644
--- a/packages/backend/src/models/subscription.ee.ts
+++ b/packages/backend/src/models/subscription.ee.ts
@@ -1,5 +1,7 @@
 import Base from './base';
 import User from './user';
+import UsageData from './usage-data.ee';
+import { getPlanById } from '../helpers/billing/plans.ee';
 
 class Subscription extends Base {
   id!: string;
@@ -12,6 +14,8 @@ class Subscription extends Base {
   nextBillAmount!: string;
   nextBillDate!: string;
   lastBillDate?: string;
+  usageData?: UsageData[];
+  currentUsageData?: UsageData;
 
   static tableName = 'subscriptions';
 
@@ -51,7 +55,31 @@ class Subscription extends Base {
         to: 'users.id',
       },
     },
+    usageData: {
+      relation: Base.HasManyRelation,
+      modelClass: UsageData,
+      join: {
+        from: 'subscriptions.id',
+        to: 'usage_data.subscription_id',
+      },
+    },
+    currentUsageData: {
+      relation: Base.HasOneRelation,
+      modelClass: UsageData,
+      join: {
+        from: 'subscriptions.id',
+        to: 'usage_data.subscription_id',
+      },
+    },
   });
+
+  get plan() {
+    return getPlanById(this.paddlePlanId);
+  }
+
+  get isActive() {
+    return this.status === 'active' || this.status === 'past_due';
+  }
 }
 
 export default Subscription;
diff --git a/packages/backend/src/models/usage-data.ee.ts b/packages/backend/src/models/usage-data.ee.ts
index 2e508f12..047d0bf1 100644
--- a/packages/backend/src/models/usage-data.ee.ts
+++ b/packages/backend/src/models/usage-data.ee.ts
@@ -1,14 +1,17 @@
 import { raw } from 'objection';
 import Base from './base';
 import User from './user';
-import PaymentPlan from './payment-plan.ee';
+import Subscription from './subscription.ee';
+import { getPlanById } from '../helpers/billing/plans.ee';
 
 class UsageData extends Base {
   id!: string;
   userId!: string;
+  subscriptionId?: string;
   consumedTaskCount!: number;
   nextResetAt!: string;
-  paymentPlan?: PaymentPlan;
+  subscription?: Subscription;
+  user?: User;
 
   static tableName = 'usage_data';
 
@@ -19,6 +22,7 @@ class UsageData extends Base {
     properties: {
       id: { type: 'string', format: 'uuid' },
       userId: { type: 'string', format: 'uuid' },
+      subscriptionId: { type: 'string', format: 'uuid' },
       consumedTaskCount: { type: 'integer' },
       nextResetAt: { type: 'string' },
     },
@@ -33,24 +37,38 @@ class UsageData extends Base {
         to: 'users.id',
       },
     },
-    paymentPlan: {
+    subscription: {
       relation: Base.BelongsToOneRelation,
-      modelClass: PaymentPlan,
+      modelClass: Subscription,
       join: {
-        from: 'usage_data.user_id',
-        to: 'payment_plans.user_id',
+        from: 'usage_data.subscription_id',
+        to: 'subscriptions.id',
       },
     },
   });
 
   async checkIfLimitExceeded() {
-    const paymentPlan = await this.$relatedQuery('paymentPlan');
+    const user = await this.$relatedQuery('user');
 
-    return this.consumedTaskCount >= paymentPlan.taskCount;
+    if (await user.inTrial()) {
+      return false;
+    }
+
+    const subscription = await this.$relatedQuery('subscription');
+
+    if (!subscription.isActive) {
+      return true;
+    }
+
+    const plan = subscription.plan;
+
+    return this.consumedTaskCount >= plan.quota;
   }
 
   async increaseConsumedTaskCountByOne() {
-    return await this.$query().patch({ consumedTaskCount: raw('consumed_task_count + 1') });
+    return await this.$query().patch({
+      consumedTaskCount: raw('consumed_task_count + 1'),
+    });
   }
 }
 
diff --git a/packages/backend/src/models/user.ts b/packages/backend/src/models/user.ts
index 3815e693..f83b6c01 100644
--- a/packages/backend/src/models/user.ts
+++ b/packages/backend/src/models/user.ts
@@ -1,15 +1,14 @@
 import { QueryContext, ModelOptions } from 'objection';
+import bcrypt from 'bcrypt';
+import crypto from 'crypto';
 import { DateTime } from 'luxon';
 import appConfig from '../config/app';
 import Base from './base';
+import ExtendedQueryBuilder from './query-builder';
 import Connection from './connection';
 import Flow from './flow';
 import Step from './step';
 import Execution from './execution';
-import ExecutionStep from './execution-step';
-import bcrypt from 'bcrypt';
-import crypto from 'crypto';
-import PaymentPlan from './payment-plan.ee';
 import UsageData from './usage-data.ee';
 import Subscription from './subscription.ee';
 
@@ -26,9 +25,10 @@ class User extends Base {
   flows?: Flow[];
   steps?: Step[];
   executions?: Execution[];
-  paymentPlan?: PaymentPlan;
-  usageData?: UsageData;
-  subscription?: Subscription;
+  usageData?: UsageData[];
+  currentUsageData?: UsageData;
+  subscriptions?: Subscription[];
+  currentSubscription?: Subscription;
 
   static tableName = 'users';
 
@@ -86,29 +86,43 @@ class User extends Base {
         to: 'executions.flow_id',
       },
     },
-    paymentPlan: {
-      relation: Base.HasOneRelation,
-      modelClass: PaymentPlan,
-      join: {
-        from: 'payment_plans.user_id',
-        to: 'users.id',
-      },
-    },
     usageData: {
-      relation: Base.HasOneRelation,
+      relation: Base.HasManyRelation,
       modelClass: UsageData,
       join: {
         from: 'usage_data.user_id',
         to: 'users.id',
       },
     },
-    subscription: {
+    currentUsageData: {
+      relation: Base.HasOneRelation,
+      modelClass: UsageData,
+      join: {
+        from: 'usage_data.user_id',
+        to: 'users.id',
+      },
+      filter(builder: ExtendedQueryBuilder<UsageData>) {
+        builder.orderBy('created_at', 'desc').first();
+      },
+    },
+    subscriptions: {
+      relation: Base.HasManyRelation,
+      modelClass: Subscription,
+      join: {
+        from: 'subscriptions.user_id',
+        to: 'users.id',
+      },
+    },
+    currentSubscription: {
       relation: Base.HasOneRelation,
       modelClass: Subscription,
       join: {
         from: 'subscriptions.user_id',
         to: 'users.id',
       },
+      filter(builder: ExtendedQueryBuilder<Subscription>) {
+        builder.orderBy('created_at', 'desc').first();
+      },
     },
   });
 
@@ -151,6 +165,29 @@ class User extends Base {
     this.trialExpiryDate = DateTime.now().plus({ days: 30 }).toISODate();
   }
 
+  async inTrial() {
+    if (!appConfig.isCloud) {
+      return false;
+    }
+
+    if (!this.trialExpiryDate) {
+      return false;
+    }
+
+    const subscription = await this.$relatedQuery('currentSubscription');
+
+    if (subscription?.isActive) {
+      return false;
+    }
+
+    const expiryDate = DateTime.fromJSDate(
+      this.trialExpiryDate as unknown as Date
+    );
+    const now = DateTime.now();
+
+    return now < expiryDate;
+  }
+
   async $beforeInsert(queryContext: QueryContext) {
     await super.$beforeInsert(queryContext);
     await this.generateHash();
@@ -167,6 +204,18 @@ class User extends Base {
       await this.generateHash();
     }
   }
+
+  async $afterInsert(queryContext: QueryContext) {
+    await super.$afterInsert(queryContext);
+
+    if (appConfig.isCloud) {
+      await this.$relatedQuery('usageData').insert({
+        userId: this.id,
+        consumedTaskCount: 0,
+        nextResetAt: DateTime.now().plus({ days: 30 }).toISODate(),
+      });
+    }
+  }
 }
 
 export default User;
diff --git a/packages/backend/src/routes/paddle.ee.ts b/packages/backend/src/routes/paddle.ee.ts
index 46e96b65..3f6aa004 100644
--- a/packages/backend/src/routes/paddle.ee.ts
+++ b/packages/backend/src/routes/paddle.ee.ts
@@ -6,13 +6,13 @@ const router = Router();
 
 const exposeError =
   (handler: RequestHandler) =>
-  async (req: IRequest, res: Response, next: NextFunction) => {
-    try {
-      await handler(req, res, next);
-    } catch (err) {
-      next(err);
-    }
-  };
+    async (req: IRequest, res: Response, next: NextFunction) => {
+      try {
+        await handler(req, res, next);
+      } catch (err) {
+        next(err);
+      }
+    };
 
 router.post('/webhooks', exposeError(webhooksHandler));
 
diff --git a/packages/web/src/components/UsageDataInformation/index.ee.tsx b/packages/web/src/components/UsageDataInformation/index.ee.tsx
index b2162001..4cd47a2f 100644
--- a/packages/web/src/components/UsageDataInformation/index.ee.tsx
+++ b/packages/web/src/components/UsageDataInformation/index.ee.tsx
@@ -191,7 +191,8 @@ export default function UsageDataInformation() {
             <Divider sx={{ mt: 2 }} />
           </Box>
 
-          <Button
+          {/* free plan has `null` status so that we can show the upgrade button */}
+          {billingAndUsageData?.subscription?.status === null && <Button
             component={Link}
             to={URLS.SETTINGS_PLAN_UPGRADE}
             size="small"
@@ -199,7 +200,7 @@ export default function UsageDataInformation() {
             sx={{ mt: 2, alignSelf: 'flex-end' }}
           >
             {formatMessage('usageDataInformation.upgrade')}
-          </Button>
+          </Button>}
         </CardContent>
       </Card>
     </React.Fragment>