diff --git a/src/controllers/paymentController.ts b/src/controllers/paymentController.ts
index 7de2ed3..104de72 100644
--- a/src/controllers/paymentController.ts
+++ b/src/controllers/paymentController.ts
@@ -261,6 +261,139 @@ export async function StripeWebhook(req: Request, res: Response) {
       return res.status(400).send(`Webhook Error: ${error}`);
     }
 
+    let userId;
+    let customerId;
+    let user;
+
+    switch (event.type) {
+      case "checkout.session.completed":
+        userId = (event.data.object as Stripe.Checkout.Session)?.metadata
+          ?.userId;
+
+        if (userId === undefined) {
+          logger.error(
+            "StripeWebhook: checkout.session.completed: userId undefined"
+          );
+          break;
+        }
+
+        // delete user pending payment
+
+        const pendingPayment = await UserPendingPayment.findOne({
+          where: {
+            payment_session_id: (event.data.object as Stripe.Checkout.Session)
+              .id,
+          },
+        });
+
+        if (pendingPayment !== null) {
+          await pendingPayment.destroy();
+
+          let user = await User.findOne({
+            where: {
+              user_id: userId,
+            },
+          });
+
+          if (user !== null && user.state === ACCOUNT_STATE.INIT_PAYMENT) {
+            // update user state
+            await User.update(
+              {
+                state: ACCOUNT_STATE.ACTIVE,
+                stripe_customer_id: (
+                  event.data.object as Stripe.Checkout.Session
+                ).customer as string,
+              },
+              {
+                where: {
+                  user_id: userId,
+                },
+              }
+            );
+
+            userLogger.info(
+              userId as string,
+              "StripeWebhook: user state updated to ACTIVE"
+            );
+          }
+        }
+        break;
+      case "checkout.session.expired":
+        logger.info(
+          `StripeWebhook: checkout.session.expired: ${event.data.object.id}`
+        );
+
+        break;
+      case "billing_portal.session.created":
+        customerId = event.data.object.customer as string;
+
+        user = await User.findOne({
+          where: {
+            stripe_customer_id: customerId,
+          },
+        });
+
+        if (user === null) {
+          logger.error(
+            `StripeWebhook: customer.subscription.updated: user not found for customerId: ${customerId}`
+          );
+          break;
+        }
+
+        userLogger.info(
+          user.user_id as string,
+          `StripeWebhook: billing_portal.session.created: customerId: ${customerId}`
+        );
+        break;
+      case "customer.subscription.updated":
+        const subscription = event.data.object as Stripe.Subscription;
+
+        const status = subscription.status;
+        const trialEnd = subscription.trial_end as number | null;
+        const canceledAt = subscription.canceled_at;
+
+        customerId = subscription.customer as string;
+
+        logger.info(
+          `StripeWebhook: customer.subscription.updated: ${subscription.id} status: ${status} trialEnd: ${trialEnd} canceledAt: ${canceledAt} customerId: ${customerId}`
+        );
+
+        user = await User.findOne({
+          where: {
+            stripe_customer_id: customerId,
+          },
+        });
+
+        if (user === null) {
+          logger.error(
+            `StripeWebhook: customer.subscription.updated: user not found for customerId: ${customerId}`
+          );
+          break;
+        }
+
+        let updateData: any = {
+          payment_plan_status: status,
+          payment_plan_trial_end: trialEnd !== null ? trialEnd : null,
+          payment_plan_canceled_at: canceledAt !== null ? canceledAt : null,
+        };
+
+        logger.info(
+          `StripeWebhook: customer.subscription.updated: updating user: ${
+            user.user_id
+          } ${JSON.stringify(updateData)}`
+        );
+
+        await User.update(updateData, {
+          where: {
+            stripe_customer_id: customerId,
+          },
+        });
+        break;
+      default:
+        logger.warn(`StripeWebhook: Ignoring unknown event: ${event.type}`);
+        break;
+    }
+    /*
     if (event.type === "checkout.session.completed") {
       const userId = (event.data.object as Stripe.Checkout.Session)?.metadata
         ?.userId;
@@ -307,11 +440,11 @@ export async function StripeWebhook(req: Request, res: Response) {
       logger.info(`webhook checkout.session.expired: ${event.data.object.id}`);
     } else {
       logger.warn(`Ignoring unknown event: ${event.type}`);
-    }
+    } */
 
     res.sendStatus(200);
   } catch (error) {
-    logger.error("StripeWebhook", error as string);
+    logger.error("StripeWebhook err:", error as string);
     res.status(500).send({ err: "invalid request" });
   }
 }
diff --git a/src/controllers/userController.ts b/src/controllers/userController.ts
index 28bb928..e5f3722 100644
--- a/src/controllers/userController.ts
+++ b/src/controllers/userController.ts
@@ -20,6 +20,7 @@ import {
   CALENDAR_MIN_EARLIEST_BOOKING_TIME,
   EMAIL_VERIFICATION_STATE,
   PAYMENT_PLAN_SETTINGS,
+  PAYMENT_PLAN_STATUS,
   Roles,
   USER_ANALYTICS_ENABLED_DEFAULT,
 } from "../utils/constants";
@@ -175,6 +176,7 @@ export async function SignUp(req: Request, res: Response) {
       analytics_enabled: USER_ANALYTICS_ENABLED_DEFAULT,
       state: ACCOUNT_STATE.INIT_PAYMENT,
       payment_plan: paymentPlan,
+      payment_plan_status: PAYMENT_PLAN_STATUS.TRAILING,
     });
 
     const checkoutSessionUrl = await CreateCheckoutSession(
@@ -449,6 +451,9 @@ export async function GetUser(req: Request, res: Response) {
         "language",
         "analytics_enabled",
         "payment_plan",
+        "payment_plan_status",
+        "payment_plan_trial_end",
+        "payment_plan_canceled_at",
         "created_at",
       ],
     });
@@ -476,10 +481,14 @@ export async function GetUser(req: Request, res: Response) {
         language: user.language,
         analytics_enabled: user.analytics_enabled,
         payment_plan: user.payment_plan,
+        payment_plan_status: user.payment_plan_status,
+        payment_plan_trial_end: user.payment_plan_trial_end,
+        payment_plan_canceled_at: user.payment_plan_canceled_at,
       },
       stores: stores,
       // only temporary until we have a proper permissions system
       permissions: [] as string[],
+      paymentPlanSettings: PAYMENT_PLAN_SETTINGS[user.payment_plan],
     };
 
     // if user is not a store master, then check if user is a worker
@@ -512,6 +521,16 @@ export async function GetUser(req: Request, res: Response) {
       );
     }
 
+    // send error if user has invalid payment plan
+    if (!isPaymentPlanValid(user.payment_plan)) {
+      userLogger.error(
+        session.user_id,
+        `User has invalid payment plan: ${
+          user.payment_plan
+        }. Possible highest payment plan is ${PAYMENT_PLAN_SETTINGS.length - 1}`
+      );
+    }
+
     // update user session last_used
 
     Session.update(
diff --git a/src/models/user.ts b/src/models/user.ts
index 2e543e7..b76598e 100644
--- a/src/models/user.ts
+++ b/src/models/user.ts
@@ -18,6 +18,9 @@ interface UserAttributes {
   google_account_picture?: string;
   analytics_enabled: boolean;
   payment_plan: number;
+  payment_plan_status?: string;
+  payment_plan_trial_end?: number;
+  payment_plan_canceled_at?: number;
   stripe_customer_id?: string;
 }
 
@@ -37,6 +40,9 @@ class User extends Model<UserAttributes> implements UserAttributes {
   declare google_account_picture: string;
   declare analytics_enabled: boolean;
   declare payment_plan: number;
+  declare payment_plan_status: string;
+  declare payment_plan_trial_end: number;
+  declare payment_plan_canceled_at: number;
   declare stripe_customer_id: string;
   declare created_at: Date;
 }
@@ -95,7 +101,7 @@ User.init(
     },
     google_account_picture: {
       type: DataTypes.STRING(1050),
-      allowNull: true, // varchar(1050) needs to be set manually
+      allowNull: true,
     },
     analytics_enabled: {
       type: DataTypes.BOOLEAN,
@@ -105,6 +111,18 @@ User.init(
       type: DataTypes.TINYINT,
       allowNull: false,
     },
+    payment_plan_status: {
+      type: DataTypes.STRING,
+      allowNull: true,
+    },
+    payment_plan_trial_end: {
+      type: DataTypes.INTEGER,
+      allowNull: true,
+    },
+    payment_plan_canceled_at: {
+      type: DataTypes.INTEGER,
+      allowNull: true,
+    },
     stripe_customer_id: {
       type: DataTypes.STRING,
       allowNull: true,
diff --git a/src/utils/constants.ts b/src/utils/constants.ts
index 90dd23f..8083deb 100644
--- a/src/utils/constants.ts
+++ b/src/utils/constants.ts
@@ -89,27 +89,25 @@ export const ACCOUNT_EXPORT_URL = `${DASHBOARD_URL}/api/v1/user/profile/export/`
 export const TERMIN_PLANNER_URL = process.env.TERMIN_PLANNER_URL;
 
 export enum PAYMENT_PLAN {
-  DEMO = 0,
-  BASIC = 1,
-  PREMIUM = 2,
+  BASIC = 0,
+  PREMIUM = 1,
 }
 
 export const PAYMENT_PLAN_SETTINGS = [
   {
-    // demo
-    maxEmployees: 5,
-    calendarMaxFutureBookingDays: 14,
-  },
-  {
-    // basic
-    id: "basic",
+    id: "basic", // used in the backend for identifiying the stripe pricing product
+    name: "Basic", // used in the frontend
     maxEmployees: 15,
     calendarMaxFutureBookingDays: 60,
   },
   {
-    // premium
-    id: "premium",
+    id: "premium", // used in the backend for identifiying the stripe pricing product
+    name: "Premium", // used in the frontend
     maxEmployees: 20,
     calendarMaxFutureBookingDays: 90,
   },
 ];
+
+export enum PAYMENT_PLAN_STATUS {
+  TRAILING = "trailing",
+}
diff --git a/src/validator/validator.ts b/src/validator/validator.ts
index b176f91..b11fd3e 100644
--- a/src/validator/validator.ts
+++ b/src/validator/validator.ts
@@ -184,7 +184,7 @@ export function isCalendarMinEarliestBookingTimeValid(
 
 export function isPaymentPlanValid(paymentPlan: number) {
   return (
-    paymentPlan !== PAYMENT_PLAN.DEMO && paymentPlan <= PAYMENT_PLAN.PREMIUM
+    paymentPlan >= PAYMENT_PLAN.BASIC && paymentPlan <= PAYMENT_PLAN.PREMIUM
   );
 }